1

Mr. Big Police Investigations: The Interrogation Trilogy and Charter Implications

Janaya Dunn

Under the Supervision of
Professor Doug King
An Honours Project submitted in partial fulfilment of the
Degree Requirements for the degree of
Bachelor of Arts – Criminal Justice (Honours)
Mount Royal University

April 2021

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Copyright 2021
Janaya Dunn.
ALL RIGHTS RESERVED

This work is completed in its entirety by Janaya Dunn. All rights are reserved to the information
provided within this document.

MOUNT ROYAL UNIVERSITY
CALGARY, AB. CANADA

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Abstract
Mr. Big operations are a complex undercover investigative technique used to collect evidence on
a suspect with limited evidence to press charges. The particular circumstances and very nature of
a Mr. Big operation has led to considerable criticism regarding the difficulty of law enforcement
being able to balance their independence and oversight concerning the rights of the accused.
Furthermore, significant officer discretion is required. Various investigative strategies that are
used in Mr. Big operations, from threatening the suspect, false presentations of evidence, untrue
promises and enticements, alongside the complete alteration of reality, have demonstrated the
possibility of severe police misconduct. These tactics undeniably raise concerns pertaining to the
reliability of the evidence such as, if the confession was coerced, involuntary, or if the impact of
these aggressive or enticing tactics could lead the suspect to confess falsely. Such techniques
engage the Charter of Rights and Freedoms, section 7 and section 11(d), based on the
fundamental principles of justice; these afforded legal rights are engaged to help protect the
accused from an unreasonable state intrusion. The unique engagement of these rights and Mr.
Big Operations has been addressed in the landmark case of R v Hart [2014], with a new
common-law rule for addressing the reliability and protections of the accused. However, there is
still a prominent lack of oversight and guidance in which there is vast opportunity for harmful
police misconduct, increasing the potential for wrongful convictions and miscarriages of justice.

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Acknowledgements
In dedication to my big brother, Kody.
Thank you for always believing me, even when I couldn’t believe in myself. Your never
wavering support, love, and confidence in me has given me the courage to conquer mountains.
Great things come from the spirit of the one you love; we did this together. Forever and Always.
Thank you to my wonderful parents Mark and Lisa Dunn, and my younger brother
Darien, for selflessly taking every step of this journey along with me. For everything, you have
done and continue to do for me, for all your unconditional love, encouragement, and guidance. I
am forever grateful for the opportunities and experiences that have led me here, for your
countless hugs and all the time you have spent listening to my papers, presentations, and neverending fears and stresses. Thank you for giving me the strength to persevere in the face of a
challenge and for teaching me never to doubt myself. I love you all beyond words.
I would also like to express my deepest gratitude to my Honours supervisor and one of
the most inspiring professors, Doug King, for not only supervising me on this project but for the
continuous support, understanding, and guidance that you have selflessly shown me. It has been
the most enjoyable honour to have been your student throughout my education at Mount Royal
University. Thank you for igniting this “Charter bug” within me, encouraging all my aspirations,
and for all the lasting wonderful ways you have touched my life.
To my beautiful friend Samantha H., thank you for your friendship, for never failing to
lift me up with encouragement and love and for always being willing to listen. I’d also like to
thank my wonderful friends, Cameron H., Courtney U., Courtney M., Kai L., Alessandra G. S.,
& Keshani P. Thank you for always being a genuine light in my life. I’m forever grateful to have
the most inspiring and supportive friends.
Lastly, thank you to the Mount Royal University criminal justice faculty and Dr. Dawn
Rault for the time and guidance you have given me throughout my program. You have gone
above and beyond in sharing opportunities and resources, editing and giving feedback on my
work, and supporting me in my academic journey. I have the utmost respect and appreciation for
my Criminal Justice professors, who have kept me intrigued, determined and helped prepare me
to reach my goals.

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Table of Contents
MR. BIG OPERATIONS AND THE CHARTER

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RESEARCH QUESTION

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METHODOLOGY

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LIMITATIONS

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DEFINING AND EXPLAINING A MR. BIG OPERATION
THE PROCESS OF A MR. BIG OPERATION
CRITICISMS OF MR. BIG OPERATIONS
Producing False Confessions
MR. BIG OPERATIONS AND ENTRAPMENT
R V MACK [1988]
R V HART [2014]
THE INTERROGATION TRILOGY
CONFESSION RULE - R V OICKLE [2000]
RIGHT TO SILENCE - R V HEBERT [1990] AND R V SINGH [2007]
R v Hebert [1990]
R v. Singh [2007]
RIGHT TO COUNSEL – R V SINCLAIR [2010]
CANADIAN CHARTER OF RIGHTS AND FREEDOMS IMPLICATIONS
SECTION 7 OF THE CHARTER: FUNDAMENTAL JUSTICE
Procedural Fundamental Justice Principles: Right to Silence
Violation of Section 7.
Justification under Section 1.
SECTION 11(D) OF THE CHARTER: INNOCENT UNTIL PROVEN GUILTY
R. V. HART [2014]
THE NEW COMMON LAW RULE
LEGAL IMPLICATIONS AND DISCUSSION
INVOLUNTARY OR FALSE CONFESSIONS
ACCUSATORY INTERVIEW STYLE
AURA OF VIOLENCE
INDUCEMENTS FOR A FALSE CONFESSION
PSYCHOLOGICAL STRESS
POLICE OFFICER DISCRETION
ENGAGEMENT OF THE CHARTER OF RIGHTS AND FREEDOMS
RECOMMENDATIONS AND CONCLUSION
RECOMMENDATION ONE
RECOMMENDATION TWO
RECOMMENDATION THREE

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RECOMMENDATION FOUR
RECOMMENDATION FIVE
REFERENCES

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Mr. Big Operations and the Charter
“Mr. Big operations” are an undercover investigative technique used in cases where there
is a lack of evidence required to charge an individual with a crime. Mr. Big represents a
hypothetical crime boss of a criminal syndicate that recruits the accused with the intention of
collecting a confession or further evidence. In actual fact, Mr. Big is an undercover police officer
engaged in an investigation that has, as its goal, the production of a confession. However, these
investigations are often subjected to criticism and debate as these operations hold elements that
risk the possibility of an unreliable or false confession occurring. In upholding the Canadian
Charter of Rights and Freedoms, the rights of the accused must be protected in these
investigations. Tactics such as unreasonable probing, inducements, threats, and violence, may
intrude ones right to silence, right to security of the person, their presumption of innocence, and
the right not to make self-incriminating statements. Over time, there have been a considerable
number of Mr. Big cases that have been appealed and brought to the Supreme Court of Canada
(SCC) where Supreme Court justices must consider the admissibility of evidence obtained
through this undercover technique as they risk posing an unreasonable infringement on the
suspect’s s.7 or s.11(d) Charter rights. Therefore, making the confession or other evidence
collected in the covert investigation inadmissible and would bring the administration of justice
into disrepute.
Research Question
The research question that will be analyzed in this project asks Do Mr. Big Police
operations engage a suspect’s rights concerning section.7 and section.11(d) of the Canadian
Charter of Rights and Freedoms? There is concern that evidence obtained through this technique
can infringe a suspect's s.7 or s.11(d) Charter rights. Law enforcement officers are provided

8
appropriate legal protection to engage in deceptive behaviour to solve serious crimes. However,
one must consider section 24(2) of the Charter of Rights and Freedoms that obliges law
enforcement authorities to “respect all exigencies of the Charter and precludes improperly
obtained evidence from being admitted when it impinges on the fairness of the trial” (Canadian
Charter of Rights and Freedoms, Part I of the Constitution Act, 1982, being Schedule B to the
Canada Act 1982 (U.K.), 1982, c11 s 24(2)). It is crucial to examine this question in order to
identify and determine the extent to which tactics can be used in undercover investigations as
police lies, manipulation, and tricks are discouraged to protect the integrity of the police's
investigation and ethical reliability respecting an individual’s rights. For example, in cases where
Mr. Big operations were used, there is a common theme where judges determined coercion and
entrapment had occurred, placing the suspect in unreasonable circumstances, often causing false
confessions or inadmissible evidence. Mr. Big Operations are still being used as an investigative
strategy today. It is vital to identify the boundaries within these tactics to ensure Charter rights
are protected to the fullest extent to limit miscarriages of justice in the Canadian criminal justice
system.
Methodology
This qualitative analysis aims to describe and clarify the tactics and limitations of
undercover Mr. Big police operations regarding Charter implications. The research design for
this analysis is a mixed-method design that will be “drawing on backgrounds in both the social
sciences and law to carry out this research” (Keenan, & Brockman, 2010, p.27). This analysis
will consist of a case study design and a systematic review design to guide and structure the
found research. Using this interpretive framework will bring forth thoughtful discussion from
findings and generate new understandings and perspectives surrounding the use of Mr. Big

9
Operations, along with the implications they can impose and the risk of a ‘targets’ Charter rights
being unreasonably infringed (USC Libraries, 2020, Mixed Methods Design). The mixedmethod design is valuable to this qualitative study as it allows the exhaustive collection of a
variety of evidence to support the conclusion (USC Libraries, 2020, Mixed Methods Design).
Through the case study design, Supreme Court of Canada cases will be used to identify specific
cases in which Mr. Big Operations were used, bringing judicial insight around circumstances in
which charter rights are unreasonably or reasonably infringed (USC Libraries, 2020, Case Study
Design). The specific cases that will be discussed include R v Hart [2014], R v Mack [1988], and
R v Mack [2014]. The cases of R v Oickle [2000], R v Herbert [1990], and R v Sinclair [2010]
will also be examined regarding the “confession rule” and the right to remain silent to bring
understanding to the police and legal guidelines in obtaining confessions. Using case study
design in this way will contribute to the analysis by providing evidence and rulings from
precedent cases. Using a systematic review design will allow for definition and exploration of
the existing research and criticism around the use of Mr. Big Operations through secondary
research such as peer-reviewed journal articles (USC Libraries, 2020, Systematic Review).
Variables that will be addressed are the investigations where Mr. Big Police Operations
were used, as well as the Charter rights s.7 and s.11(d) to measure if these investigations engage
charter rights and if such engagement could be saved under s.24(2). The specific operational
search terms I will be using pertain to “Mr. Big,” “Mr. Big Police Operations,” “Big Boss,”
“Undercover Crime Boss,” “criticisms of Mr. Big,” “Confession Trilogy,” Infringement, section
7 and section 11 of the Charter, “RCMP and Mr. Big,” and others. Through this unobtrusive
method, pre-existing documents such as journal articles, scholarly publications, and statistics will
be analyzed to provide broader coverage, evidence and knowledge around the topic; the

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inclusion of SCC cases and news articles for data sources (Van Den Hoonaard, 2015, p.126). To
ensure data is being retrieved from reliable sources and is a high-quality source, databases from
the Mount Royal University Library, scholarly sources that the library subscribes to, and other
library resources that librarians have reviewed will be used in search of information (Del Balso,
& Lewis, 2011, p. 49). Using these library sources makes research material convenient and
reliable (Del Balso, & Lewis, 2011, p.51). Scholarly online information sources, including
multidisciplinary databases, will be searched (Del Balso, & Lewis, 2011, p.51). Databases that
will be used are EBSCOhost, PROQUEST, SpringerLink Journals, and CRKN Wiley Online
Library (Mount Royal University, n.d., Databases). Legal Databases such as CanLII, Criminal
Justice Database, and JSTOR will also be searched along with government websites such as
Statistics Canada and RCMP websites. Once the raw data has been collected from these sources,
data will be assessed through content analysis to answer the research question. Content analysis
is a flexible method for examining raw text data and allows for a descriptive and interpretive
framework to be incorporated into this project (Hsieh, & Shannon, 2005, p.1277). This project
will follow the more direct content analysis and extend the existing research on Mr. Big police
operations. Directing focus on determining if these operations unreasonably infringe charter
rights (Hsieh, & Shannon, 2005, p.1281). This methodology provides an opportunity to critically
evaluate and analyze data to explore the research question exhaustively, allowing for findings to
be synthesized, guiding the analysis of whether Mr. Big Operations reasonably or unreasonably
infringe a suspect's Charter rights (USC Libraries, 2020, Systematic Review).
Limitations
Possible limitations of the research design are predominantly concerned with the
exhaustiveness of the research. This is because every case that has used the undercover technique

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of Mr. Big will not be able to be examined due to the fact that not every case that appears before
the judiciary will be entered into a database. For example, it is common for cases where the
accused enters a guilty plea to be excluded from these databases unless a sentencing decision is
published (Keenan, & Brockman, 2010, p.28). There are also cases where Mr. Big Operations
tactics were used in an investigation but may actually be labeled as something other than “Mr.
Big” as in Quebec they are often referred to as “l’opèration d’infiltration” and “un(e) agent(e)
d’infiltration” in which they would be missed in the collection of data (Keenan, & Brockman,
2010, p.27). This means that it will not be possible to examine every single Mr. Big case that has
occurred for the case study design and analysis, thus limiting the scope of this study. This also
speaks to the notion that no two Mr. Big cases are the same, there are often similar tactics,
approaches, and target profiles when comparing Mr. Big cases, but there are differences in terms
of how investigations play out and the collection of evidence which can pose mild challenges in
drawing complete connections and conclusions from the relationships of various Mr. Big
Investigations. Outside of the content specifically, limitations can often be personal factors such
as age, experience, background, or even gender, but as a young woman who is aware of
privilege, discrimination, and biases that are present in society and law enforcement, the author
of this project must remain mindful in how the information is managed (Hoonaard, 2015, p.46).
When using content analysis, one must also be mindful of presentism when researching data and
studying cases due to changing laws and standards that occur over time (Hoonaard, 2015, p.68).
Lastly, a minor limitation of this study is that there are no recent statistics on Mr. Big police
operations and their usage in Canada. This is not an oversight of the RCMP as they are simply
unable to collect statistics on all their investigations, but this does place some limitation on the
exploration of the popularity or usage of Mr. Big operations in Canada.

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Defining and Explaining a Mr. Big Operation
Mr. Big is a Canadian undercover investigation technique developed by the Royal
Canadian Mounted Police (RCMP) in British Columbia in the early 1900s. The first Mr. Big case
in Canada was not all that successful, being referred to as “vile, base, and contemptible” by the
Crown due to questions around the admissibility of a confession (Keenan, & Brockman, 2010, p.
17). However, since then this investigative technique has become more advanced and has been
used widely by the RCMP, the most recent reliable statistics pertaining to the use of Mr. Big
operations can be found from 2008 from the RCMP reports that they had carried out 350 Mr. Big
sting operations in Canada with a 75% success rate; meaning the outcome of the investigation
resulted in obtaining a confession or that a suspect was cleared from the investigation
(Holmgren, 2017, p.159). Within this sample, the RCMP reported a 95% conviction rate when
able to gain a confession from the suspect that was admissible in court (Holmgren, 2017, p.159).
Although this is a positive statistic to reflect the use and the “success” of the operation in
Canada, it only addresses the outcome of using the technique, this does not provide a complete
assessment of the process in how a successful outcome is achieved. Mr. Big operations can be a
beneficial technique for law enforcement to rely on. However, due to creatively fashioned
interrogation techniques that allow for discretion within very nature of undercover investigations
they often have elements of coercion and deception in the pre-custody interrogations. There are
considerable questions around the operations credibility and reliability in obtaining confessions
that lead to “successful” convictions (Keenan, et al., 2010, p.17). Thus, opening the door for
criticism, critique, and a demand for oversight.
To provide background context, this is considered to be a last resort technique for cases
that have gone cold or where law enforcement strongly suspects someone of committing a crime

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but has been unable to obtain any effective physical evidence to file a charge (Milward, 2013,
p.81). This is a covert investigative technique because of the wide range of investigative
activities that fall under the umbrella of undercover investigations (Holmgren, 2017, p.154).
However, this technique differs from other kinds of undercover tactics because the officers
actually build an alternate environment by creating an entire ‘fake’ criminal organization
syndicate. Officers do this with the intent of building a relationship with the suspect to collect the
necessary confession and other incriminating evidence that is believed to be involved in the
crime under investigation. Evidence collected allows police to formally charge a suspect and put
them before the courts. According to Keenan and Brockman (2010), a Mr. Big scenario can be
explained as a number of undercover police officers who adopt fictitious criminal personas and
pose as crime figures, like gang members that are a part of a criminal organization in order to
deceive a target (suspect of said crime) into believing they are being initiated and conditioned to
join said criminal syndicate under the direction of the boss, Mr. Big. (Keenan, et al., 2010, p.19).
The investigation is essentially built on the premise of deceiving the suspect into believing he is
being conditioned to join this successful criminal organization in which his initiation into this
syndicate requires him to confess to his past crimes to “Mr. Big” (Holmgren, 2017, p. 152). It
has been said that the RCMP have perfected the backdrop that stimulates a “real-world criminal
environment” in which agents become swiftly intertwined directly and surreptitiously with the
criminal world projecting the fantasy making it nearly impossible for a target to differentiate to
reality (Keenan, et al., 2010, p.19).
The Process of a Mr. Big Operation
To further explain, Mr. Big police operations can be broken down into a 4-stage process
of intelligence probe, introduction, credibility-building and evidence gathering. During the

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intelligence probe police officers will conduct surveillance on the target to obtain information
about his friends, family, employment, lifestyle, hobbies, where free time is spent, routine, etc.
(Luther, & Snook, 2016, p.132). This prepares the officers for the next stage of introduction so
that they may tailor their approach, behaviours, and attitudes to best match those of the target
(Luther, & Snook, 2016, p.132). This will also help to prepare them for their interactions and
develop interactive scenarios prior to befriending the target (Keenan et al., 2010, p.19).
Researchers like Poloz (2015) emphasize the importance in this preparation as he suggests that
the fundamental success of a Mr. Big operation lies within the architecture of “establishing a
deliberate and disproportionate degree of psychological and emotional control over the accused”
(Luther, & Snook, 2016, p.232).
As for the introduction stage, an undercover officer will likely make contact with the
target while in police custody by the means of a third party or by attempting to recruit them
through their attendance at rehabilitation facilities, or their place of employment (Luther, &
Snook, 2016, p.132). The introduction consists of an undercover officer befriending the target
and introducing them to the fictitious criminal organization (Luther, & Snook, 2016, p.132).
After making contact with the target the officers will then engage in the credibility-building stage
by working to gain the targets trust through means of cash, sexual enticements, and
drugs/alcohol. The undercover operatives involve targets in fake criminal acts to give the
appearance of a real criminal syndicate; for instance, there could be physical assaults, drug
trafficking, mafia-style executions, picking up and dropping off parcels, counting large sums of
money, collecting unpaid debts, dealing with firearms, and the appearance of money laundering
all to demonstrate power and legitimacy (Puddister, & Riddell, 2012, p.386). This stage is crucial
to the success of the investigation as it is essential for the undercover officers to build a rapport

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and trust in this carefully structured relationship in order to be in a plausible position to obtain a
confession from the target (Keenan, et al., 2010, p.19). The undercover officers introduce the
suspect to this “gang lifestyle” over several weeks or months by involving them in minor crimes,
payment for criminal activities, and by displaying evidence of wealth (Smith Stinson, & Patry,
2009, p.170). This can be also be viewed as a bonding and grooming process as the officers take
the target on a range of crimes and activities from watching strippers, attending hockey games,
going to bars, discussing sexual exploits, and other various scenarios created by the officers to
establish ‘friendship’ and credit to the criminal enterprise this target is being recruited into
(Keenan, et al., 2010, p. 20).
Lastly, is the evidence gathering stage where the target it introduced to “Mr. Big” and the
officers work to obtain a confession and additional evidence that becomes crucial at trial in
convincing the suspect of the serious crime they are accused of. It is only once trust is solidified
that the target will be introduced to Mr. Big who will demand absolute truth and honesty from
the target about previous crimes (the offense in question) in order to establish credibility, loyalty
and to protect the criminal organization against future problems or surprises (Puddister, &
Riddell, 2012, p.386). Mr. Big is portrayed to the target as an all-powerful individual who has
connections in the criminal underworld as well as reliable police resources and other justice
officials in his pocket so that the target feels comfortable opening up (Keenan, et al., p.20).
The fictional crime boss works to get the confession during a covertly taped sit down
with the target and telling them that their honesty regarding the offense in question is mandatory
in order for them to be able to join the organization or for them to be helped by Mr. Big (Keenan,
et al., 2010, p.20) (Poloz, 2015, p.234). For example, Mr. Big could tell the target that he will
help him avoid criminal prosecution if he is honest about his involvement with the criminal

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investigation at hand. This stage puts pressure on undercover operatives to ethically follow the
legal guidelines established for them in how they should obtain a confession. Therefore, officers
must be extremely cautious in terms of “how they articulate the demands of honesty, trust,
dependability, and loyalty as requirements of the suspects membership” to the organization, as
the wrong moves can result in entrapment, coercion, false confessions and unreasonably
infringed rights of the target (Keenan, et al., 2010, p.20). It is due to these unique tactics Mr. Big
Operations call for guidelines and oversight to ensure due process and rights of a target are
upheld.
Criticisms of Mr. Big Operations
Since the early 1900’s, Mr. Big investigations have seen success, as Supreme Court of
Canada (SCC) Justice Moldaver said in the landmark R v Hart [2014] decision, the technique has
proven to be an effective investigative tool resulting in many convictions of cases that would
have likely gone unsolved, but the technique “comes with a price” (R v Hart, [2014] 2 SCR 544,
p.4-5). These investigations have become scrutinized and questioned for their tactics and ethics
as the target is expected to confess to Mr. Big during a non-custodial situation with often
“pointed interrogations and sometimes veiled threats” which leads to the rising speculation that
these investigations produce unreliable confessions (R v Hart, [2014] 2 SCR 544, p.5). Mr. Big
operations are often scrutinized due to their cost, secrecy (lack of public knowledge), the difficult
balance between police independence and oversight as these tactics demand un-biased officers
with capable discretion, and the fact there is an increased potential for false confessions and
wrongful convictions (Puddister & Riddell, 2012, p.385). As well as the ethical and legal issues
regarding the protection of the Charter of Rights and Freedoms section.7 and the right to silence,
s.11’s presumption of innocence, the applicability of the law in determining the voluntariness of
the confession, and if the tactics used are paramount to abuse of process or police trickery

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(Keenan, et al., 2013, p.67). Mr. Big operations have begun to raise three distinct concerns,
prejudice, reliability, and potential for police misconduct (Holmgren, 2017, p.155). The
questionable salient features being referred to are found in the implied threats of violence,
repeated confrontations with suspects with allegations of their guilt, false presentations of
evidence, and the untrue promise of “making the problem go away” (Milard, 2013, p.106).
These concerns address the reliability of information, the shadows of entrapment, and the
potential for coercion (Murphy, & Anderson, 2016, p. 30).
Although these tactics are considered necessary to deliver the alternate environment, this
technique neglects the protections of an in-custody interrogation and gives officers great power
to exercise discretion; leaving officers with the ability to freely apply confrontational tactics to
obtain a confession (Milard, 2013, p.110). Although, we see the RCMP claims a 75% success
rate with the Mr. Big investigative techniques, little is known about its “failures” (Smith, et al.,
2009, p.172). Speaking to the cases where the target was investigated but found innocent, was
wrongfully convicted, or had evidence ruled inadmissible (Smith, et al., 2009, p.172).
With that being said, some researchers hold the argument that the techniques of Mr. Big
operations are a serious intrusion into citizen privacy and create the breeding ground for false
confessions and unethical behavior to produce a guilty outcome (Milward, 2013, p.82). Thus,
pointing to the secrecy and the salient features within the operation that should require the
oversight and regulation by the SCC to scrutinize and assess the reliability of this technique
(Milward, 2013, p.82). Kouri Keenan, a consult and expert on Mr. Big investigative tactics,
explains that the details surrounding this technique are often shrouded in secrecy because the
success and nature of this investigation is dependent on the undercover work, revealing this
information would make this carefully developed technique essentially less effective (Holmgren,

18
2017, p.151). Although Mr. Keenan recognizes the classified nature of this undercover work
being essential to the technique’s success, he warns that the restricted access about how the
RCMP conduct these Mr. Big investigations can prevent oversight and public scrutiny; for the
presence of secrecy in any govern organization can create the opportunity for abuse of power and
ultimately threaten our Charter rights (Keenan et al., 2013, p.21). Therefore, one must consider
what errors fall and are hidden within this secrecy. This indirectly leads to another concern that
the legal system has difficulty balancing police independence in conducting their investigations
with the necessary accountability and oversight. Law enforcement must remain independent
without the government having too much control over police operations as this would disrupt
citizen’s independent bureaucracy and the legitimacy of policing.
The personal biases that law enforcement officers also carry can greatly influence the
process of the Mr. Big investigation and the interrogation. For instance, officers who hold a
“guilt presumptive” state of mind, meaning they believe and expect the suspect to be guilty, are
more likely to ask guilt presumptive questions, use more techniques to try to get the target to
confess, and often exert more pressure on suspects which often results in them becoming anxious
which displays itself as “suspicious behavior” (Smith, et al., 2009, p.181). This guilty
presumptive framework is especially worrisome as it can negatively influence the operations
success and infringe on the suspects s.11(d) Charter rights by not presuming them innocent until
proven otherwise in a court of law (Smith, et al., 2009, p.180). The operatives are also
scrutinized as it often appears that “when the courts impose restrictions on what police officers
can do in order to enhance reliability or protect the constitutional rights of the accused, the police
seem to find another procedure to bypass the rules” in order to obtain their evidence (Keenan et

19
al., 2013, p.32). The inability to be sure of officer bias and their ability to navigate oversight
creates room for criticism as a great deal of discretion is placed in the officer’s hands.
Another structural criticism of these operations lies in the financial burden and manpower that
Mr. Big operations require (Puddister, & Riddell, 2012, p.390). For example, one Mr. Big
operation alone may utilize as many as 50 police operatives and cost upwards of a million dollars
or more as they can extend from months to even a year (Luther, & Snook, 2016, p.133). This
places a great burden on law enforcement agencies and the justice system.
Producing False Confessions
Lastly, a vital criticism of Mr. Big operations is that they may produce false confessions,
often leading to wrongful convictions, this can happen through the salient means discussed
above. Past literature on wrongful convictions identifies police-induced false confessions as one
of the leading factors and causes for wrongful convictions today, with roughly 12% of
incarcerated criminals self-report that they falsely confessed to police (Smith, et al., 2009,
p.180). It is not all that uncommon for someone who is not guilty of a crime to plead guilty in
court once consulting counsel; therefore, it is not unreasonable to consider that innocent targets
in Mr. Big operations may confess to crimes they did not commit given the circumstances
(Keenan, 2013, p.32). For instance, the targets may overestimate their participation and
culpability in the crime in question and create stories of previous misdemeanors or add ‘details’
to portray themselves as worthy candidates to join the criminal organization or impress the crime
boss, Mr. Big (Keenan, 2013, p.47). They may also confess in order to escape the intense
situation with Mr. Big or to gain the perceived reward that Mr. Big is offering (Smith, et al.,
2009, p.180). After all, it is clear that the pressure on a target to confess in this evidence
gathering is substantial. It is evident through the examination of prior cases that the offers of

20
leniency or various benefits or gain, using threats of harm, or quid pro quos are casual links to
false confessions and thus wrongful convictions (Smith, et al., 2009, p.180).
This is not to mention that another crucial factor is the target’s age and mental capacity
(such as intellectually disadvantaged or mental illness). These two vulnerability factors can
increase the likelihood of suspects falsely confessing, in which these factors in combination with
Mr. Big tactics are more likely to produce false confessions from the target (Keenan, 2013, p.41).
In summary, Mr. Big operations often have elements that can lead to an individual to falsely
confess. Based on the very principle of the operation, a target may be seeking advantage,
acceptance, or street credibility, or the avoid negative consequences; all while being placed
under pressure unaware of the police presence. Which can lead to an individual to falsely
confess. Therefore, the circumstances of Mr. Big may be viewed as unethical as they undermine
the reliability of the confession and increase the chance of an innocent person confessing to a
crime they did not commit (Keenan, 2013, p.47).
Mr. Big Operations and Entrapment
In Canadian law, entrapment occurs when a government agent such as a law enforcement
officer induces someone to commit an illegal act that they would not have otherwise committed
(Smith, et al., 2009, p.179). Entrapment can be defined as the “conception and planning of an
offense by an officer, and his procurement of its commission by one who would not have
perpetrated it except for the trickery, persuasion, or fraud of officer” (R v Mack, [1988] 2 SCR
903, I. The Context). Entrapment can then be used as a criminal defense based on the interaction
between police officers and the defendant. In other words, this defense may be allowed in court
when someone has been “set up” or “trapped into committing a crime by police or police
informants (Barnhorst, & Barnhorst, 2013, p.87). The defense of entrapment would be a specific

21
application to the doctrine of abuse process. This would be the conviction of a person who had
been entrapped into committing an offense which brings the administration of justice into dispute
and would violate the values of the Charter and principles of fundamental justice (Stewart, 2012,
p. 268). This is often what people assume happens under the influence of an undercover
operation like Mr. Big.
R v Mack [1988]
The SCC case of R v Mack [1988] defined and discussed the issue of entrapment in great
detail. The SCC justices had to consider the specific threshold limits in which police misconduct
such as entrapment could be considered exceeding their reach of the permissible common law
limits (Keenan, 2013, p.36). As seen in other precedents the threshold to determine an abuse of
process by the police such as entrapment is quite high; with the complex variables at play in Mr.
Big investigations guidance and scrutiny is needed from the SCC to protect society (Puddister, &
Riddell, 2012, p.395).
Mr. Mack was charged with unlawful possession of narcotics for the purpose of
trafficking, but at the end of his trial his defense brought an application for a stay of proceedings
on the basis of entrapment (R v Mack, [1988] 2 SCR 903, The Facts). Mr. Mack said that the
individual who was a police undercover informer repeatedly asked to sell him drugs in person
and via phone calls. Mr. Mack refused to do so on multiple occasions until the undercover officer
threatened him and told him “to get his act together” when he did not provide the requested
drugs, he then eventually agreed to sell the narcotics (Barnhorst, & Barnhorst, 2013, p.87). The
appellant held that the police were not interrupting an ongoing criminal act but rather brought
about a conduct that wouldn’t have occurred without their involvement (R v Mack, [1988] 2 SCR
903, p.13). Therefore, the police were seen to be going further than merely providing an
opportunity to commit an offense (R v Mack, [1988] 2 SCR 903, p.13). The stay of proceedings

22
application at the first trial was refused and a conviction was entered, a notice of appeal was then
filed with the BC Court of Appeal, but it was dismissed. The case was appealed to the SCC who
allowed the appeal and officially determined that entrapment exists as a part of the abuse of
process doctrine (Barnhorst, & Barnhorst, 2013, p.87).
It is expected that police conduct is to be directed at obtaining evidence when an offense
is committed, but the tactics that involve questionable conduct that violate Charter rights cannot
be tolerated. In order to determine entrapment, there must be a critical distinction between the
police acting on a reasonable suspicion in the pursuit of a criminal investigation and providing
the suspect with the opportunity to commit a crime, and the state actually creating a crime for the
purpose of prosecuting said individual (R v Mack, [1988] 2 SCR 903, I. The Context). Canadian
Supreme Court Justice Willard Estey (as he was known then) explains that entrapment occurs
when the authorities (a) provide an opportunity to persons to commit an offence without
reasonable suspicion or, (b) have a reasonable suspicion and are acting in the course of a bona
fide inquiry but then go beyond merely providing an opportunity and induce the suspect into the
commission of an offense (R v Mack, [1988] 2 SCR 903, IV. The Proper Approach). Some
inducements that law enforcement include deceit, fraud, trickery, a reward, or calculated
inveigling and persistent importuning (R v Mack, [1988] 2 SCR 903, IV. The Proper Approach).
To determine whether the police have employed means which go beyond providing an
opportunity, the trial judge will consider factors such as the type of crime being investigated,
whether the average person in the position of the accused would be induced into the commission
of the crime, the accused’s resistance and number of attempts made by the police, type of
inducement, whether the police contact was exploitative, among other factors (R v Mack, [1988]
2 SCR 903, Summary). Therefore, if the trial judge decides there was entrapment from law

23
enforcement, it means the evidence obtained violated the Charter, thus bringing the
administration of justice in disrepute (R v Mack, [1988] 2 SCR 903, p.8).
In determining whether the doctrine of entrapment applies to the appeal of R v Mack
[1988], the SCC found that the police did entrap the suspect as it did not appear to be an
interruption of an ongoing criminal enterprise, the offense was clearly brought about by their
conduct, and they exploited Mr. Mack’s narcotic addiction (R v Mack, [1988] 2 SCR 903,
Summary).The appeal was allowed, and the conviction was set aside and entered a stay of
proceedings (R v Mack, [1988] 2 SCR 903, Summary).
Therefore, a target of a Mr. Big operation could be entrapped into producing a confession
when law enforcement officers overstep and induce a suspect rather than just providing an
opportunity. Law enforcement officers are given the right to investigate in which they are legally
and ethically allowed to use the Mr. Big technique, but if such tactics entrap a suspect to collect
evidence like a confession, it will likely be inadmissible as it violates the Charter and the
fundamental principles of justice. The decision of R v Mack [1988] is an important foundational
precedent that determines the threshold of entrapment so this principle can be applied to future
cases. This principle is further developed in more recent cases like R v Hart [2014].
R v Hart [2014]
In R. v. Hart [2014], the appellant was a father of two young twin daughters who
drowned in a lake adjacent to a park nearby their family home in 2002 (R v Hart, [2014] 2 SCR
544, p.17). Mr. Hart was immediately suspected to be responsible for their deaths but there was a
lack of evidence to charge him; two years following the drowning the RCMP began a Mr. Big
operation and recruited him into their fictitious criminal organization in order to collect evidence
(R v Hart, 2014, 2 SCR 544, p. 23). Four months into the investigation, Mr. Hart met Mr. Big

24
and confessed to killing his daughters, he was eventually charged with two counts of first-degree
murder and was convicted (R v Hart, 2014, 2 SCR 544, p. 35-37).
Mr. Hart appealed the conviction holding the operation was oppressive and led to a
breach of his fundamental rights under s.7of the Charter and that his confessions should be
inadmissible (R v Hart, [2014] 2 SCR 544, p. 40). Bringing attention to the admissibility of
confessions but also an entrapment defense as Mr. Hart was implying, he was exploited and led
into his ‘confession’. On appeal from the Newfoundland Court of Appeal, the SCC determined
whether a new common law rule of evidence should be developed to determine the admissibility
of Mr. Big confessions and if such confessions should be excluded. R v Hart [2014] is a
monumental case that changed the course of Mr. Big operations in Canada with the introduction
of a new common law confession rule for undercover operations.
The Interrogation Trilogy
The three cases of R v Oickle [2000], R v Singh [2007], R v Sinclair [2010] were heard by
the SCC and, in the Court’s rationale in the three cases, created the “interrogation trilogy” that
addresses different rules and rights under the common law and the Charter of Rights and
Freedoms. These precedents lay out safeguards for individuals in terms of limits on police
interrogation in obtaining confessions, the right to silence during interrogations, and the right to
counsel in context of police questioning (Dufraimont, 2011, p.309). The rationales from the
SCC in these decisions are critical in understanding the purposive principle of the Charter and
the protections it provides suspects, thus checking police conduct. The SCC emphasizes the
fundamental need for an appropriate balance of state interests and respecting entrenched
protections of the individual.

25
Confession Rule - R v Oickle [2000]
R v Oickle [2000] was an important case as it was the first comprehensive restatement the
SCC made of the ‘confessions rule’ since the Charter was established in 1982 (Smith, et al.,
2009, p.175). This case introduces the common law confession rule which outlines limits on
police interrogation, which also addresses some considerable concern around Mr. Big operations
producing false confessions (Dufraimont, 2011, p.309), (Keenan, 2010, p.33). The central issue
for appeal of Mr. Oickle’s conviction was the voluntariness of his confession, the defense
claimed that a number of factors in the interrogation raised reasonable doubts because the police
exaggerated the reliability of the polygraph, threatened his fiancé with a polygraph, and
minimized the legal significance of multiple convictions (Smith, et al., 2009, p. 175).
Furthermore, the justices were tasked with deciding whether the police improperly induced the
respondent’s confession through an environment of oppression, or through any threats or
promises, or tactics that would raise a reasonable doubt to the voluntariness of the confession (R
v Oickle, [2000] 2 SCR 3, p.1). In other words, the court was required to consider factors of
voluntariness in the use of police trickery, threats, or promises which set precedent to be applied
in multiple contexts such as Mr. Big operations (Smith, et al., 2009, p.175).
To briefly explain this case, between February 5th, 1994 and April 4, 1995, there were a
series of fires that appeared to be deliberately set involving buildings and motor vehicles, nearby
where Mr. Oickle and his fiancé lived, one fire which happened to consume his fiancés car (R v
Oickle, [2000] 2 SCR 3, p.4-5). The police conducted their investigation and narrowed their list
to seven or eight individuals to submit polygraph tests; most agreed to take the test or were
cleared, but Mr. Oickle was seen resistant and within a matter of minutes of the test being
administered it was determined he failed (R v Oickle, [2000] 2 SCR 3, para. 6-7). After being

26
reminded of his rights Mr. Oickle then confessed to setting fire to his fiancée’s car, within the
next four hours he would also confess to setting seven to eight fires (R v Oickle, [2000] 2 SCR 3,
p.9).
At the initial trial, the judge held a voir dire to determine the admissibility of the
accused’s statements and ruled they were admissible and voluntary; Mr. Oickle was then
convicted on all counts (R v Oickle, [2000] 2 SCR 3, p.10). However, Mr. Oickle’s charges were
appealed to the Nova Scotia Court of Appeal and they overturned the conviction, excluded the
confessions from evidence, and an acquittal was entered. This was after considering the
respondent was
(N)ot coherent and in control during the videotaped interrogation, he was not aware
the role of the equipment, while the police were minimizing the seriousness of the
offense and did not clarify the polygraph results were not admissible as evidence which
breached the respondent’s trust by unfairly and aggressively exploiting the results of the
tests as a confession inducing instrument (R v Oickle, [2000] 2 SCR 3, p.10-18).
The SCC allowed the appeal on the basis that the statements in question were the only
evidence that directly implicated the respondent and without establishing their admissibility there
would be no reasonable trier of fact to convict Mr. Oickle which was needed to convict without a
reasonable doubt (R v Oickle, [2000] 2 SCR 3, p.21). This highlighted the importance in
protecting the Charter which upholds fundamental rights of due process and the value in ensuring
innocent people are not convicted (Smith, et al., 2009, p.175). Justice Iacobucci (as he was
known then) wrote the majority rationale for the decision and identified that the Charter is not an
exhaustive catalogue of rights for one to follow. He stated there is the utmost importance for the
confessional rule to be administered on the principle of protecting the rights of the accused, but

27
without unduly limiting society’s need to investigate and solve crimes (R v Oickle [2000] 2 SCR
3, p.31, p.33) (Keenan, 2010, p.34). Justice Iacobucci (as he was known then) also addresses the
value of the confession rule in its ability to help with understanding problems surrounding false
confessions and how it will uphold the diversity in confession approaches taken by law
enforcement. (R v Oickle, [2000] 2 SCR 3, p.32).
The SCC majority decision outlined that confessions must be identified as voluntary to be
reliable, because an involuntary confession will be likely unreliable and thus inadmissible. This
distinction is important as the confessions rule does not explicitly exclude statements elicited by
undercover officers; statements could often be interpreted as involuntary due to the undercover
nature of the interrogation and various and “can still violate the Charter” but that would become
a matter for the courts to decide, any statements is not automatically involuntary or inadmissible
(R v Oickle, [2000] 2 SCR 3, p.28). The confession rule can be explained as, out of court
statements made by an accused to a person of authority (law enforcement) are admissible as
evidence, but only when statements can be without a reasonable doubt deemed voluntary in
nature. For instance, “statements made as the result of intimidating questions, or questioning
which is oppressive and calculated to overcome the freedom of will of the suspect for the
purpose of extracting a confession” could become involuntary (R v Oickle, [2000] 2 SCR 3,
p.33). This is not to neglect the operating mind of a suspect when confessing as this is important
to consider alongside other elements of voluntariness (Dufraimont, 2011, p.312). To further
explain, interrogation tactics that subtly minimize moral and legal consequences of a conviction
by discrete suggestions about the benefits of confessing to an offense are deemed useful to
police. These are not considered unreasonable or shock worthy to the community; but only as
long as these tactics do not raise questions as to the voluntariness of the accused’s confession

28
(Smith, et al., 2009, p.176). In which police interrogations are subjected to limits of the SCC
decisions of the interrogation trilogy like the confession rule, right to counsel and right to silence
(Acheneftos, 2010, para.2).
Certain interrogation tactics such as Mr. Oickle being misled by having the reliability of
evidence in the accuracy of polygraph exaggerated to him by police alone does not invalidate a
confession, rather the manner in which conducted could challenge admissibility and the
voluntariness (R v Oickle, [2000] 2 SCR 3, p.95). However, some tactics with greater threat like
deception that fall under “police trickery” as seen in investigative tactics of Mr. Big operations,
the common law requires a separate inquiry into the police trickery, meaning tactics must be held
to a standard that would not “shock the community’s conscience” (Dufraimont, 2011, p.312).
Not only would the voluntariness of a statement then need to be decided but it would also need to
be held to a standard of shock worthy to the community.
The SCC found that Mr. Oickle was not offered any inducements strong enough to raise a
reasonable doubt to the voluntariness of the confession where there was no mistreatment and a
mildly oppressive environment (R v Oickle, [2000] 2 SCR 3, p.104). The SCC then moved to
restore the trial judge’s conviction of Mr. Oickle and set aside the Court of Appeal’s judgment.
Therefore, Mr. Oickle’s were considered voluntary given the circumstances and could be
admissible and used as evidence to convict him of his guilt. To interpret this confession rule in
the circumstances of a Mr. Big operation where police trickery is often used, it is beneficial to
identify that there is a standard of voluntary and involuntary confessions in which they must be
obtained in a manner that would not “shock the community”, meaning interrogation tactics must
not go beyond a reasonable level of inducement, oppression, or mistreatment in order to mitigate
false confessions or confessions obtained at the expense of the accused’s rights.

29
In conclusion, the circumstances surrounding the voluntariness of a confession depend on
the use of presence of threats or promises, oppression, and the operating mind; this also includes
the consideration of police trickery that would “shock the community” to obtain a confession.
Right to Silence - R v Hebert [1990] and R v Singh [2007]
As the Charter does not explicitly state a “right to silence”, the SCC played a critical role
in shaping limitations on interrogation practices as they recognize Charter s. 7 principles of
fundamental justice are constitutionally protected (Dufraimont, 2011, p.313).
R v Hebert [1990]
The recognition that an accused’s right to silence is protected by s. 7 of the Charter is
derived from the precedent of R v Hebert [1990], which first addressed s.7 in terms of pre-trial
right to silence. This was a foundational decision for focusing on whether a statement made by a
detained person to an undercover officer would violate the Charter; based upon the critical
importance of achieving a balance between societal interests and the interests of the individual’s
rights (R v Singh, [2007] 3 SCR 405, p.45). Supreme Court Justice McLachlin (as she was
known then) narrowly defined the right to silence in the rationale as, “the right to choose freely
whether or not to speak to authorities” (Dufraimont, 2011, p.313). Therefore, in scope of the
confession rule, jurisprudence on confessions revealed a theme linking the exercise of one’s free
will in choosing to speak to ensure the impugned statement would not result in bringing the
administration of justice into dispute (R v Singh, [2007] 3 SCR 405, p.34). In the Hebert case, the
appellant (Hebert) refused to speak with police but was tricked into making incriminating
statements to an undercover officer in the same jail cell. The Court found that the police
effectively negated Mr. Hebert’s free will in his choice to remain silent thus violating his rights.
The particular circumstance in undercover investigations where the individual is not aware they

30
are speaking to an authority the court outlined specific facts to support a suspect who is not yet
detained (R v Singh, [2007] 3 SCR 405, p.46).
To further explain, the Hebert decision established the fact that officers who are not
undercover, in which an accused chooses on their own will to volunteer information, there is no
violation of the charter. Furthermore, police persuasion, “short of denying the suspect the right to
choose or depriving them of an operating mind” will also not breach the right to silence (R v
Hebert, [1990] 2 SCR 151, D. Conclusion). Although, there are different facts and considerations
for undercover operations where officers are able to obtain information from the suspect prior to
the detention. The Court explains this is because an undercover operative is technically not in
control of the state and there is no need to protect a suspect from the “greater power of the state”
in such instances (R. v. Hebert, [1990] 2 SCR 151, D. Conclusion). In other words, the
undercover operative is not detaining the individual but rather investigating, in which the Court
found this section 7 protection would only apply after the suspect is detained by law enforcement
(Puddister & Riddell, 2012, p.394). Justice McLachlin then emphasizes a distinction between
undercover agents to observe a suspect and the use of undercover agents to elicit information in
violation of the suspects choice to remain silent (R. v. Hebert, [1990] 2 SCR 151, D.
Conclusion). For example, as Mr. Big operations are a way of obtaining information or evidence
from the target prior to detention, police may often use tactics such as deceit to interrogate the
target after he or she has advised the police that they do not want to speak any further. The police
would then likely be considered breaching the suspects rights by improperly eliciting information
they were unable to obtain when initially respecting the suspects right to silence, thus taking
away the suspects choice (R v Hebert, [1990] 2 SCR 151, D. Conclusion). Regardless, Mr. Big

31
stings do not require protection from the state because the technique is considered an
investigative function not a process of detaining the suspect (Puddister, & Riddell, 2012, p.394).
R v. Singh [2007]
More recently, the SCC in R v Singh [2007] had to readdress and consider the concept of
self-incrimination from which the confession rule and right to silence are derived. There was
considerable overlap between the inquiry into voluntariness of the statement and the review of
s.7 in the alleged breach of the right to silence (R v Singh, [2007] 3 SCR 405, p.24). To provide
a brief case summary for context in explaining this decision, Mr. Singh was arrested for second
degree murder of a bystander outside a pub who was killed by a stray bullet. There was no
forensic evidence, but a doorman of the pub was able to identify Mr. Singh as the shooter in a
photo lineup (R v Singh, [2007] 3 SCR 405, p.11). Mr. Singh was told of his right to counsel
under s.10 and did consult with counsel (R v Singh, [2007] 3 SCR 405, p.2). In two police
interviews, Mr. Singh made it known he did not want to talk about the incident or knew anything
about it. He asserted his right to silence 18 different times in these interrogations, officers would
affirm his right but would continue to engage (R v Singh, [2007] 3 SCR 405, p.13). By the end of
the interrogation, Mr. Singh did make incriminating statements as he admitted to being in the
pub on the day of the shooting and identified himself in the photograph, and then identified
himself as a man in a videotape taken outside the pub on the night of the shooting (R v Singh,
[2007] 3 SCR 405, p.12).
During the voir dire to determine the admissibility of these statements prior to the trial,
the judge followed the precedent of the confession rule from R v Oickle [2000], where he
rationalized, he was “satisfied beyond a reasonable doubt that the statements were voluntary”
and admitted the evidence based upon its probative value (R v Singh, [2007] 3 SCR 405, p.3).

32
Mr. Singh was convicted at trial and appealed to the British Columbia Court of Appeal on
grounds of his s.7 right, arguing that if there was a proper application of s.7 the police would
have had to of stopped trying to obtain admissions (R v Singh, [2007] 3 SCR 405, p.17). The
Court of Appeal dismissed the appeal and concluded that the way in which the trial judge relied
on the precedent of R v Hebert [1990], in terms of s.7 protection, the police persuasion in this
interrogation did not deny Mr. Singh of the right to choose, nor did it deprive him of an operating
mind; therefore, Mr. Singh’s s.7 right was not infringed, making the evidence admissible (R v
Singh, [2007] 3 SCR 405, p.18). The SCC, in a 5-4 majority decision, dismissed Mr. Singh’s
appeal for conviction as the statements made in a police interrogation room were found to be
made voluntarily, meaning they were obtained in a manner that did not infringe Mr. Singh’s
rights and his conviction was upheld (Dufraimont, 2011, p.314).
The majority decision explains that in the context of a police interrogation of a person in
detention, “there are two tests for determining whether the suspect’s right to silence was
respected” and are functionally equivalent (R v Singh, [2007] 3 SCR 405, p.25). One test
assesses the voluntariness of a confession under s.7 by using an objective test to assess the
exercise of the accused’s free will (R v Singh, [2007] 3 SCR 405, p.36). The second test follows
the same directives of the confession rule (R v Singh, [2007] 3 SCR 405, p.36). However, Justice
Charron (as he was known then) who wrote the decision notes that these tests are only
functionally equivalent when the “the confession rule effectively subsumes the constitutional
right to silence,” meaning this test only applies in circumstances where the person is obviously in
detention and is being interrogated by a known authority (R v Singh, [2007] 3 SCR 405, p.39).
As mentioned, R v Oickle [2000], this means that the confession rule will only apply when the
suspect is aware that they are making a statement to a person in authority. Furthermore, the

33
jurisprudence relating to the right to silence has never, and currently does not extend to the
protection against police tricks or any pre-detention interrogations (R v Singh, [2007] 3 SCR 405,
p.46). Police persuasion or any conduct considered just short of denying the suspect their right to
choose or depriving their operating mind does not breach the right to silence only once the
accused is detained (R v Singh, [2007] 3 SCR 405, p.46). Therefore, an undercover agent who is
unknown to the accused does not fall into this category and as R v Hebert [1990] and R v Singh
[2007], have established the target in such operations really has limited protection of s.7 in their
right to silence until detained.
The notion of voluntariness in the right to remain silent speaks to the principle that a
person is not obliged to talk, answer, or give information to police, in which an individual is
unaware of the authority they unintendedly waive a ‘volunteering’ of a statement (R v Singh,
[2007] 3 SCR 405, p.31). In the consideration of the confession rule, police trickery that would
deny an accused’s right to silence could then be considered to produce an involuntary statement,
and if found to reach the standard that shocks the community it is likely to be ruled inadmissible
as it is an unreliably obtained statement (R v Singh, [2007] 3 SCR 405, p.35). Therefore, further
emphasizing that in Mr. Big Operations officers engaging in police trickery may overstep and
deny the accused their right to silence through oppressive environments with Mr. Big and the use
of threats or promises that influence his or her operating mind making any statements
involuntary. However, to assess the voluntariness of a confession under s.7, Justice Charron
explains that focus is directed to the conflict of police and the effect on the suspects ability to
exercise their free will (R v Singh, [2007] 3 SCR 405, p.36).
Mr. Singh’s appeal was based on an issue that the police did not respect his constitutional
right to remain silent. However, the SCC’s majority decided that under this two-step functional

34
equivalent test of the confession rule the statements were found voluntary, and the fact Mr. Singh
had free will but chose to continue to speak to officers after asserting his rights makes these
statements admissible evidence (R v Singh, [2007] 3 SCR 405, p.49). The dissenting justices,
however, held an interesting alternative in disagreement of the majority decision, explaining they
believe that the ability of the police to investigate crime in Canada would be not be impaired by
effective exercise to pre-trial right to silence as implied by rational of Justice Charron (R v Singh,
[2007] 3 SCR 405, p.82). Holding that a detainee’s right to silence should rather be respected
and not deliberately undermined by police through their persistence (Dufraimont, 2011, p.315).
Right to Counsel – R v Sinclair [2010]
R v Sinclair [2010] is the third and final case to explore in the interrogation trilogy. In
this case, the SCC considered the meaning of s.10, and the various implementation duties of
police in custodial interrogations (Dufraimont, 2011, p.315). Chief Justice McLachlin and Justice
Charron wrote the majority decision explaining that the appeal concerns the nature and limits of
the right to counsel under s.10 of the Charter, concerning statements made during interrogations.
Section. 10(b) of the Charter is to allow a person who has been arrested or detained the “right to
retain and instruct counsel without delay and to be informed of that right” which places
informational and implementation duties on the police which they must inform the detainee and
also provide the opportunity and ability to exercise that right (Dufraimont, 2011, p.315). The
issue for Mr. Sinclair was whether he, as a detainee in police custody, had properly been
accorded his s.10 Charter right to further consultations with counsel during the course of
interrogations (R v Sinclair, [2010] 2 SCR 310, p.1).
Mr. Sinclair was charged with second degree murder for killing another man but was
convicted at trial for manslaughter (R v Sinclair, [2010] 2 SCR 310, p.4). The conduct in

35
question concerns the interrogation of Mr. Sinclair after his arrest. Mr. Sinclair was said to be
advised he was being arrested and was read his Charter warning of the right to retain and instruct
counsel without delay, and that a legal aid lawyer would be available free of charge (R v Sinclair,
[2010] 2 SCR 310, p.5). He did not want to contact a lawyer right away and was taken to the
RCMP detachment where he was asked if he wanted to exercise his right. Mr. Sinclair did speak
to his lawyer by the phone in a private room for three minutes (R v Sinclair, [2010] 2 SCR 310,
p.6). Later in the day, Mr. Sinclair’s interrogation lasted for around 5 hours and he upheld his
right to silence. As questioning continued to progress, Mr. Sinclair repeatedly expressed
discomfort within being interviewed without his lawyer. Four- or five-times Mr. Sinclair
adamantly expressed a desire to speak with his lawyer and his intent to remain silent without his
guidance (R v Sinclair, [2010] 2 SCR 310, p.10). However, each time he asked the interrogator
validated Mr. Sinclair’s right but continued to proceed with further questioning and tactics of
confrontation to get Mr. Sinclair to confess (Dufraimont, 2011, p.316). The RCMP explained
that Mr. Sinclair’s right to counsel was considered satisfied through the prior telephone call and
he was not entitled to have his lawyer present during the questioning. By end of day, the police
had placed Mr. Sinclair in a cell with an undercover officer in which he made an incriminating
statement and then accompanied the police to where the murder occurred and participated in a
re-enactment (R v Sinclair, [2010] 2 SCR 310, p.13).
At trial, a voir dire was conducted to determine the admissibility of the statements Mr.
Sinclair made during the initial interview, the exchange with the undercover officer and the reenactment (R v Sinclair, [2010] 2 SCR 310, p.15). It was proven that the statements were
voluntary and admissible in court. The trial judge further decided that s.10 of the Charter had
been satisfied with the phone call with his lawyer prior to the interview (R v Sinclair, [2010] 2

36
SCR 310, p.15). The defense appealed the conviction of manslaughter specifying the appellant’s
repeated requests to speak with his lawyer during the course of the interview that were denied
constituted a breach of s.10 (R v Sinclair, [2010’ 2 SCR 310, p.16). The British Columbia Court
of Appeal dismissed Mr. Sinclair’s appeal and affirmed his conviction. The case is then brought
to the SCC where Mr. Sinclair continued to argue that s.10 requires the police to respect a
detainee’s request to have counsel present during a custodial interrogation (R v Sinclair, [2010] 2
SCR 310, p.18). The SCC dismissed the appeal in a majority decision of 5-4, finding Mr.
Sinclair’s s. 10 right was not unreasonably breached.
Mr. Sinclair had argued that the wording of s.10 makes it clear this right arises upon
detention but there is no text to directly indicate when the right is exhausted or satisfied, The
Court had to consider if “retain and instruct” implies a continuing right, or if “on arrest or
detention” indicates a specific point in time and not a continuum (R v Sinclair, [2010] 2 SCR
310, p. 20-21). This required the SCC to conduct a purposive analysis of s.10 of the Charter,
where the Court determined the purpose of this right is to provide the detainee with an
opportunity to obtain legal advice relevant to the legal situation (R v Sinclair, [2010] 2 SCR 310,
p. 24). As identified in R v Hebert [1990], s.7 and s.10 work together to ensure a suspect is able
to make the choice to speak to investigators in which they can exercise their operating mind
through free will and informed decisions (R v Sinclair, [2010] 2 SCR 310, p. 25). The SCC then
made a crucial distinction specifying that the state is not obliged to protect the suspect against
making incriminating statements, but rather obliged to use legitimate means of persuasion to
encourage a suspect to do so and allow the suspect to make informed choices (R v Sinclair,
[2010] 2 SCR 310, p. 26).

37
In further analysis of s.10, Chief Justice McLachlin and Justice Charron analyze the
purpose and continuance of the right. The SCC decided that the right to counsel that arises upon
detention is satisfied by law enforcement doing two things: offering an initial warning where the
detainee is informed of their right to counsel and affording reasonable opportunity for the
detainee to consult the counsel (Dufraimont, 2011, p.316) (R v Sinclair, [2010] 2 SCR 310, p.
27). This was demonstrated by law enforcement notifying Mr. Sinclair of his s.10 right and
providing him two opportunities to reach a lawyer and allowed him to speak to said lawyer.
However, Sinclair advanced that a detainee should have a lawyer present upon request during the
entirety of the interview and that this right should be a continuous ‘protection’ (R v Sinclair,
[2010] 2 SCR 310, p. 33). The Court explained that s.10 does not contemplate such a
requirement, as the wording in the Charter “reasonably connote more than a perfunctory
consultation prior to the interrogation” (R v Sinclair, [2010] 2 SCR 310, p. 35). Thus, there is no
implied notion that counsel should be present throughout the interview process. There is also the
notion that changing circumstances would allow the detainee to consult their counsel a second
time. In a matter of a “change in jeopardy”, meaning the investigation takes a more serious turn
the initial advice from the lawyer may no longer suit the situation (R v Sinclair, [2010] 2 SCR
310, p. 51). Therefore, the Court decides that the detainee must be given further opportunity to
consult with counsel to obtain advice on the new situation to fulfil the purpose of s.10 (R v
Sinclair, [2010] 2 SCR 310, p. 51).
Section 10 of the Charter should be interpreted in a way that fully respects the purpose of
supporting the detainees s.7 right to silence (R v Sinclair, [2010] 2 SCR 310, p. 47). The Charter
intersects as s.10 and s.7 often overlap. For instance, if an accused’s s.10 right to counsel is
denied, their statement will likely be involuntary, thus inadmissible as evidence in consideration

38
of s.7 and the confession rule. Furthermore, if the police comply with s.10, it will not make a
statement automatically voluntary. If a voluntary statement is made by the accused, there could
still be a breach of s.10 (R v Sinclair, [2010] 2 SCR 310, p.29). The question outlined in this case
concerned whether Mr. Sinclair should have been given a second opportunity to consult with a
lawyer when asked. The majority decided that Mr. Sinclair did not satisfy any of the categories
that would satisfy re-consultation with his counsel. Hence, he received his legal advice fulfilling
the purpose of s.10 as there was no change in jeopardy he was facing (R v Sinclair, [2010] 2 SCR
310, p.66). In conclusion, this case set precedent that outlined the proper performance functions
of s.10, further identifying the critical balance between individual rights and the intentions of the
state.
Canadian Charter of Rights and Freedoms Implications
To understand an accused’s rights during police investigations, the purposive elements of
the Charter must be explained. The Charter is a critical document that lays out the rights and
freedoms Canadian’s believe are necessary in a democratic and free society (Government of
Canada, 2020, para.1). The Charter identifies and enshrines six broad categories of rights
consisting of: fundamental freedoms, democratic rights, mobility rights, legal rights, the right to
equality and equal benefit under the law, and language rights (Sharpe & Roach, 2017, p.48-49).
The Charter’s rights and freedoms radiate its foundational values that are used to protect
individuals and the social contract in Canada; values of equality, human dignity, autonomy,
religious freedom, fairness, expressive freedom, advancement of democracy, and privacy are
upheld through various sections (Sharpe, & Roach, 2017, p.54-57). The Charter of Rights and
Freedoms is entrenched in the Canadian Constitution making it supreme in law with its rights

39
and freedoms to Canadian’s. Therefore, it is protected and highest of all other laws, meaning all
other statues must be consistent with the Charter.
The boundaries, purposes, and definition of the sections of the Charter have developed
over time from Supreme Court precedent, which has transformed the course of criminal
investigations and the judicial proceedings while expanding legal rights in terms of the accused.
The Court must interpret and apply the meaning of the Charter to protect the core principles and
values of equality, human dignity, fairness, autonomy, expression freedom, religious freedom,
democracy advancement, and privacy. Overtime the Charter has been able to increase the
judicial responsibility and the ability delineate the line between crime control and due process
(Sharpe, & Roach, 2017, p. 295). In exploring the legal rights that are engaged by criminal
investigations such as Mr. Big operations it is important to understand that the Charter is a
purposive document that is interpreted and explained based upon the Court’s purposive method
of interpreting the meaning of the right or freedom with the issue at hand to determine whether
the matter consists of an infringement (Sharpe, & Roach, 2017, p.56).
However, the rights and freedoms provided by the Charter are also not absolute, as
identified by s.1 there can be justifiable ‘reasonable’ limits to where the interests of society at
large or the rights of other individual will justifiably require limitations (Sharpe, & Roach, 2017,
p. 53). Section 1 guarantees the rights and freedoms but defines they are subject to “limitations
prescribed by law” in which the sections are subject to “reasonable limits” when they can be
demonstrably justified in a free and democratic society (The Constitution Act, 1982, Schedule B
to the Canada Act 1982 (UK), 982, c11, s.1). To determine what is reasonable in terms of
infringement section 1 imposes the Oakes test, derived from R. v. Oakes [1986], in which this

40
decision made it clear, judges must proportionally review the case using the discretion of
minimal impairment (Sharpe, & Roach, 2017, p. 81).
The Oakes test is a two-step process: the first step asks if the legislative goal is pressing
and substantial, speaking to the state’s objective being important enough to justify the limitation.
The second step asks if there is proportionality between the objective and the means used to the
state’s objective (Department of Justice, 2021, para. 3. The Oakes Test). If a judge answers yes to
the above questions, they must then consider three different branches of (a) rational connection,
the limit being rationally connected to the objective, (b) minimal impairment, asking if the
challenged legislation infringes on the right or freedom more than what is necessarily for the
legislation’s objective, and (c) the final balancing, that there must be proportionality between the
effects of the law (Department of Justice, 2021, para. 3. The Oakes Test). Although, section 1
“does not play a role in police officer’s actions in limiting the Charter right are not specifically
authorized or prescribed by law” (Sharpe, & Roach, 2017, p. 67). In other words, if the conduct
of law enforcement violates, but is not authorized by statute or is not set out in the law, it cannot
be justified under section 1. In such situations, a court would go straight to a remedy phase of
the analysis (Sharpe, & Roach, 2017, p. 67).
The Charter essentially provides legal safeguards to protect the right of the defendant and
to try to minimize errors of the investigation process; in which section 7 of fundamental
freedoms and section 11, pertaining to proceedings in criminal and penal matters are most often
engaged in this regard (Smith, et al., 2009, p.173). The Supreme Court of Canada’s role in
setting precedent that determine the parameters of police powers has expanded greatly since the
introduction of the Charter of Rights of Freedoms in 1982; leading the SCC to hear arguments
questioning Mr. Big cases that infringe section 7 rights (right to silence), the admissibility of

41
statements, persons in authority doctrine, and the abuse of process and dirty tricks (Puddister, &
Riddell, 2012, p. 393).
Section 7 of the Charter: Fundamental Justice
Section 7 of the Charter of Rights and Freedoms states, “everyone has the right to life,
liberty and security of the person and the right not to be deprived thereof except in accordance
with the principles of fundamental justice” (Canadian Charter of Rights and Freedoms, Part I of
the Constitution Act, 1982, being Schedule B to the Canada Act 1982 (U.K.), 1982, c11 s 7).
This right is seen upholding many Charter values as it engages personal liberty. To further
explain, courts have determined the concept of “fundamental rights” and the scope of their
protections in applying section 7. As the Charter holds a purposive approach, this section of the
Charter addresses the concern between proper balance of individual rights and the proceedings of
an accused’s life, liberty or security (R v Herbert, [1990] 2 SCR 151, III. Purpose of Right to
Silence). Section 7 is an essential legal right as it seeks to impose limits on the power of the state
over a detained person (R v Singh, [2007] 3 SCR 405, p.45). It provides protection against the
unfair use of the state’s superior resources but also maintains the state’s power to deprive a
person of their life, liberty, or security in which balance of right is crucial to the administration
of justice.
To begin understanding section 7, the language of this right such as concepts of life,
liberty, and security of the person must briefly be defined. The right to life would be used in
instances where the state conduct would deprive an individual of their life (Stewart, 2012, p.63).
This is to say the SCC has recognized “life” in a civil sense and in consideration when
someone’s survival is at stake. They have not yet addressed the scope of life directly; although it
is engaged when there is a substantial risk to life. Liberty is more complex with its various legal

42
and political discourses, but liberty allows individuals to be free from physical constraint. When
there are deprivations of liberty by state actions like inhibiting an individual from making
choices on personal decisions without interference their section 7 right would be engaged
(Stewart, 2012, p.65). This means that an average citizen is free from state-imposed unjustified
constraint or imprisonment because they cannot be deprived of their liberty; hence people’s
liberty is only restricted once they have been given a fair trial and are guilty beyond reasonable
doubt as this is a fundamental principle.
The SCC has identified that in the interest of liberty it is not merely restricted to mean
physical restraint either, but in instances where the state compulsions or prohibitions affect the
importance of fundamental life choices (Stewart, 2012, p.68). This aspect of liberty is engaged in
penal proceedings, civil proceedings, prison conditions, parole eligibility, psychiatric detention,
among others. This ensures that section 7 is meant to protect against any state-imposed
deprivation of one’s liberty that does not comply with principles of fundamental justice (Stewart,
2012, p.71). Lastly, security of the person refers to both bodily and psychological integrity of the
individual. It has been interpreted by the SCC that state imposed “psychological stress” is a
component of the criminal law context (Sharpe, & Roach, 2017, p.252). Therefore, security of
the person includes and exceeds physical integrity of the person, property and immediate
surroundings of a person, and their psychological integrity. These foundational concepts of life,
liberty, and security will be engaged when the state interferes in profoundly intimate and
personal choices of the individual (Sharpe, & Roach, 2017, p.252).
Through continuous SCC decisions the principles of fundamental justice are constantly
evolving, growing, and being redefined. Since section 7 is the foundation of the legal rights the
fundamental freedoms it upholds are necessary in advancing this discussion. The aspects of

43
fundamental principles connect with individual personal choices and privacy interests, in which
there are three main categories in which the SCC has defined a range of principles: fault,
procedural and substantive. The “fault principles” refers to mens rea, the act of the crime relating
to the individual’s criminal intent. As well as including aspects of procedural fairness (justice)
that serve to protect the administration of justice and substantive justice principles that protect
the individual from unjust laws (Stewart, 2012, p.126). To further explain, substantive principles
of fundamental justice are most often associated with the areas of statues, regulations, and
common law rules. Thus, principles of fundamental justice under a substantive lens require laws
not to be overly vague, not to be overly broad, nor arbitrary, or not grossly disproportionate and
must uphold moral blameworthiness (Stewart, 2012, p.127-149). With that being said there are
numerous principles to govern the penal aspects of the law including investigations. This
introduces the need for procedural justice which covers a wide range of fundamental principles
that the SCC has deemed crucial such as: the right to full disclosure, best evidence rule, the right
to full answer and defense, as well as the presumption of innocence and the right to silence. All
of which are seen as interacting principles in the context of Mr. Big operations.
Although section 7 provides an individual procedural right under the general language of
section 7, they are not specifically guaranteed as specifically laid out in legal rights of sections 8
to 14 but through these internal principles are upheld (Sharpe, & Roach, 2017, p.303). This is to
mention that this section of fundamental justice is different from other Charter sections as they
are not a free-standing guarantee. A critical distinction that these rights are only invoked where
state action or law has violated life, liberty, and security of the person, (Sharpe, & Roach, 2017,
p.255). Furthermore, the SCC has recognized this point through the “residual role” section 7
plays in relation to the other specific guarantees in s.8 through s.14. This section is a

44
“steppingstone” for other protections, serving as a foundation of all conduct that fundamental
justice principles must be respected and upheld (Stewart, 2012, p.9).
Procedural Fundamental Justice Principles: Right to Silence
Section 7 and the right to silence applies when a detainee is speaking to an agent of the
state (Stewart, 2012, p.211). In penal investigations, section 7 protects the procedural principles
of fundamental justice that a detainee has the right to silence and thus should make an ‘informed’
decision about whether to speak to an authority (Stewart, 2012, p.210). The SCC has
demonstrated, as written by then Justice McLachlin, that the right to silence of a detained person
must be broad enough to grant a detained person a free choice on whether to speak or remain
quite (R v Herbert, [1990] 2 SCR 151, I. Related Rights). This is notwithstanding the fact that he
or she is in the superior power of the state. (R v Herbert, [1990] 2 SCR 151, III. Purpose of Right
to Silence). This fundamental principle affords that a person who is not detained, rather a
suspect in an investigation retains the protection of general liberty under section 7 in which they
are to decide whether or not to speak to an officer (Stewart, 2012, p.210). As established through
the confession rule a statement must be deemed voluntary for it to be admissible, in which an
individual is protected from prejudice, inducement, oppressive questioning, or other police
misconduct or trickery as the right to remain silent is a principle of fundamental justice and
engaging in such behavior to obtain confessional evidence would be a section 7 infringement of
the suspects liberty and right to silence (Stewart, 2012, p.212).
To further explain, the right to silence by its nature is exercised differently than the other
legal Charter rights. For example, the Charter’s section 8 right to counsel is held within the
control of an accused with an operating mind in which conduct from the authorities does not
impact the detainee by taking away his or her ability to choose (R v Singh, 2007, 3 SCR 405,

45
p.43). This means in an undercover officer scenario where a “fellow inmate” is sharing a cell in
which a confession is spoken it is not always considered an infringement of section 7 in how it
was obtained. As explained in R v Singh and R v Hebert, the common law recognizes an
individual’s right to remain silent, but this does not mean that authorities cannot speak to this
individual, there is constitutional importance in law enforcement being able to perform their
investigative duties. The SCC has identified that the scope of this right to silence for individual
to exercise must also extend to exclude tricks which would effectively deprive the suspect of this
choice, this means authorities cannot trick the suspect into making a confession after they have
exercised their right (R v Hebert, [1990] 2 SCR 151, III. Purpose of Right to Silence).
In the case where police trickery is in question, the SCC held that two questions must be
asked, “was the evidence obtained by the state?” and “was the evidence elicited?” only if the
answer is yes to both of these will there be a section 7 violation. This is not to say that this
protects an individual from being questioned, or that the police are not allowed to continue
questioning the suspect once they have reasserted their right to silence or once they have
obtained counsel (Stewart, 2012, p.212). It is only where police questioning or trickery denies
the suspect of the right to choose or deprives them of an operating mind that police questioning
can violate the right to silence (Stewart, 2012, p.212). As the Charter does not explicitly
guarantee a right to silence, this principle of fundamental justice must continue to be outlined in
consideration of the evolving cases. Although the recognized pre-trial right to silence afforded
under section 7 also leads to section 11(c) of the Charter that protects against the principle of
self-incrimination; both of these rights prevent the Crown from arguing that an individual
selecting to invoke their right to silence would imply or be evidence guilt (Stewart, 2012, p.247).

46
Violation of Section 7.
Section 7 is considered infringed if there is a deprivation of life, liberty, or security of the person
or if there is deprivation of the principles of justice (Department of Justice, 2019, para. 4).
Therefore, in face of a section 7 Charter violation (section 7 test) the applicant must demonstrate
that (1) there is some state conduct to which the Charter applies, meaning is there a practice,
policy, law, or lawful exercise of state authority that infringes on the individuals life, liberty or
security, (2) the applicant is a ‘natural persons’, (3) the state conduct affects the applications life,
liberty, security of the person and (4) the conduct is not in accordance to those afforded
principles of fundamental justice (Stewart, 2012, pp. 21-22). This burden of proof for the
analysis of section 7 puts the burden on the applicant to demonstrate that their right to life,
liberty, or security of the person had been denied against the indefinable principles of
fundamental justice in which it must meet the civil standard on the balance of probabilities
(Sharpe, & Roach, 2017, p.254). State conduct that will be assessed refers to the areas of statutes
and regulations, government entities, private and public law litigation, as well as the exercises of
statutory powers and discretion among the various state conduct surrounding investigations. In
summary, an applicant must be able to demonstrate that their section 7 right was violated on the
basis of the discussed fundamental principles.
Justification under Section 1.
If the three elements required of a violation are established it is still “theoretically”
possible for such act to be rescued by section 1 where the government could be justified but
these cases will be extremely rare (Sharpe, & Roach, 2017, p.88 & pp.246-247). The SCC has
specified that a violation of the Charter s.7 will only be saved by s.1 in cases arising out of
“exceptional conditions like natural disasters, the outbreak of war, and epidemics, and the like”
(Sharpe, & Roach, 2017, p.247). The strict definition of section 7 places limitations on

47
determining violations where the influences of section 1 analysis to determine an infringement of
the right is not required (Sharpe, & Roach, 2017, p. 88). To further explain, section 7 is different
at its core as it holds internal qualifiers where the requirement of the state to respect the
“principles of fundamental justice” will overlap with the section 1 test for justification of a
reasonable infringement, in which it is very difficult to justify a violation under section 1
(Stewart, 2012, p.5).
A section 7 violation holds a significant burden of proof, which if met would demonstrate
that such conduct was not in accordance with the principles of fundamental justice that could
rarely be justified under section 1 of the Charter as it violated the individuals very right to life,
liberty, and security (Stewart, 2012, p.289). Justice Wilson furthers this rationale by saying, he
does “not believe that a limit on s.7… could either be reasonable or demonstrably justified in a
free and democratic society” (Stewart, 2012, p.289). This identifies the utmost value and respect
for the principles of fundamental justice on their own, for only in extreme cases should an
individual’s section 7 right ever be justifiably infringed. Otherwise, section 7 and the principles
of fundamental justice are so critical they cannot be overridden or infringed on the basis of state
or social interests (Stewart, 2012, p.290). Therefore, the section 1 justifications for violations
under section 7 are considered “rare” as they simply would not be able to pass the minimal
impairment aspect of the Oakes test due to the utmost importance of the fundamental principles
of justice (Sharpe, & Roach, 2017, p.89). The threshold for justifiably in limiting section 7 rights
is a higher threshold than the one used in s.1 for limiting other charter rights as it requires
extreme circumstantial situations to even consider a “reasonable” justification for such violation
(Stewart, 2012, p. 290).

48
Section 11(d) of the Charter: Innocent Until Proven Guilty
Section 11 of the Charter identifies the legal rights afforded to an individual who is
charged with an offense. It highlights procedural justice foundations that lay out principles and
rights while placing limitations on judicial proceedings within the subsections a through i. This
section only applies to criminal or quasi-criminal proceedings, and proceedings that give rise to
penal consequences, meaning it applies to the prosecutions for criminal offences (Sharpe, &
Roach, 2017, p.325). Section.11(d) will be of particular focus as it states the right to be presumed
innocent until proven guilty according to law in a fair and public hearing by an independent and
impartial tribunal (Canadian Charter of Rights and Freedoms, Part I of the Constitution Act,
1982, being Schedule B to the Canada Act 1982 (U.K.), 1982, c11 s 11). The presumption of
innocence itself is an essential principle in Canada’s free and democratic society in which it is
committed to values of fairness and social justice (Sharpe, & Roach, 2017, p.330). The rights
protected under section 11 are residual, pertaining to upholding all the principles of fundamental
justice, and the life, liberty, and security of the person as identified in section 7 (Canadian
Charter of Rights and Freedoms, Part I of the Constitution Act, 1982, being Schedule B to the
Canada Act 1982 (U.K.), 1982, c11 s 11).
With that being said, in light of undercover Mr. Big operations and confessions, section
11(d) is critical to understand in securing an accused’s liberty. Section 11(c) is another important
residual right. It also protects an individuals’ right against self-incrimination, but it only relates
specifically to the event of the trial of an accused and protects them from not having to testify in
court that would incriminate them. This right is not of value to the discussion of Charter right
engagement and Mr. Big (Sharpe, & Roach, 2017, p.328). With that being said, the purpose of
section 11(d) ensures that those who are guilty are ultimately condemned by the justice system,

49
but also ensures the guilt is determined in a fair process of reasonable doubt, upholding the
essential foundational values of the Charter such as, fairness and life, liberty and security
(Department of Justice, 2021a, Purpose). This brings attention to the presumption of innocence,
the very principle the Canadian criminal justice system operates on, the principle that people are
presumed innocent until they are proven, beyond a reasonable doubt to the satisfaction of judge
or jury that they are guilty of the offense being tried; meaning everyone is innocent until they are
convicted in court of law (Sharpe, & Roach, 2017, p.469).
The presumption of innocence is a basic fundamental right in the Charter. Its specifically
aims to restrain coercive power which helps avoid the risk of wrongful conviction and it also
upholds the due process of the justice system to those who are ‘guilty’ (Sharpe, & Roach, 2017,
p.295). The term “innocent” is defined as “wrongly accused of having committed all the
elements of the offense” or including they have no true defense to their charge (p.13). Section 11
is protected under the legal rights and is built upon the foundation. of section 7 but they do vary
in terms of their applicability. For instance, for s.11 infringements it becomes the crown’s
responsibility to determine that the proved fact does not flow from the presumed fact in which
11(d) would be limited and requires to be justified under the section 1 Oakes test (Department of
Justice, 2021a, Section 1 Considerations).
This can be a difficult right to understand as an accused must rely on their defense in
which they are subjected with the legal burden of proving their innocence; but yet the right is
supposed to allow them to be presumed innocent (Mahoney, 1988, p.14). Regardless of how
complex, the SCC has ruled that an accused relying on a defense is not necessarily asserting
innocence, in which it reaches outside the sphere of a Charter guarantee of the presumption of
innocence (Mahoney, 1988, p.14). The presumption of innocence then becomes a more moral

50
aspect of the Charter than legal, but it is crucial to uphold until the accused is proven guilty
(Mahoney, 1988, p. 18).
In order to justify a section 11 infringement, it would be subjected to s.1 Oakes Test, in
which the individual would need to rebut the presumption and the crown would need to establish
the standard of minimal impairment in which the absence of the presumption would mean the
offence cannot operate effectively (Department of Justice, 2021a, Section 1 Considerations).
This interpretation can be applied to regulatory offences and judicial independence outside of the
presumed facts facing an accused. However, the SCC has demonstrated that under section 1, the
accused must be able to use a balance of probabilities for their defense of due diligence or lack of
negligence which can be challenging (Sharpe, & Roach, 2017, p.332). Furthermore, the vital role
played by judicial independence in the constitution and the charter values has also been
demonstrated by the SCC that the standard application of section 1 test could not alone justify a
reasonable infringement of an individual’s independence (Department of Justice, 2021a, Section
1 Considerations). Section 11 also holds some structure of internal tests, in which only in the
direst circumstances could a government present convincing evidence to justify an infringement
on someone’s judicial independence. The SCC continues to interpret the presumption of
innocence in a broad sense so that regardless of the existence of a reasonable doubt as to guilt,
the individual’s right could still be infringed whenever a person may be convicted (Sharpe, &
Roach, 2017, p. 332).
R. v. Hart [2014]
The R v Hart [2014] case is the most recent SCC landmark case where a two-pronged
framework for assessing the admissibility of Mr. Big confessions was created. This case brought
attention to interaction of the Charter and the confessions rule, in light of a complex undercover

51
technique. As mentioned in earlier discussion, Mr. Hart was a father of two young twin
daughters who drowned at a park under his supervision in 2002 (R v Hart, [2014] 2 SCR 544,
p.17). Three-year old Karen and Krista Hart went with their father to a neighbourhood park to
play, which also had a lake adjacent to it (R v Hart, [2014] 2 SCR 544, p.16). Mr. Hart and the
girls were gone for roughly 30-45 minutes until he returned home without his daughters, telling
his wife that Krista had fallen into the water and he had forgotten Karen at the park (R v Hart,
[2014] 2 SCR 544, p. 17). Moments later Mr. Hart and his wife were back at the park with an
ambulance where Krista and Karen were found floating several meters apart from each other,
they were pronounced dead (R v Hart, [2014] 2 SCR 544, p. 18).
Mr. Hart was immediately suspected to be responsible for their deaths due to his “unusual
behavior” (R v Hart, [2014] 2 SCR 544, p. 19). It was suspicious that he did not call anyone or
stop anywhere closer for help, yet he denied any accusations that he had drowned the girls (R v
Hart, [2014] 2 SCR 544, p.19). However, there was very little information available with no
witnesses and no other evidence beyond Hart’s statements (Murphy, & Anderson, 2016, p.30).
Two weeks following the initial questioning, Mr. Hart volunteered that he had not been truthful
in his previous statements, saying he had a medical seizure at the park and when he “came to”
his daughters were laying in the water. Although, the police were convinced he was guilty but
there was a lack of evidence to charge him, and the case went cold.
Two years following the drownings, the RCMP began a Mr. Big operation targeting Mr.
Hart in order to collect evidence for the case. The officers began their surveillance in December
2004 and made their first move to recruit him into their fictitious criminal organization by
February 2005 (R v Hart, [2014] 2 SCR 544, p. 23). Mr. Hart was unemployed, receiving social
assistance, was antisocial and was a rather socially isolated person; thus, it was not a challenge

52
for the undercover officers to weave themselves into his life and get him to participate in
numerous simulated criminal activities with the officers while he received financial rewards and
travelled around Canada. By April 2005, Mr. Hart was hooked and admitted he felt he had
“brothers” within this friendship he had built with the operatives (R v Hart, [2014] 2 SCR 544,
p.26-28,38). By May 2005, the operatives began working towards Mr. Hart meeting Mr. Big,
they told him that there was a “big deal” coming in that would “set [Mr. Hart] up financially” but
only if he was approved to participate in the deal by Mr. Big who recognized a past criminal
problem and needed to meet with him to resolve it (R v Hart, [2014] 2 SCR 544, p. 32).
When Mr. Hart met Mr. Big, he was asked about the death of his daughters and why he
had killed them, Mr. Hart admitted he had suffered a seizure in which their deaths were an
accident, but he denied killing them (R v Hart, [2014] 2 SCR 544, p. 34). Mr. Big pushed further,
using various interrogation tactics such as reassuring the respondent not to “lie”, prodding in the
events further, along with having the incentive of monetary gain and legal assistance; by the end
of the meeting Mr. Hart confessed to drowning his daughters (Hunt, & Rankin, 2014, p.323). He
rationalized that he killed the girls out of fear that he would lose them to the province’s child
welfare agency, he said the girls “fell” over the dock, but when pressing further he also revealed
he had “struck his daughters” (R v Hart, [2014] 2 SCR 544, p.35-36). Two days after this
confession Mr. Hart went to the location of the crime and re-enacted how the droning occurred,
Mr. Hart was then shortly charged with two counts of first-degree murder for the death of his two
daughters, Krista and Karen. In total there were three confessions made from Mr. Hart during
this investigation.
Mr. Hart was convicted at trial level and then appealed his conviction holding the
operation was oppressive and led to a breach of his fundamental rights under section 7of the

53
Charter, and that his confessions should then be inadmissible (R v Hart, [2014] 2 SCR 544, p.
40). This forced the judges to consider the admissibility of confessions and his defense of
entrapment as Mr. Hart was arguing that he was exploited and was led into his ‘confession’. His
appeal to the Newfoundland Court of Appeal was dismissed as the appeal court did not feel Mr.
Hart was threatened and had the operating mind to leave at his will throughout the operation (R v
Hart. [2014] 2 SCR 544, p.41). When appealed again, the SCC had to address if the confessions
made by Mr. Hart during the Mr. Big operation should be admissible, and if it breached his
section 7 right to silence.
As seen in the interrogation trilogy, the SCC in the past held that Mr. Big undercover
operations simply do not engage the right to silence because the accused is not detained by the
police at the time in which they confessed. Further, the confession rule requires a confession to
be ‘voluntary’ it becomes an inoperative standard because the accused is not aware they are
talking to an authority or in the presence of the state when they confess (R v Hart, [2014] 2 SCR
544, p. 64). This can alternatively be viewed that the accused does not have an operating mind to
leave because they are not yet detained and thus do not know they are confessing to an authority.
Mr. Big confessions could be challenged through the abuse of process doctrine or upon the
discretion of a judge to determine is probative value; however, infringed challenged Mr. Big
confessions is not a common finding in the common law (R v Hart, [2014] 2 SCR 544, p. 65).
Furthermore, the SCC found that the threshold in which this previously described framework
protects the rights of the individual was inadequate in protecting them in Mr. Big investigations.
They agreed that Mr. Big confessions do present unique dangers that must be addressed “by
placing a filter on their admissibility”; the past law provided insufficient protection to an accused

54
due to the danger of unreliable confessions, the prejudicial effect of Mr. Big confessions and the
risk of police misconduct (R v Hart, [2014] 2 SCR 544, p.66).
The New Common Law Rule
In his decision on behalf of the Court, Supreme Court Justice Moldaver brought attention
to the fact there is considerable danger in confessions obtained by Mr. Big in terms of reliability.
As the very purpose of the operation is to induce a confession, there is risk in the various tactics
used on the pretense that a suspect will confess about the crime being investigated because they
are under the impression such confession could result in a consequence free escape and allow
them to join an organization and all its appealing rewards (R v Hart, [2014] 2 SCR 544, p. 68).
Another concern was that there are considerable prejudicial facts present when dealing with the
accused’s character in court of law. This means the jury may negatively interpret that the target
as a person because he or she was willing or wanted to join a criminal organization and
participated in crime they thought believed was real; this could unintentionally convey bad
character of the accused (R v Hart, [2014] 2 SCR 544, p. 73). Furthermore, the SCC advanced
that Mr. Big confessional evidence that is unreliable and prejudicial presented before the jury
would invite miscarriages of justice. Lastly, limiting police misconduct is of large concern due to
the nature of the operation. These investigations create a risk that an officer may resort to
unacceptable or unethical tactics in obtaining the confession as they are working under pressure,
with an alternative identity, in an environment of violence and stress which can perpetuate
threats or violence resulting in the police going “too far” in their investigation of the suspect (R v
Hart, [2014] 2 SCR 544, p. 78).
The confession rule or the right to silence did not address the uniqueness of Mr. Big
operations and did not afford an accused of all their legal rights under the Charter in these

55
situations which puts them at a disadvantage (R v Hart, [2014] 2 SCR 544, p. 79). The SCC
decided that there was not an effective mechanism for monitoring police conduct when
undercover and that there needed to be a ‘better’ law to protect individuals. To remedy this the
Court outlined a new common law rule for Mr. Big investigations. Created with the intention of
balancing the dangers posed by Mr. Big operations while ensuring police have the tools they
need to investigate, Justice Moldaver outlined a new common law rule to determine the
admissibility of Mr. Big confessions and if such confessions should be excluded in court. (R. v
Hart, [2014] 2 SCR 544, p. 84).
This rule is a two-pronged approach that recognizes a new common law rule of evidence
and relies on a more robust conception of the doctrine of abuse process to address reliability,
prejudice, and to address police misconduct (R v Hart, [2014] 2 SCR 544, p. 119). The new rule
determined that confessions obtained in the course of Mr. Big operations are to be presumptively
inadmissible. They can be admitted but the Crown must establish on a balance of probability that
the probative value of the confessions should outweigh its prejudicial effect (Hunt, & Rankin,
2014, p.322). This approach is consistent with the demands of self-incrimination and other
Charter legal rights that uphold protecting against abusive state conduct and unreliable
confessions (R v Hart, [2014] 2 SCR 544, p.123). The first prong of the test to determine
reliability of the confession in Mr. Big operations concerns the probative value, in which the
circumstances surrounding a confession need to be assessed whether they would influence the
reliability of the confession made (R v Hart, [2014] 2 SCR 544, p.132). Factors that are now
considered by judges include the number of interactions between the target and police, the nature
of the relationship between undercover operatives and target, the extent and nature of the
inducements presented to the target, if there were any threats, the interrogation itself, and the

56
personality and mental characteristics of the target such as their age, mental disorders,
sophistication, etc. (Hunt, & Rankin, 2014, p.325). The prejudicial effect of the matter refers to
the prejudice that could result based on the targets desire to join the organization or their
participation in the simulated crimes that could dampen his other character in the fair trial (Hunt,
& Rankin, 2014, p.322).
In the second prong of the new evidentiary test, Moldaver acknowledged the abuse of
process doctrine had provided little protection for the accused in Mr. Big investigations because
it would be nearly impossible to determine a threshold for when such operation could become
abusive, especially given its secretive properties (Hunt, & Rankin, 2014, p.325). The SCC then
suggested that signs of abusive practice within the context of these operations included behavior
such as threated or actual physical violence, psychological coercion that overcomes the will of
the accused, or operations preying or targeting on vulnerabilities such a substance abuse,
youthfulness, mental health issues, etc. which would be highly problematic for the confession to
be reliable in this context (Hunt, & Rankin, 2014, p.325) (Murphy, & Anderson, 2016, p.38).
Regarding the admissibility of Mr. Hart’s confession itself, the SCC considered that he
had confessed on three separate occasions but the justices also considered those crucial factors
that he was isolated, unemployed, and living on welfare, in which the operation had
“transformed” his life for the better; he was heavily involved in scenarios and had daily contact
with these officers during the course of the investigation making this a “lengthy and intense
operation” (R v Hart, [2014] 2 SCR 544, p.133). Mr. Hart was also exposed to powerful
inducements, Mr. Big claimed he could offer Mr. Hart a financial gain that would bring him out
of poverty if he was admitted into this organization, in which the respondent would want to tell
the crime boss what he wanted to hear. The circumstances at play left Mr. Hart with the choice of

57
confessing to Mr. Big or be deemed an untrusting liar by the very organization he wanted to join
(R v Hart, [2014] 2 SCR 544, p. 140).
Given all these circumstances in light of the new rule and the overwhelming incentive to
confess, with the lack of consistency and confirmatory evidence the Court found the reliability of
Mr. Hart’s confessions in serious doubt in which the probative value of them was low (R v Hart,
[2014] 2 SCR 544, p. 144). In such situations, the crown would likely be unable to demonstrate
the confession to be admissible, resulting in the remaining evidence surrounding the Mr. Big
operation becoming irrelevant and thus inadmissible (Murphy & Anderson, 2016, p.38). Mr.
Hart’s confession should be excluded and ruled inadmissible, the justices also did not focus on
the police misconduct specifically because they do not think the conduct amounted to an abuse
of process; however, they acknowledge that behavior such as preying on the respondent’s status
of poverty, his social isolation, and his poor health put the respondent a risk and warranted
excluding the confessions (R v Hart, [2014] 2 SCR 544, p. 148). This SCC decision allowed for
multiple factors to be considered within this new two-pronged test that supports the rights and
freedoms of the accused, while adapting to the unique circumstances of these undercover
operations.
Legal Implications and Discussion
The Mr. Big investigation is incredibly interesting for its complexity and use by Canadian
police since the 1990s with claims of effectiveness for solving cold and unsolved cases (R v
Hart, [2014] 2 SCR 544, p.56). This investigative technique is not used without criticism due to
the secretive nature of this undercover operation and that police discretion is heavily relied on.
Misconduct is often an issue at the forefront of these investigations as prejudice, unethical
tactics, and the intrusion of an accused’s Charter rights may easily occur in such settings. The

58
concerns and criticisms of Mr. Big operations are crucial to examine and discuss as such
instances can create Charter infringements of the accused’s rights. Principles of reliability and
prejudice are fundamentally evidentiary issues. Canada being a free and democratic society with
a constitutionally enshrined Charter must uphold the values and principles of fundamental
justice.
It cannot be denied that the Mr. Big technique has been beneficial to the Canadian justice
system in collecting evidence and leading to solving many cases that would have otherwise gone
cold. The search for truth is paramount to police investigations but the procedures being used
must also be conducted in a manner that properly operates within the context of legislation and
constitutional authorities, such as protecting the Canadian Charter of Rights and Freedoms in
respect to the ‘target’ (Poloz, 2015, p.235).
There is a foundational need on the basis of the principles of justice for the courts to
strive for an appropriate balance between crime control and the protection of society.
Nonetheless, courts must also focus on the balance of providing fairness to the accused persons
and preventing abuse of police powers on the other (Sharpe, & Roach, 2017, p.295).
Involuntary or False Confessions
There are significant ethical and legal issues raised by Mr. Big operations. These concern
the right to silence, applicability of law on the voluntariness of confessions, deciding if the
tactics used during the investigation are tantamount to an abuse of process, if the admission from
the accused is considered reliable, and the risk of a false confession (Keenan, 2010, p.65). To
further explain, psychological science has also made it clear that in planning and conducting law
enforcement interrogations, such as those conducted by Mr. Big in the final evidence gather
stage, interviewers must be cognizant of and concerned about the risk of an accused’s memory
distortion, possibility of a false confession and accurately interpreting the ‘deception’ (Porter, et

59
al., 2016, p.36). These characteristics could present themselves, become heightened, or be
misinterpreted by officers given the context of the unique undercover operations. The occurrence
of these risks could result in many involuntary confessions which would likely create unreliable
evidence, if these issues commonly arise during these investigations, it reasonably could damage
the effectiveness and legality of the operation.
Undeniably, it is an advantageous opportunity in undercover policing for a probable
suspect to be unaware that they are speaking to an officer or informant. This covert tactic has
been proven to be reasonable; similar to probing, open ended questions, and other interrogation
approaches. Although the argument with Mr. Big operations does not lie in the secretive or
undercover nature but rather the influence of officer conduct, enticements, and the overall
complete alteration of reality that may unfairly disadvantage the individual. As it is, ‘targets’ of
Mr. Big operations are different at a foundational legal level as they miss out on many of the
protections and familiarity that a standard custodial interrogation offers.
Accusatory Interview Style
To further explain the impact of interrogation style, using Canadian police interrogation
transcripts, it has been shown that there is a clear presence of an accusatory interview style used
among the RCMP and other Canadian police agencies. Research shows that fewer than 1% of the
questions asked to a suspect during interrogations were open-ended, where 40% and 30% of the
police questions asked were shown to be yes/no and probing questions (Porter, et al., 2016,
p.37). Such questions even in “normal” interrogation settings demonstrate the police take
advantage of tactics that could ultimately impact the truthfulness and the effectiveness of the
evidence (Porter, et al., 2016, p.37). Canadian police will do so with accusatory strategies and
approaches in which they confront the target with direct accusations, continuous probing, or
verbal threats. This more aggressive approach is possible through the lack of oversight and

60
potentially poor officer discretion that could go beyond a reasonable threshold of tactics,
subjecting the accused to unreasonable treatment or foster unreliable evidence.
Aura of Violence
The success of a Mr. Big operation often depends on the very environment and
relationship to which the undercover operatives expose the target. This means that the
investigation is perceived to create an aura of violence deliberately cultivated to reinforce the
supposed organization’s values of honesty, trust, and loyalty (R v Hart, [2014] 2 SCR 544, p.
59). These values can function as an inducement to confess as they are critically important to Mr.
Big and impact the accused’s future “membership”. This aura can be seen through the simulated
acts of violence that the operatives may involve the target in. These violent acts can influence a
target’s perception of the situation and the reliability of their confession. For instance, many
targets may confess in order to brag or impress Mr. Big, in doing so, they are seeking acceptance
in which they may falsify the information presented (Sukkau, & Brockman, 2015, 70). However,
the issue is not so black and white, police report that creating a coercive atmosphere during
interviews has been useful in collecting information from a suspect as some pressure is necessary
(Acheneftos, 2010, para.2). Loosely built off the principle of “bad cop, good cop”, the goal of an
interviewee should be to approach the interview in such a way that the suspect would willingly
volunteer a confession. This requires the police to balance the interests of their interrogation
while protecting the individual from unreasonable intrusion. This is often easier said than done
as evident in appeals to the SCC and the evolution of common law in addressing these unique
interrogations (Acheneftos, 2010, para.6). For not only can the environment of non-custodial
interrogations and the aura of violence impact an accused’s behavior and potentially reliability of
their confession, but the tactics specifically used by operatives during the interrogation can

61
borderline an unreasonable degree of police trickery or engage the abuse of process doctrine in
which directly engage the Charter of Rights and Freedoms.
Inducements for a False Confession
In the addressing the possibility of false confessions under the operation of Mr. Big the
possible suspect would become a “coerced-compliant”; an innocent individual who confesses “in
exchange for a promised incentive, or to escape mistreatment by law enforcement all why
knowing [they are] innocent (Porter, et al., 2016, p.37). The promises of legal protection,
monetary gains, friendship, a scapegoat, job, etc. that Mr. Big offers to the target could be
interpreted as considerable incentives for an individual to confess. The potential for a false
confession to occur can increase in proportion to the nature and the extent of the inducements
being held out to the target (R v Hart, [2014] 2 SCR 544, p. 69). The danger of a false confession
during a Mr. Big interview can pose a greater risk than custodial interrogations because of their
emphasis on costs and benefits being significantly misrepresented to the suspect as their entire
environment is altered (Hunt, & Rankin, 2014, p.328). Furthermore, the target may even be told
that Mr. Big has “conclusive evidence of their guilt”. Denying the offense would just prove to
Mr. Big that they lack trustworthiness and thus cannot join the organization they desperately
want to be a member (R v Hart, [2014] 2 SCR 544, p. 60). This puts a different type of pressure
on the accused to produce a statement.
Psychological Stress
The significant role of the intimidating environment perpetuated by Mr. Big during the
meeting and the tactics employed during could make the suspect feel an unreasonable amount of
psychological or physical stress. This calculated addition of stress in these circumstances begins
to threaten the target’s right to security. As Keenan (2010) explains, self-incriminating
statements alone are induced when life changing promises of wealth, professional advancement,

62
and the avoidance of penal sanction are being held, they may even mis portray themselves to
show that they are a worthy candidate to Mr. Big (p.47). It is in these circumstances that one can
begin to question if the investigation would undermine the reliability and value of the evidence,
and potentially create further unnecessary risk of wrongful convictions.
Police Officer Discretion
In light of the significant role police discretion plays in conducting these investigations, it
is conceivable that officers may struggle with bias toward labelling suspects as guilty and
deceptive simply based on demeanor, behaviour, or questionable evidence, rather than remaining
objective. The SCC recognized the “moral prejudice in these circumstances [to be] significant (R
v Hart, [2014] 2 SCR 544, p.145). Given the extensive work and information building required
from the undercover operatives, there is a greater sense of pressure on maintaining the
presumption of the target’s innocence (Smith, et al., 2009, p.181). However, if police are also
investigating with the belief that the suspect is guilty of the offense, the balance of the interests
between securing evidence for a conviction and the target’s legal rights may become a blurred
line (Smith, et al., 2009, p.181). One of the largest criticisms of this technique is officers who
hold a guilty-presumptive frame of mind which can negatively influence the operation and
infringe the suspects s.11(d) Charter rights by not presuming them innocent until proven guilty in
a court of law. With that being said, section 7 of the Charter is also engaged and is necessary to
consider in determining if the target has a right to silence as protected by the common law and
the Charter in these investigations.
Engagement of the Charter of Rights and Freedoms
The Charter’s section 7 principles against self-incrimination and the rule of law are two
fundamental organizing values of the Charter that are relevant to Mr. Big investigations (Keenan
et al., 2010, p.32). Section 7 of the Charter established the legal protections that are afforded to

63
everyone are intended to put reasonable limits on police conduct. In Mr. Big operations, a section
7 infringement can occur as a result of the officers depriving the target of their right to life,
liberty, and security. This can happen through coercing confessions, entrapment, or using unjust
tactics that do not respect the right to silence. This potential infringing behavior or tactics
alongside the principles of section 7 of the Charter have been discussed at length earlier. It is also
crucial to understand the moment in which these protections are engaged in Mr. Big operations
to fully understand the influence the Charter has on Mr. Big operations in its role to ensure a fair
and reliable investigation to ensure a fair administration of justice.
As seen in the confession rule, the right to silence applies any time a person interacts with
a person of authority regardless of if they are detained or not. This allows an individual to
exercise their personal freedom in choosing the extent to which they cooperate with police. The
SCC has furthered this principle through new common law which established a recognition of
the potential for coercive impacts from state authorities and the risk of individuals incriminating
themselves (Keenan, 2010, p.65). As identified in section 7, the principle of moral
blameworthiness requires evidence of the accused before holding them criminally responsible as
this can lead to wrongful convictions (Barnhorst, & Barnhorst, 2013, p.48). This ability to
produce evidence of moral blameworthiness in Mr. Big operations is a complex task in which the
law enforcement methods could bring about inaccurate, coerced, or unreasonable evidence which
brings the effectiveness and the ethics of this approach into question.
Furthermore, these Mr. Big operations do not usually have control over a target’s
movements. Depriving the target of their section 7 right to silence could occur by law
enforcement by engaging in the various SCC explained abusive practices and behaviors that
intrude on the individual’s ability to exercise their operating mind (Sharpe, & Roach, 2017,

64
p.107). Such illegal tactics can threaten the liberty and security of the person and would not
uphold the principles of fundamental justice, rendering any confessional evidence collected to be
subjected a test of admissibility. To make a confession admissible when it does not pass the
section 7 test would bring the principles of fundamental justice into disrepute. With that being
said, under the new common law rule developed by the SCC, confessions obtained in the course
of Mr. Big operations are to be presumptively inadmissible due to the very nature of the
investigation and the risks associated. This is not to say the confessions cannot be admitted, but
the Crown must establish using a balance of probability that the probative value of the
confessions should outweigh its prejudicial effect.
This approach supports the section 11 right that emphasizes the plausibility of an accused
to make a self-incriminating statement to an undercover officer. Some researchers argue that
these statements should be excluded entirely because they were admissions made simply as a
result of the circumstances of implied threats, psychological manipulation, and/or significant
inducements held out by what the accused would have perceived as a person of authority in this
criminal syndicate.
The alteration of reality unconsciously shapes the accused’s behavior and perception,
creating an opportunity for law enforcement officers to engage but also fosters unreliability due
to ‘set up’. These Mr. Big operations place a type of psychological control on the target as they
are socialized into a life of crime and degradation which can become a powerful force in
inducing false confessions and controlling the individual (Keenan, 2010, p.68). Undercover
operatives are considered bypassing a suspect’s right to silence when they persistently continue
talking to the suspect, or if a confession is coerced. The right to silence would become infringed
when police operatives go astray from the directed control and tactics that are deemed within

65
reason. Canadian’s value and live in a free and democratic society where anyone is free to
remain silent in the face of police questioning and should not feel compelled or left with no other
choice but to confess (Keenan, 2010, p.32). In circumstances where the target is unaware of the
authority or that they are undergoing a form of police questioning, the values and principles of
section 7 must be upheld to protect the accused against self-incrimination or making a false
confession.
Section 11 and the presumption of innocence is a requirement in law to be fair and
interacts with the idea that Mr. Big operations target a suspect based on a suspicion of guilt. In
the pursuit of a confession where law enforcement believes the target is guilty, there is
opportunity for bias, pressure, and prejudices to interfere which can negatively impact state
discretion in which s.11(d) could be violated in their pursuit of a confession. This can possibly
happen as law enforcement may dismiss that the person is innocent until proven guilty beyond a
reasonable doubt in court. This can happen because the police feel that the evidence, their
intuition or other factors lead to different conclusions (Department of Justice, 2019, para. 4).
Officers have both a common law and statutory duty to investigate crime and should be given all
the necessary skills and tools to be able to uphold that duty. Nonetheless, they are not provided
special authority above the law. They may reasonably exercise any authority given to them by
the state. However, an officer is relied on to exercise their own discretion in exercising their
authority. It is in this discretional conduct that the Charter applies to and where infringements
can easily occur (Stewart, 2012, p.37). If law enforcement strictly follows methods of
intelligence-gathering or ‘truth-seeking agenda’ that is taught and enforced by trained
psychologists, they would intuitively advise against using any physical or extreme psychological
coercion that we see commonly occurring in Mr. Big operations (Porter, Rose, & Dilley, 2016,

66
p.36). Thus, police should be extra to these risks as it has been shown “predominantly generate
misinformation” (Porter, et al., 2016, p.36).
This discussion is not to give the impression that Canadian police are consistently
engaging in unethical practices, or that the Mr. Big investigative technique is ‘bad’. Rather, the
challenges to the admissibility of Mr. Big confessions have commonly been dismissed in the
courts, only occasionally have the courts or precedent shown to express reservations about the
technique (Hunt, & Rankin, 2014, p.327). Although, there have been further advances by the
SCC to encourage the Canadian police to transition to a nondeceptive, information-gathering
model of police interrogation practice (PEACE) (Porter, et al., 2016, p.40). This represents the
process and traits of preparation, planning, engagement, explanation, account, closure, and
evaluation which has alienated some of the ethical stress that was previously ensuing in
interrogations (Porter, et al., 2016, p.40).
However, some research suggests that even further and higher standards for Mr. Big
operations are necessary due to their realistic and significant potential of these investigations to
produce unreliable or false confessions that would bring the administration of justice into
disrepute (Hunt, & Rankin, 2014, p.322). Other researchers have suggested that further
safeguards of Mr. Big operations should consist of requiring the operations to be judicially
preapproved. Further, Mr. Big operations should be corroborated by significant additional
evidence where police should make their awareness and perceptiveness to the risk of infringing
rights of the accused a primary concern (Sukkau, & Brockman, 2015, p. 76). Since the landmark
case of R v Hart [2014], significant concerns have been addressed and further guidance has been
given in regard to these unique undercover investigations. Nonetheless, there is still further

67
clarity needed on the issue of how reliable or truthful a confession may be at its core, regardless
of the court’s determinations of admissibility.
Recommendations and Conclusion
Despite the safeguards Canadian police and courts have put in place, there is still the fact
that there is a substantial degree of unreliability of self-incriminating statements that are being
obtained through Mr. Big operations. This unreliability is found when a target may confess to a
crime he or she did not commit or was unreasonably induced into making a statement, thus
creating room for false confessions leading to wrongful convictions that ultimately undermined
the due process of the Canadian criminal justice system. It is clear that there is value in
undercover investigations and that Mr. Big operations have been able to successfully solve many
crimes in Canada. However, an individual’s rights cannot be compromised in this pursuit,
especially because it can pose a significant risk for wrongful convictions or Charter
infringements of the suspect. Mr. Big Operations raise concerns about its sometimes-oppressive
tactics and conduct. Within this context, the SCC has deemed legal prejudice, reliability of
confessions, and police misconduct as primary areas of concern (Murphy, & Anderson, 2016, p.
47). Police misconduct in general has been addressed more recently, but still requires further
common law limitation and refinement of conduct and duty. Pertaining to officer discretion in
the advancement of Mr. Big operations, it is important to realize there is a crucial difference
between law enforcement using character traits or situational opportunities to investigate and
develop a rapport with someone and using tactics that coerce or prey on the target’s
vulnerabilities and induce them into confessing.

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Recommendation One
To further advance the protection of individual rights and freedoms in light of undercover
operations, Canadian courts should continue to take steps in creating common law rules for the
collection of evidence (Hunt, & Rankin, 2014, p.335). Given the widespread movements
demanding police accountability such as Black Lives Matter (BLM) and the negative climate
surrounding law enforcement today such as #Defund the police, it is no secret that police
misconduct is an ongoing concern. It is evident that this misconduct is more likely to occur
‘behind the scenes’ where the public is unable to hold law enforcement accountable. This would
mimic the structure and environment of Mr. Big operations where it is reasonable to consider
that the secretive strategically complex technique would create a similar breeding ground for
misconduct.
Encouraging alternative approaches of legislative reform or legislative actions in the courts in the
face of such controversial and risky tactics could further address and control the problems related
to police misconduct we see today and aid in bringing back legitimacy and accountability to the
public-police relationship (Hunt, & Rankin, 2014, p.335). This is to say that due to the very
nature of the Mr. Big technique, it is predisposed to serious and sensitive issues that are readily
available for the courts to scrutinize. It is also fair to ask the courts to create such a limitation
protection through the establishment of a specific rule, as seen in R v Hart to help secure the
limitations of law enforcement and an accused’s Charter rights (Murphy, &Anderson, 2016,
p.47).
Recommendation Two
Legal rights in the Canadian Charter, specifically section 7 and section 11(d), interact
with particular concepts of this investigation technique that truly call into question the
seriousness of these risks that may interfere with a fair process of justice. It is therefore

69
important that police agencies establish guidelines to ensure that Mr. Big operations do not
inadvertently infringe on a target’s Charter rights. A target is afforded the right to silence and the
right to security of the person, along with the presumption of innocence, any police tactics or
conduct that would encroach on the Charter values such as autonomy, privacy, fairness, etc. that
would disadvantage the target. Since the Charter is the supreme law of Canada, citizens are
afforded the rights, freedoms, and protections under the Constitution. There must only be
specific circumstances for any infringements to be justified. Infringements that likely cannot be
justified under the circumstance of a Mr. Big investigation. Therefore, if undercover operatives
are using harmful tactics, it places substantial pressure on the individual to the point it engages
the Charter and could potentially constitute an unjustifiable Charter infringement. Thus, bringing
the effective purpose and constitutionality of this technique into debate (Moore, et al., 2009,
p.371).
Recommendation Three
In Canada. it is not unheard of to see offenders and the accused exonerated based on
DNA evidence being retested years after a person has confessed (Moore, et al., 2009, p.400).
This fact demonstrates that the possibly of false confessions and a miscarriage of justice is a
legitimate plausible outcome to consider (Moore, et al., 2009, p.400). The personal, physical, and
mental characteristics of the target of a Mr. Big investigation need to be considered throughout
the investigation as their own perception and cognitive functioning will impact how police
tactics are received. This further emphasizes the need for the Canadian justice system to
distinguish all the methods of interrogations that are approved, and to place reasonable
limitations on police conduct. With an explicit direction from SCC or legislation, it would reduce
or eliminate the investigations reliance on false evidence or feeling the need to resort to police
trickery and intruding tactics in order to “solve” the crime (Moore, et al., 2009, p.400). With that

70
being said, alternative extensive measures may involve videotaping the interrogations through
body cameras or alternative technology which would change the reliability of the investigation
for the better due to the availability of alternative physical evidence (Moore, et al., 2009, p.400).
Recommendation Four
Further safeguards such as more stringent procedures for evaluating evidence and
sufficient consideration of vulnerable and high-risk populations are needed in Mr. Big operations
(Smith, et al., 2009, p187). As law is always adapting and evolving, the new evidentiary rule put
forth in R v Hart [2014] created the understanding around the limitation of Mr. Big operations
and the link to Charter rights. Some criticize the SCC as they argue this approach would be better
with a more “generally articulated” rule of evidence at a higher level that could have applied to
all undercover investigations that occur rather than just Mr. Big operations specifically (Hunt, &
Rankin, 2014, p.334). However, due to unique circumstances of the R v Hart [2014] case, and
the characteristics of these operations as a whole, the Court did a positive job in clarifying
section 7 and protecting individual rights. By determining all Mr. Big confessions are to be
considered inadmissible until the Crown can demonstrate the accurate balance of probabilities
and can weigh the probative and prejudicial value of the evidence, this ensures a target will be
given a fair trial and the resulting confession would be reliable (Puddister et al, 2012, p.400).
Recommendation Five
To help further refine Mr. Big operations and ensure the protection of Charter rights,
Parliament should put forth legislative guidelines to address all undercover operations along with
the SCC common law. This does not have to be complicated but secured guidelines as simple as
instructing judges to carefully consider the reliability of evidence by examining the presence of
inducements or threats made by police undercover operatives would make a considerable
difference (Puddister, et al., 2012, p.401). Some even suggest that police should provide “the

71
provincial solicitor general or minister of public safety with reports that evaluate the costs and
benefits of the technique” so that there is a way to keep record and measure its effectiveness and
use (Puddister, et al., 2012, p.401). It is important to note in this argument that there have not
been many known cases where a wrongful conviction occurred from the use of a Mr. Big
operation. However, there have been Mr. Big cases where confessional or forensic evidence that
was used has been re-called into question in which trials have been thrown out, or instances of
false confessions have occurred (R v Hart, 2014, 2 SCR 544, p. 62).
There is considerable value in Mr. Big operations. It is a complex and well-established
technique that has advanced undercover policing and has become what the Canadian police call
“effective” and “successful” in convicting criminals. Although, given the evidence of the
plausible risks associated with the Mr. Big operations, there is reasonable need for concern in
which legislative guidelines and further common law precedent should establish further
thresholds and limitations. In Canada, the police should also continue to work to improve
training with respect to undercover operations to raise awareness and sensitivity of psychological
dimensions involved in false confessions and the risks involved in these investigations
(Puddister, et al., 2012, p.402). Although a valuable investigative technique, Mr. Big operations
require oversight and further judicial guidance. Mr. Big operations are a borderline Charter
infringing technique and need to be used carefully. The operation itself may not infringe an
individual’s Charter rights directly, however, the very nature of the operation exposes the
accused to unique circumstances with an increased risk of opportunity for injustice. Any police
conduct that engages the Charter in a way that threatens a target’s rights should be examined
more closely and placed under legal scrutiny.

72
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