COURT FILE NO.: CR-18-30000602-0000

DATE: 20220118

ONTARIO SUPERIOR COURT OF JUSTICE

BETWEEN:

HER MAJESTY THE QUEEN

– and –

AAMALALL MOOTOO

Anna Gilmer, for the Crown

Aamalall Mootoo, Self-represented

Erin Dann, Amicus Curiae

HEARD at Toronto: March 25, 26, 29, 30, 31 and April 1, 2021

Publication Ban

Subject to any further Order by a Court of competent jurisdiction, an Order has been made in this proceeding that the identity of the complainant and any information that could disclose such identity shall not be published in any document or broadcast in any way, pursuant to s. 486.4(1) of the Criminal Code, R.S.C., 1985, c. C-46.

REASONS FOR DECISION ON s. 8 OF THE CHARTER

DAVIES J.

A. Overview

[1] H.J. met someone named “Jay” online and communicated with him for a few days before they met in person on March 23, 2017. H.J. stayed at Jay’s apartment that night. H.J. and Jay continued to communicate through various messaging applications and spoke on the phone in the days after she stayed at his apartment. H.J. was only 15 years old at the time.

[2] On March 30, 2017 H.J. went to the police and reported that Jay sexually assaulted her when she was at his apartment. H.J. also told the police that Jay had been sending her sexually explicit messages, including some about H.J. engaging in prostitution when she turned 16. H.J. showed the police the messages she received from Jay. H.J. also gave the police her phone and gave them permission to use her online profiles to communicate with Jay.

[3] Between March 30 and April 19, 2017, the police impersonated H.J. and exchanged hundreds of messages with Jay through BlackBerry Messenger (“BBM”). The police took screenshots of Jay’s messages. The police did not obtain a warrant to use H.J.’s online profile to communicate in an undercover capacity with Jay or to capture Jay’s messages.

[4] Using H.J.’s BBM account, the police arranged to meet Jay on April 19, 2017. Mr. Mootoo showed up and was arrested. The police seized a cell phone from Mr. Mootoo during his arrest. Without obtaining a warrant, the police searched Mr. Mootoo’s phone incident to his arrest and took screenshots of every conversation in five applications: BBM, Snapchat, Instagram, Kik, and Plenty of Fish. Several weeks later, the police got a warrant to search Mr. Mootoo’s phone.

[5] The police executed a search warrant at Mr. Mootoo’s apartment shortly after his arrest on April 19, 2017. They seized identification belonging to Mr. Mootoo. They also seized clothing that appears to match the clothing worn by the person H.J. met on March 23, 2017.

[6] Mr. Mootoo is charged with eight offences including sexual assault, sexual interference, possession of child pornography, luring a person under the age of 16 for the purpose of facilitating a sexual offence, and procuring a person under the age of 18 to engage in prostitution. It is the Crown’s theory that Mr. Mootoo is Jay. It is the Crown’s position that Mr. Mootoo’s messages to H.J. (including messages he sent while the police were impersonating H.J.) make out the actus reus of possessing child pornography, procuring a person under the age of 18 to engage in prostitution, and luring a person under the age of 16 for the purpose of facilitating a sexual offence.

[7] Mr. Mootoo denies that he is Jay. Mr. Mootoo denies that he ever communicated with H.J. He also denies the phone the police seized and analyzed was his phone. At trial, the burden will be on the Crown to prove that Mr. Mootoo is the person H.J. met on March 23, 2017 and that Mr. Mootoo is the person who communicated with H.J. For the purpose of these Charter applications, Mr. Mootoo is entitled to rely on the Crown’s theory that he sent the messages the police seized from H.J.’s account and that the phone seized during his arrest belonged to him: R. v. Jones, 2017 SCC 60, [2017] 2 S.C.R. 696, at para. 19.

[8] Amicus raised several issues in relation to the searches conducted by the police. Amicus argued that the police violated Mr. Mootoo’s right to be free from unreasonable search and seizure when they impersonated H.J. to communicate with Mr. Mootoo and captured his messages without a warrant. Amicus further argued that the search of Mr. Mootoo’s phone incident to arrest violated s. 8 of the Canadian Charter of Rights and Freedoms because it was too broad and not done for an authorized purpose. Amicus also argued that the forensic analysis of Mr. Mootoo’s phone after the police obtained a warrant was unreasonable because the police searched for items on the phone that were not authorized. Finally, Amicus argued the search of Mr. Mootoo’s apartment was unreasonable because the police seized items that were not authorized in the warrant.

[9] Mr. Mootoo objected to Amicus participating in his trial. He did not adopt or endorse the submissions Amicus made on this application. Nonetheless, Mr. Mootoo confirmed that he wanted all the evidence seized by the police excluded. In relation to the forensic analysis of the phone, Mr. Mootoo argued that the police never got a warrant to search the phone and that the warrant filed on the application was forged.

[10] The Crown argued that the police were entitled to impersonate H.J., communicate with Mr. Mootoo, and capture Mr. Mootoo’s messages without a warrant. The Crown argued Mr. Mootoo did not have a reasonable expectation of privacy in the messages seized from H.J.’s phone, so his rights under s. 8 of the Charter were not engaged by the undercover investigation. The Crown also argued that police were entitled to search Mr. Mootoo’s phone incident to his arrest and the warrantless search of his phone did not violate his rights under s. 8 of the Charter. Finally, the Crown argued that the warrants for Mr. Mootoo’s phone and apartment were valid and executed in a reasonable manner.

[11] To avoid any delay in the trial, I gave a brief oral ruling in which I found the following:

i. Mr. Mootoo had a reasonable expectation of privacy in the messages seized from H.J.’s BBM account while the police were impersonating her. The warrantless seizure of Mr. Mootoo’s messages during the undercover investigation violated his right to be free from unreasonable search and seizure. The admission of the text messages seized from H.J.’s phone would bring the administration of justice into disrepute.

ii. The warrantless search of Mr. Mootoo’s phone incident to his arrest violated his rights and the admission of the screenshots taken during that search would bring the administration of justice into disrepute.

iii. The warrant to search Mr. Mootoo’s phone was valid and the information extracted during the forensic analysis of the phone (other than messages from the period during which the police were impersonating H.J.) is admissible.

iv. The warrant to search Mr. Mootoo’s apartment was valid and the items seized during that search are admissible.

[12] These are my reasons for my earlier ruling.

B. Did the undercover communications using H.J.’s phone violate Mr. Mootoo’s right to be free from unreasonable search and seizure?

[13] On March 30, 2017, H.J. reported she had been sexually assaulted by someone she met online. H.J. gave a videotaped statement to Det. Braganza and gave Det. Braganza her phone. H.J. signed a consent authorizing the police to assume her online identity and use her Instagram, Kik, Facebook and BBM accounts.

[14] Det. Braganza took over H.J.’s online profile in BBM and, pretending to be H.J., communicated with Mr. Mootoo for close to three weeks. Det. Braganza simply continued the online conversation H.J. was having with Mr. Mootoo when she gave him her phone. Det. Braganza testified the whole point of taking over H.J.’s account was to gather evidence against Mr. Mootoo. Det. Braganza took steps to ensure the tone and content of his messages were consistent with H.J.’s earlier messages. He asked H.J. what Mr. Mootoo knew about her and her family so he could convincingly impersonate H.J.

[15] The police took screenshots of the messages Mr. Mootoo sent to H.J.’s account while her phone was in their possession. In total, the police took over 650 screenshots of the messages sent to or received from Mr. Mootoo while they were impersonating H.J. The police did not obtain judicial authorization to impersonate H.J. or to capture Mr. Mootoo’s messages.

[16] The issue for me to decide is not whether the police are allowed to impersonate a complainant and communicate electronically with a suspect in an investigation. The question is whether the police needed prior judicial authorization to undertake an undercover operation of that nature in this case, which turns on whether Mr. Mootoo had a reasonable expectation of privacy in his communications with H.J.

[17] Det. Braganza testified that he was relying on H.J.’s consent as his legal authority to communicate with Mr. Mootoo and take screenshots of Mr. Mootoo’s messages. H.J. did not participate in any online conversation with Mr. Mootoo once Det. Braganza had her phone. Her consent is, therefore, not relevant to whether Mr. Mootoo had a reasonable expectation of privacy in the messages he sent or to whether the police needed a warrant to capture his messages.

[18] The burden is on Mr. Mootoo to establish he had a reasonable expectation of privacy in the messages seized from H.J.’s phone. Mr. Mootoo must show he had a direct interest in the messages seized by the police, he had a subjectively held expectation of privacy in the messages, and that his expectation of privacy was objectively reasonable: R. v. Marakah, 2017 SCC 59, [2017] 2 S.C.R. 608, at paras. 11-12. The Crown concedes that Mr. Mootoo had a direct interest in the messages he sent to H.J.’s account. The Crown also concedes that Mr. Mootoo had a subjective expectation of privacy in his messages to H.J. But the Crown argues Mr. Mootoo’s expectation of privacy was not objectively reasonable and, as a result, his rights under s. 8 of the Charter were not engaged.

[19] If the Crown is right, the police did not need prior judicial authorization to assume H.J.’s identity and communicate with Mr. Mootoo and the messages they captured are admissible. If, however, Mr. Mootoo did have an objectively reasonable expectation of privacy in the messages he sent to H.J.’s account, the seizure of those messages is presumptively unreasonable because the police did not have a warrant to capture his messages from H.J.’s account.

[20] Whether Mr. Mootoo’s expectation of privacy is objectively reasonable is a normative question: should Canadians in Mr. Mootoo’s position enjoy an expectation of privacy in their electronic communications? To answer this question, I must consider all the circumstances including (a) the nature of the information shared, (b) the place from which the messages were seized, (c) whether Mr. Mootoo retained control over the messages or their content once they were sent to H.J., (d) the nature of Mr. Mootoo’s relationship with H.J., and (e) the nature of the undercover investigation: Marakah, at para. 24; R. v. Mills, 2019 SCC 22, [2019] 2 S.C.R. 320, at para. 20. I must also consider the policy implications of deciding that Mr. Mootoo does or does not have a reasonable expectation of privacy in this case: Marakah, at paras. 46-52.

(a) Nature of Mr. Mootoo’s messages to H.J.

[21] The right to be free from unreasonable search and seizure is intended to protect a “biographical core” of information that individuals would want to keep private from the state, including information that tends to reveal intimate details about their lifestyle and personal choices: R. v. Plant, 1993 CanLII 70 (SCC), [1993] 3 SCR 281, at p. 293. Private text communications can reveal a great deal about an individual’s personal choices and lifestyle. In fact, sending text messages is one of the most private means of communication. As the Supreme Court noted, “it is difficult to think of a type of conversation or communication that is capable of promising more privacy than text messaging”: Marakah, at para. 35.

[22] When assessing whether the communications in question are private for the purpose of s. 8 of the Charter, the focus must be on whether there was a potential that Mr. Mootoo would share personal information with H.J. in his electronic communications: Marakah, at para. 32. The actual content of the messages seized by the police is not relevant: Marakah, at para. 32.

[23] It was very likely Mr. Mootoo would share personal information with H.J. in his messages. Mr. Mootoo sent his messages through a private messaging application to H.J. only and I am satisfied that Mr. Mootoo only expected H.J. to read them. Mr. Mootoo did not send his messages to multiple people or post them in a public forum. Mr. Mootoo did not know Det. Braganza had assumed control of H.J.’s account and did not expect the police to read and copy his messages. The medium through which Mr. Mootoo communicated with H.J. supports his claim that he had an objectively reasonable expectation of privacy in the messages he sent to her account.

(b) Place from which the messages were seized

[24] The place searched can help inform whether someone has a reasonable expectation of privacy in the items seized: R. v. Tessling, 2004 SCC 67, [2004] S.C.R. 432, at para. 22. For example, we have a very high expectation of privacy in our home and its contents. But the concept of “place” is more complicated in the context of electronic communications. On the one hand, electronic communications can be seen as akin to private conversations between two people in a private virtual room. On the other hand, electronic communications are often stored in and accessible from more than one account or device at the same time, giving more than one person control over the messages: Marakah, at paras. 28-29. Either way, the Supreme Court of Canada has been clear that an individual can retain a reasonable expectation of privacy over electronic messages that have been sent and are seized from the recipient’s phone: Marakah, at para. 41. A reasonable expectation of privacy in electronic communications is not an all or nothing proposition. It exists on a spectrum: Tessling, at para. 22. The

[25] In my view, the place of the search is less important in the context of electronic communications than it might be in some other contexts. It remains a factor but it is by no means determinative. The fact the police seized the messages from H.J.’s phone should not, from a normative perspective, defeat Mr. Mootoo’s claim that he reasonably expected his messages to remain private even after they were sent. I find that Mr. Mootoo’s reasonable expectation of privacy was not extinguished when he sent the messages to H.J.

(c) Mr. Mootoo’s ability to control information sent to H.J.

[26] The Crown argues that when someone communicates with a young person online for the purpose of facilitating a criminal offence, they do not enjoy a reasonable expectation of privacy in their sent messages, because there is a risk the young person will turn those messages over to the police. The Supreme Court of Canada has repeatedly and expressly rejected the argument that a person loses their expectation of privacy over information they share with others because the recipient could disclose the information to someone else: R. v. Duarte, 1990 CanLII 150 (SCC), [1990] 1 S.C.R. 30, at pp. 43-44; Marakah, at para. 41. The right to be free from unreasonable search and seizure has nothing to do with protecting individuals from the threat that people will divulge private information to others. The right to be free from unreasonable search and seizure protects us from the police intercepting our private communications: Duarte, at pp. 43-44. People are entitled to assume the state will not record their private communications unless authorized to do so by a judicial officer: Duarte, at p. 46.Accepting the risk that the recipient of a text message could disclose it to someone else does not mean the sender assumes the risk that the state will intercept their electronic conversation: Marakah, at paras. 40 and 45.

[27] Nonetheless, control remains a relevant factor when assessing whether Mr. Mootoo’s subjective expectation of privacy is objectively reasonable. Individuals exercise control over the information they send via text message by choosing how, when, and to whom they communicate: Marakah, at para. 39. The extent to which Mr. Mootoo tried to or was able to control the information he shared with H.J. is a relevant factor: Marakah, at paras. 38-39; R. v. Cole, 2012 SCC 53, [2012] 3 S.C.R. 34, at paras. 54-58.

[28] Mr. Mootoo chose to continue to share information with H.J. after meeting her in person (or so the Crown alleges). He also chose to share information with H.J. through a private messaging application. I have already found that Mr. Mootoo only expected H.J. to read his messages. These facts support a finding that Mr. Mootoo was exercising control over his personal information and had a reasonable expectation of privacy in his messages.

[29] There is also evidence that Mr. Mootoo deleted or retracted messages he sent to H.J. The officers involved in sending messages from H.J.’s account both testified that from time to time Mr. Mootoo retracted messages he sent. When Mr. Mootoo retracted a message, it was deleted from H.J.’s account. Had the police not created a permanent record of Mr. Mootoo’s messages by taking screenshots, the retracted messages would not have been available from H.J.’s account. Mr. Mootoo was continuing to exercise control over the information he shared electronically with H.J. when he chose to retract his messages, which further supports a finding that Mr. Mootoo had a reasonable expectation of privacy in the messages he sent to H.J.

(d) Nature of Mr. Mootoo’s relationship with H.J.

[30] The Crown argues that, from a normative perspective, someone in Mr. Mootoo’s position ought not to enjoy a reasonable expectation of privacy in his communications with H.J. The Crown argues that online communications between an adult and a child should only attract an objectively reasonable expectation of privacy if their relationship is worthy of protection. The Crown argues that the relationship between H.J. and Mr. Mootoo is not worthy of protection because Mr. Mootoo was communicating with H.J., who was only 15 years old, for the purpose of facilitating a criminal offence.

[31] Mr. Mootoo denies he knew H.J. was 15 years old. He made comments during the application that H.J. told him she was older. However, the Crown’s argument relies, at least in part, on the fact that H.J. was a child. The Crown’s position is that, from a normative perspective, the age of the recipient of a message is relevant to whether the sender has a reasonable expectation of privacy in their online communications. For the purpose of this application only, I will therefore assume H.J. was a child in March 2017 and Mr. Mootoo knew her age in order to give full consideration to the Crown’s position. Of course, the burden will be on the Crown at trial to prove H.J.’s age beyond a reasonable doubt and that Mr. Mootoo knew her age when he was communicating with her.

[32] The Crown relies heavily on the Supreme Court of Canada’s decision in Mills to support its position that s. 8 only protects communications between adults and children engaged in relationships worthy of protection. In Mills, the police created an email and Facebook page for a fictitious 14 year-old-girl named Leann. A month later, Mr. Mills contacted Leann. The police did not initiate the conversation with Mr. Mills and simply responded to Mr. Mills’ messages. The police communicated with Mr. Mills as Leann for two months. During that time, Mr. Mills sent Leann sexually explicit photos. The police took screenshots of the messages between Mr. Mills and Leann. Mr. Mills was eventually arrested and charged with luring a child. Mr. Mills argued the police needed judicial authorization to seize his messages to Leann. The Supreme Court held that Mr. Mills had a subjective expectation of privacy in his communications with Leann: Mills, at para. 17. However, the Court found that his expectation of privacy was not objectively reasonable. The two decisive factors in the Court’s conclusion that Mr. Mills did not have a reasonable expectation of privacy were the nature of the relationship between the parties and the nature of the investigative technique used: Mills at para. 20.

[33] In terms of the nature of the relationship, the Court recognized that children are particularly vulnerable to sexual violence and messaging applications provide greater opportunities to sexually exploit children: Mills at para. 23. The Court also recognized that notwithstanding these risks, most relationships between adults and children are worthy of protection against state intrusion: Mills at para. 26. In the end, the Court held that the relationship between Mr. Mills and the undercover officer posing as Leann was not worthy of protection because Mr. Mills believed the undercover officer to be a child and that they were strangers. In other words, Mr. Mills chose to send personal information to a child who was a complete stranger without taking steps to confirm the identity of the recipient or ensure confidentiality.

[34] Det. Braganza testified that, in his view, Mr. Mootoo and H.J. were strangers. He testified, “I don’t consider someone friends until they meet face to face.” Det. Braganza acknowledged that Mr. Mootoo and H.J. had met in person. Det. Braganza acknowledged that H.J. stayed overnight at Mr. Mootoo’s apartment. Det. Braganza acknowledged that they continued to communicate after meeting in person. But he maintained that he did not consider them to be friends when he assumed H.J.’s online identity and communicated with Mr. Mootoo.

[35] I do not accept Det. Braganza’s description of Mr. Mootoo’s relationship with H.J. While Mr. Mootoo and H.J. may not have known each other long, they were not strangers in the sense the Supreme Court used the term in Mills. Mr. Mootoo and H.J. had communicated by text for several days before meeting in person. They spent the night at his apartment. They continued to communicate by text and by telephone after they met. By the time the police took over H.J.’s BBM account, Mr. Mootoo knew H.J. was a real person and had been communicating with her for a couple of weeks. They were not strangers.

[36] In fact, Det. Braganza relied on the existing relationship between Mr. Mootoo and H.J. to advance the investigation. Det. Braganza continued the conversation H.J. was already having with Mr. Mootoo when she turned her phone over to the police. Det. Braganza consulted with H.J. about what she and Mr. Mootoo had talked about so he could impersonate her convincingly. I reject Det. Braganza’s evidence that Mr. Mootoo and H.J. were strangers. I find that for the purpose of the s. 8 analysis, Mr. Mootoo and H.J. were friends.

[37] The Crown argues that even if Mr. Mootoo and H.J. were not strangers, their relationship is not worthy of protection because Mr. Mootoo was communicating with H.J. for a criminal purpose.

[38] By the end of his interviews with H.J. and her sister K.J., Det. Braganza had reasonable grounds to believe Mr. Mootoo had committed several criminal offences, including sexual interference, luring a child to engage in a sexual offence, and procuring a child to engage in prostitution. Det. Braganza read some of the sexually explicit messages Mr. Mootoo sent H.J. before March 30, 2017. Det. Braganza also heard a recording of a sexually explicit phone call between H.J. and Mr. Mootoo.

[39] Even if some of Mr. Mootoo’s communications with H.J. were criminal in nature that does not defeat the reasonableness of his expectation of privacy in those communications. The Supreme Court of Canada has repeatedly held that the analysis of whether a reasonable expectation of privacy exists must be content neutral. The analysis turns on the privacy of the location or thing searched, not the legality or illegality of the items sought or the information obtained: Marakah, at para. 48; R. v. Spencer, 2014 SCC 43, [2014] 2 S.C.R. 212, at para. 36; R. v. M(A), 2008 SCC 19, [2008] 1 S.C.R. 569, at para. 72; R. v. Buhay, 2003 SCC 30, [2003] 1 S.C.R. 631, at para. 19; Duarte, at pp. 51-52; and R. v. Wong, 1990 CanLII 56 (SCC), [1990] 3 S.C.R. 36, at p. 50.

[40] For example, in Wong, the police received information that people may be using a hotel room for illegal gambling. The police installed a video camera in the room without prior judicial authorization. The Supreme Court held that when assessing whether someone had a reasonable expectation of privacy, the fact they were engaged in illegal activity is irrelevant. The question is not whether someone engaged in illegal activity in a hotel room has a reasonable expectation of privacy. Rather, the question must be framed “in broad and neutral terms”: Wong, at p. 50. In Wong, the question was whether, in a free and democratic society, someone who retires to a hotel room has a reasonable expectation of privacy.

[41] Similarly, the Supreme Court did not rely on the illegal nature of the communication in Mills as a basis to conclude that Mr. Mills had no expectation of privacy in his messages to Leann. The Court was interested in whether and how they knew each other, not whether their relationship involved illegal activity.

[42] Finally, in Marakah, the text messages seized by the police were about trafficking firearms. The fact that Mr. Marakah and Mr. Winchester were communicating for the purpose of carrying out a criminal offence did not defeat Mr. Marakah’s reasonable expectation of privacy in his messages. The Court reiterated that the content of the messages seized could not justify an unreasonable violation of privacy: Marakah, at para. 48.

[43] I find that Mr. Mootoo and H.J. were not strangers. This case is not comparable to Mills where the target was communicating with a fictitious child that Mr. Mills had never met. The nature of the relationship between Mr. Mootoo and H.J. supports a finding that he had an objectively reasonable expectation of privacy in their communications.

(e) Nature of the Police Investigation

[44] The nature of the investigative technique was the second factor the Supreme Court considered decisive in Mills. The police are required to obtain judicial authorization before employing an investigative technique that has the potential to violate a target’s privacy interests: Mills, at para. 28. However, if there is no possibility an investigative technique will violate the target’s privacy interests, the police do not need prior judicial authorization.

[45] In Mills, the Court found that creating a fictitious Facebook account for a fictitious child and communicating with Mr. Mills could not infringe his privacy because adults do not have a reasonable expectation of privacy with children who are strangers to them. The police knew that anyone who reached out to Leann was a stranger to her (because she did not exist). As a result, the police investigation could not infringe anyone’s privacy rights or “significantly reduce the sphere of privacy enjoyed by Canadians”: Mills, at para. 20.

[46] The analysis in Mills only relieves the police from the requirement to obtain judicial authorization before intercepting private communications if an adult suspect is communicating online with a child who is a stranger and the police know they are strangers before any communication is intercepted: Mills at para. 24. Mr. Mootoo’s case does not fall into that narrow exemption. Mr. Mootoo and H.J. were not strangers and the police knew that before they intercepted Mr. Mootoo’s messages. The police did not create a fictitious child. The police impersonated an actual person. The police deliberately used the existing relationship between Mr. Mootoo and H.J. to further their investigation. In other words, the police knew, or at least ought to have known, their investigation would potentially breach Mr. Mootoo’s privacy rights. The fact that the police impersonated a real person and insinuated themselves in an existing relationship enhances Mr. Mootoo’s claim to a reasonable expectation of privacy.

(f) Policy Considerations

[47] Given the focus of the analysis is whether a reasonable expectation of privacy ought to be recognized, courts often consider the policy implications of recognizing or not recognizing an expectation of privacy in a particular situation.

[48] For example, in Marakah, the Supreme Court expressly considered the policy implications of applying a “content neutral” approach to privacy in cases like this involving sexual predators communicating online with children. It was argued in that case that the Court should not recognize an expectation of privacy communications in cases involving online predators because of the impact that would have on law enforcement. The Supreme Court recognized that the state’s interest in effective law enforcement is a relevant consideration to be balanced against an individual’s privacy interests. However, the Court held that constitutionally protected privacy in electronic conversations should not be lightly denied, regardless of law enforcement’s interest in having unfettered access to text messages: Marakah, at para. 53. The Court held that adopting a content neutral approach to the analysis of privacy under s. 8 of the Charter does not mean that text messages sent by sexual predators to children will not be allowed into evidence. The police can obtain a warrant to access the messages to avoid any breach of s. 8. Alternatively, if the police do not obtain a warrant, the Crown can argue the warrantless seizure does not constitute a breach of s. 8 or, if it does, that the evidence should still be admitted under s. 24(2) of the Charter: Marakah at paras. 48-52.

[49] In her concurring reasons in Mills, at paras. 36-65, Karakatsanis J. noted that requiring the police to obtain a warrant to engage in undercover investigations of the sort carried out in Mills would be impractical and would significantly undermine the ability of police to proactively identify predators before they victimize children. In most cases like Mills, the police would not be able to get a prior judicial authorization because the police have not yet identified a target and do not have evidence that an offence has been committed. The fictitious accounts are created in order to identify people who are inclined to lure children for a sexual purpose before an actual child was victimized.

[50] The concern expressed in Mills that requiring police to get a warrant would unduly constrain or undermine undercover investigations into Internet luring does not arise in Mr. Mootoo’s case. When the police assumed H.J.’s identity for the purpose of communicating with Mr. Mootoo, they were in a position to apply for a warrant. The police had received a criminal complaint from H.J. They had reasonable grounds to believe several offences had been committed against H.J. The police had information about Mr. Mootoo’s identity including his contact information in various messaging applications. The police could have applied for judicial authorization to intercept his communications without compromising their investigation.

[51] I find that the state’s interest in effective law enforcement cannot override the presumption that the police must get prior judicial authorization to intercept private communications in the circumstances of this case.

(g) Conclusion

[52] Having considered all the circumstances, I find that Mr. Mootoo had an objectively reasonable expectation of privacy in his messages to H.J. The police were required to get prior judicial authorization before infringing Mr. Mootoo’s privacy rights by communicating with him in an undercover capacity and taking screenshots of his messages. The warrantless seizure of those messages from H.J.’s phone violates Mr. Mootoo’s right under s. 8 of the Charter to be free from unreasonable search and seizure.

C. Search of mr. mootoo’s phone incident to arrest

[53] Mr. Mootoo was arrested on April 19, 2017. He was holding a phone when he was arrested, which was seized from him. The arresting officer turned Mr. Mootoo’s phone over to Detective Braganza.

[54] Without obtaining a warrant, Det. Braganza searched Mr. Mootoo’s phone incident to his arrest. Det. Braganza changed the password for the phone so he could continue to access it during his investigation. He also took screenshots of every conversation in five applications: BBM, Snapchat, Instagram, Kik, and Plenty of Fish. Several weeks later, the police got a warrant to search Mr. Mootoo’s phone.

[55] The warrantless search of Mr. Mootoo’s phone is presumptively unreasonable. The burden is on the Crown to show the search was reasonable even though the police did not have a warrant. A cell phone search incident to an arrest will be reasonable if the arrest was lawful, if the police had an objectively reasonable law enforcement purpose for searching the phone, if the search was tailored to the law enforcement purpose and if the police took detailed notes of how the search of the phone was conducted: R. v. Fearon, 2014 SCC 77, [2014] 3 S.C.R. 621, at para. 83.

[56] I am satisfied Mr. Mootoo’s arrest was lawful. The police had reasonable and probable grounds to believe Mr. Mootoo had committed several offences against H.J. including sexual interference, invitation to sexual touching, and luring a child. The issues for me to decide are whether Det. Braganza had a valid law enforcement purpose to search Mr. Mootoo’s phone, whether the search was tailored to that purpose, and whether Det. Braganza adequately documented his search.

[57] In my view, Det. Braganza was authorized to conduct a cursory search of Mr. Mootoo’s phone incident to arrest to preserve evidence. He was entitled to change the password to the phone and the online messaging applications to preserve evidence until a warrant could be obtained. However, the search Det. Braganza conducted was more extensive than authorized under his common law power. And Det. Braganza failed to adequately document his search. I therefore find the search of Mr. Mootoo’s phone incident to his arrest was unreasonable and violated his rights under s. 8 of the Charter.

(a) Law enforcement purpose for the search of Mr. Mootoo’s phone

[58] The police are entitled to search a cell phone incident to arrest for three reasons. First, the police can search a cell phone incident to arrest if it is necessary to protect the police, the suspect, or the public. Second, the police can search a cell phone incident to arrest to preserve evidence of the offence under investigation. Third, the police can search a cell phone incident to arrest to discover evidence if there is a reasonable prospect that evidence of the offence will be found on the phone and if investigation would be stymied or significantly hampered without the ability to search the phone: Fearon, at paras. 22, 33, 80 and 83.

[59] The Crown argues that Det. Braganza was entitled to search Mr. Mootoo’s phone incident to arrest to both preserve evidence and discover evidence. I disagree. Det. Braganza testified his investigation would not have been impacted in any way if he had waited for a warrant to search Mr. Mootoo’s phone. None of the screenshots Det. Braganza took on April 19, 2017 were needed to advance his investigation. There is, therefore, no evidence the police investigation would have been stymied or hampered in any way if Det. Braganza had not conducted a warrantless search of Mr. Mootoo’s phone incident to his arrest. Det. Braganza was, therefore, not entitled to search the phone to discover evidence. Det. Braganza was only authorized to search Mr. Mootoo’s phone incident to his arrest to preserve evidence.

(b) Was the search of Mr. Mootoo’s phone tailored to the purpose of the search?

[60] Det. Braganza was required to tailor his search of Mr. Mootoo’s phone to the specific law enforcement purpose for which the search was authorized, namely to preserve evidence. While not a rule, a properly tailored search incident to arrest will usually focus on recently sent or received emails, texts, photos or call logs: Fearon, at para. 76. In most cases, only recent activity on the phone will have the “necessary link to the purposes for which prompt examination of the device is permitted”: Fearon, at para. 76.

[61] In my view, the search conducted by Det. Braganza was not tailored to the purpose of preserving evidence. Det. Braganza searched applications and captured messages that he had no basis to believe could afford evidence of the offences for which Mr. Mootoo had been arrested. And he did more than was necessary to preserve relevant evidence on the phone.

[62] When Det. Braganza took possession of the phone shortly after Mr. Mootoo’s arrest, it was not locked. Det. Braganza was concerned that the phone might be password protected and, if left unused, would automatically lock. So Det. Braganza changed the password for the phone so he could continue to access its contents even if it was password protected. Det. Braganza then searched the BBM application on Mr. Mootoo’s phone and took screenshots of all the messages between Mr. Mootoo and H.J. Several hours later, he searched four other web-based messaging applications: Snapchat, Instagram, Kik and Plenty of Fish. Det. Braganza took screenshots of every message in all four applications. Det. Braganza changed the password for Mr. Mootoo’s Snapchat, Instagram and Kik accounts. Det. Braganza also changed the email addresses associated with those accounts to his own Toronto Police Service email. Det. Braganza could not recall and had no note of changing the password and email address for Mr. Mootoo’s Plenty of Fish account. Det. Braganza testified he did not read the screenshots he took on Mr. Mootoo’s phone but assumed they would be saved in the photo gallery on the phone.

[63] Det. Braganza testified he did not access any text messages, email accounts, call logs or contacts in Mr. Mootoo’s phone during the search incident to arrest. Det. Braganza testified that he thought he needed a warrant to review call logs, text messages and contacts on Mr. Mootoo’s phone. He testified that he also thought he needed a warrant to read the screenshots he took of messages in BBM, Kik, Snapchat, Instagram and Plenty of Fish.

[64] I have significant concerns about Det. Braganza’s credibility. At Mr. Mootoo’s preliminary inquiry, Det. Braganza testified the police had not obtained a warrant to search Mr. Mootoo’s phone. That was not true. Det. Garrity obtained a warrant for Mr. Mootoo’s phone on April 26, 2017. Det. Braganza reviewed the Tech Crimes Unit’s forensic report on the content of Mr. Mootoo’s phone before the preliminary inquiry. Det. Braganza spent several days going through the 25,000 or 30,000 images downloaded from Mr. Mootoo’s phone.

[65] When asked to explain why he said that no warrant had been obtained for Mr. Mootoo’s phone at the preliminary inquiry, Det. Braganza said that he was confused. He said he could not find a copy of the warrant when he was preparing for the preliminary inquiry. He thought a warrant had been obtained but he had no notes of assigning the task of applying for a warrant to anyone on his team and could not find any reference to an application being submitted (or a warrant being obtained) in any officer’s notes. He said by the time he testified at the preliminary inquiry he was confused about whether a warrant had been obtained, even though he had reviewed the forensic report about Mr. Mootoo’s phone. I do not accept Det. Braganza’s explanation.

[66] First, Det. Garrity contradicted Det. Braganza on whether there was a record of the warrant application being prepared. Det. Garrity testified there are several entries in his notes about working on the search warrant application for Mr. Mootoo’s phone. He also recorded in his notes when he dropped Mr. Mootoo’s phone off at the Tech Crimes Unit after the warrant was issued. Det. Garrity testified that Det. Braganza never contacted him at the time of Mr. Mootoo’s preliminary inquiry to ask him about the warrant or for a copy of the warrant. I do not believe Det. Braganza’s testimony that he looked through the notes of the officers on his team and made inquiries but could not find any reference to a warrant application being submitted or a warrant being issued.

[67] Second, Det. Braganza did not say he was confused at the preliminary inquiry when given the chance to do so. Det. Braganza was pressed at the preliminary inquiry by Mr. Mootoo’s lawyer about why he had not obtained a warrant to search Mr. Mootoo’s phone. Rather than explaining his confusion, Det. Braganza said he did not think an analysis of Mr. Mootoo’s phone would add much to their investigation. Det. Braganza did not mention at the preliminary inquiry he had already reviewed the forensic report on the content of Mr. Mootoo’s phone. He did not mention that he thought a warrant had been issued but could not find a copy. He did not mention he had reviewed the notes of the officers on his team and could not find a reference to a warrant being requested. Instead, he maintained no warrant had been sought and left the false impression that Mr. Mootoo’s phone had not been analyzed. I find that Det. Braganza’s testimony at the preliminary inquiry was untruthful and misleading.

[68] Despite my concerns about Det. Braganza’s credibility, I accept that he changed the passwords on Mr. Mootoo’s messaging applications and took screenshots of all the messages in the five applications. Those steps were documented in his notes. Det. Braganza may well have done more during his search of the phone incident to arrest than was documented, but I am satisfied that, at a minimum, he changed the passwords and copied every message in the five applications. And based on that evidence alone, I find that the search of Mr. Mootoo’s phone incident to arrest was overly broad and not properly tailored to a valid law enforcement purpose.

[69] The common law power to search a phone incident to arrest only allows the police to conduct a search that is “required to be done promptly upon arrest in order to effectively serve the purpose of officer and public safety, loss or destruction of evidence, or discovery of evidence”: Fearon, at para. 75. To the extent that Det. Braganza was entitled to search Mr. Mootoo’s phone incident to arrest, his authority was limited to searches that needed to be done promptly to secure evidence.

[70] Det. Braganza communicated with Mr. Mootoo for several weeks using H.J.’s BBM account. He, therefore, had reason to believe that relevant evidence would be found in Mr. Mootoo’s BBM account. Det. Braganza also had evidence that H.J. and Mr. Mootoo had, at some point, used Instagram and Kik to communicate with each other. H.J. told the police she met Mr. Mootoo over Instagram in early March 2017. She said that she and Mr. Mootoo communicated over Kik for a short period initially before they started using BBM. Det. Braganza, therefore, had grounds to believe there would be relevant evidence in Mr. Mootoo’s Instagram and Kik accounts.

[71] Det. Braganza changed passwords for Mr. Mootoo’s phone as well as for his BBM, Instagram and Kik accounts. He did that to prevent anyone from logging into Mr. Mootoo’s accounts from a different device and deleting or retracting messages. Det. Braganza agreed that once the passwords were changed in the messaging applications, nobody could change or delete any information in those applications.

[72] I am satisfied that Det. Braganza was entitled to change the passwords for Mr. Mootoo’s phone and his BBM, Instagram and Kik accounts. That guaranteed any evidence on the phone or in the messaging applications would be preserved. In my view, once Det. Braganza had taken steps to preserve the relevant data on Mr. Mootoo’s phone, he was not entitled to open, read and copy the messages in those applications as part of a search of Mr. Mootoo’s phone incident to arrest. He did not need to open, read or screenshot the messages to prevent the loss of relevant evidence. And Det. Braganza testified that his investigation would not have been stymied or hampered if he had not reviewed the messages that night. Once the passwords were changed, a warrant should have been obtained before the contents of the Mr. Mootoo’s BBM, Kik and Instagram accounts were searched and Mr. Mootoo’s privacy was further infringed.

[73] The Crown concedes there is no evidence or allegation that Mr. Mootoo ever communicated with H.J. through Snapchat or Plenty of Fish. Mr. Mootoo did not send H.J. any messages on Snapchat or Plenty of Fish while Det. Braganza was in possession of H.J.’s phone. Det. Braganza had no basis to search of those applications incident to Mr. Mootoo’s arrest.

[74] The Crown argued that by taking screenshots of the messages but not reading them, Det. Braganza was tailoring his search and minimizing the intrusion into Mr. Mootoo’s privacy. The Crown argued that Det. Braganza did not actually seize any information from Mr. Mootoo’s phone. He simply took steps to ensure a copy of the messages was saved on the phone and would be available when a warrant was later obtained. I disagree with this characterization of Det. Braganza’s search.

[75] First, I do not accept Det. Braganza’s evidence that he did not read any of the messages as he was taking the screenshots. Det. Braganza may not have read all of the messages in detail. But he opened each message and looked at them while taking the screenshots. This was an unnecessary intrusion into Mr. Mootoo’s privacy. The accounts had already been secured. Det. Braganza should have waited until a warrant was obtained to look at any of the messages.

[76] Second, Det. Braganza admitted that he indiscriminately captured every message in every Internet-based messaging application on Mr. Mootoo’s phone. Det. Braganza did not know if there were any messages in Kik, Snapchat, Instagram or Plenty of Fish between H.J. and Mr. Mootoo when he opened those applications and started taking screenshots. There was no basis to think there would be any relevant evidence in the Kik or Snapchat applications. This is the opposite of a tailored search. The common law power to search incident to arrest is an extraordinary power. The police are required to strictly respect the limits of their authority: Fearon, at para. 16. The police must carefully consider what needs to be done promptly to avoid the loss or destruction of evidence and take steps to avoid any unauthorized invasion of the suspect’s privacy: Fearon, at paras. 74 and 75.

[77] Det. Braganza did not limit his search of Mr. Mootoo’s phone to those applications and those messages that were relevant to his investigation. Nor did he consider what steps were truly necessary to preserve relevant evidence on the phone. Det. Braganza’s searches of Mr. Mootoo’s cell phone went well beyond what was authorized under the common law power to search incident to arrest.

(c) Did the police adequately document their search of Mr. Mootoo’s phone?

[78] For a cell phone search incident to arrest to be valid, the police must record the applications searched, the extent of the search, the time of the search, and the search’s purpose and duration: Fearon, at para. 82. In other words, the police must keep notes to explain what they searched and why: R. v. Caslake, 1998 CanLII 838 (SCC), [1998] 1 SCR 51, at p. 66. Having a clear record of what the police did and why ensures the Court can effectively review the validity of the warrantless search incident to arrest after the fact: Fearon, at para. 70.

[79] Det. Braganza took some notes of his search of Mr. Mootoo’s phone. He noted the changes he made to some of Mr. Mootoo’s accounts. He also made notes of the approximate times he was searching Mr. Mootoo’s phone. But Det. Braganza did not take detailed notes as the Supreme Court directed in Fearon.

[80] It became clear during cross-examination that Det. Braganza could not remember exactly what he did during the search of Mr. Mootoo’s phone. For example, he was asked if he took screenshots in BBM just from the day of Mr. Mootoo’s arrest or from other days as well. Det. Braganza testified he took screenshots of every message. He also testified that he “thinks” there were only messages from the day Mr. Mootoo was arrested but he was not sure. Det. Braganza also testified he could not remember if he changed the password or email address associated with Mr. Mootoo’s Plenty of Fish account. Det. Braganza testified that he thinks he changed the password for the BBM account but cannot be completely certain because he does not have a note of the new password he entered.

[81] To the extent that Det. Braganza made notes of the timing of his searches, the times are estimates at best. For example, Det. Braganza testified he searched Instagram, Snapchat and BBM before he went to execute the search warrant at Mr. Mootoo’s apartment. Det. Braganza testified there were so many messages in Kik that he finished searching that application after they executed the warrant.

[82] Det. Braganza’s notes say that he was back at the police station after Mr. Mootoo’s arrest at 6:21 p.m. Det. Braganza testified that was just an estimate and he would have been back at the station sometime between 6:00 and 6:20 p.m. His notes also say he was at Mr. Mootoo’s apartment at 6:55 p.m. to execute a warrant. Det. Braganza testified it took him approximately 15 minutes to drive to Mr. Mootoo’s apartment, which means he spent somewhere between 20 and 40 minutes searching Mr. Mootoo’s phone before he left to execute the warrant. His notes suggest he resumed the search of Mr. Mootoo’s phone at 9:10 p.m. At 9:44 p.m., Det. Braganza started his interview with Mr. Mootoo. Det. Braganza could not say how much time between 9:10 and 9:44 p.m. he spent searching Mr. Mootoo’s phone.

[83] While Det. Braganza’s notes offer a general idea of how long he spent searching Mr. Mootoo’s phone, he did not record which applications he accessed, when he accessed each application, in what order he accessed the applications, how long he spent searching each application, or what exactly he did and saw when he opened each application. As a result, I am left to rely on his testimony, which I have found to be not credible at times, and his imperfect memory. This is not acceptable. Cell phones can store a massive amount of personal information. The search of any phone incident to arrest has the potential to be a profound invasion of privacy. Det. Braganza had an obligation to make detailed notes so the scope of his search was clear and the validity of his search can be effectively reviewed. He failed to do so.

[84] Had Det. Braganza made detailed notes of his search, he might have realized that a search of every message in every messaging application was not necessary to preserve relevant evidence and was not authorized in this case. As the Supreme Court noted in Fearon, at para. 82, the constitutional requirement for officers to take detailed notes of a cell phone search can focus the officer’s attention on whether the search meets all the requirements of a lawful search incident to arrest.

[85] I find that the search of Mr. Mootoo’s phone incident to arrest was unreasonable.

D. Warranted Search of Mr. Mootoo’s phone

[86] On April 26, 2017, the police obtained a warrant to examine the content of the phone seized from Mr. Mootoo during his arrest. Mr. Mootoo argued that the warrant filed as an exhibit was a forgery. Relying on Det. Braganza’s testimony at the preliminary inquiry, Mr. Mootoo argued the police never obtained a warrant to search his phone. I have already rejected Det. Braganza’s preliminary inquiry testimony on this point. Det. Braganza lied when he said no warrant had been obtained for Mr. Mootoo’s phone.

[87] I am satisfied that Det. Garrity applied for and obtained a warrant to search Mr. Mootoo’s phone in April 2017. Det. Garrity testified that he submitted two applications for a warrant to search Mr. Mootoo’s phone. The first application was rejected because it contained an error. He testified that the second application was granted on April 26, 2017. Det. Garrity testified that he took Mr. Mootoo’s phone and the warrant to the Tech Crimes Unit after the warrant was issued. I accept Det. Garrity’s evidence on these points.

[88] I am also satisfied that the phone analyzed by Det. Garcia on May 8, 2017 was the phone seized from Mr. Mootoo.

[89] Amicus argued that even if the warrant to search Mr. Mootoo’s phone was valid, the search itself was unreasonable because information was downloaded from Mr. Mootoo’s phone that was not authorized by the warrant. In particular, Det. Garcia downloaded Mr. Mootoo’s web-browsing history when he analyzed the phone.

[90] The warrant authorized a search of Mr. Mootoo’s phone for the following:

i. Call log information (received, dialed and missed);

ii. Text messaging and App [application] messaging information (received, sent and missed);

iii. Internet calls and email information (received, dialed and missed); and

iv. Photograph and video information in any electronic format stored on the cell phone and SIM card.

[91] Det. Garcia testified he reviewed the warrant before he extracted data from Mr. Mootoo’s phone. Det. Garcia used a forensic tool that allowed him to exclude categories of data from the extraction process. Det. Garcia excluded several categories of data based on the scope of the warrant. He excluded audio files, notes, memos or calendar entries. He also excluded geo-location data.

[92] Det. Garcia extracted the web-browsing history from Mr. Mootoo’s phone even though it was not expressly authorized in the warrant. He testified that the first item listed, “call log information”, was broad enough to include information about calls made or received using a Voice over Internet Protocol (or VoIP). He, therefore, thought that “internet calls” in the third item would be redundant unless it meant something other than calls using a VoIP. To avoid any redundancy, he interpreted “internet calls” to mean Internet activity and included web-browsing history in the extraction report.

[93] I do not agree with Det. Garcia’s interpretation of the warrant. Even if there is some potential redundancy, the term “internet calls” is not ambiguous. In my view, “call log information” was intended to capture information about traditional telephone calls made, received or missed on Mr. Mootoo’s phone. “Internet calls” was intended to capture information about voice calls using a VoIP or other Internet based applications. I find that the warrant did not authorize Det. Garcia to search the web-browsing history on Mr. Mootoo’s phone and the seizure of the web-browsing history violated his rights under s. 8 of the Charter.

E. Search of Mr. Mootoo’s apartment

[94] After Mr. Mootoo’s arrest, the police executed a search warrant at his apartment. The warrant authorized the police to search for a black hat with gold lettering; black and grey shoes; baggy, dark-coloured pants; identifying documentation; and electronic devices. The warrant also authorized the examination of any electronic devices seized from the apartment for messaging application files associated with the name Jay or one of Jay’s online profiles.

[95] Amicus argued the search of Mr. Mootoo’s apartment was unreasonable because the police seized items that were not listed in the warrant.

[96] The police did seize items that were not listed in the warrant. I find those items were in plain view during the search and the police were authorized to seize them. The plain view doctrine requires that the police have prior justification to search the place where they found the other item seized in “plain view” occurred: Buhay, at para. 37. Here, the police had a valid warrant to search Mr. Mootoo’s apartment for various pieces of clothing, electronics and identification.

[97] In addition to the items listed in the warrant, the police seized a second hat that was on the sofa in the apartment and a second pair of shoes from the mat in the hall. Before executing the warrant, Det. Braganza watched surveillance video from Cedarbrae Mall that showed H.J. and the person she identified as Jay on the morning of March 24, 2017. H.J. told Det. Braganza she and Jay went to Tim Hortons to get something to eat after they woke up on March 24, 2018. Det. Braganza testified they seized any item of clothing they thought might match the clothing worn by the person with H.J. in the video.

[98] The police also seized a large glass canister with a metal lid from Mr. Mootoo’s bedroom. During her police statement, H.J. told Det. Braganza that Jay had a glass canister filled with marijuana in his room when she was at his apartment. Det. Braganza testified that he seized the canister because it was consistent with H.J.’s description of the canister she saw in Jay’s room and could corroborate her statement.

[99] The police seized an imitation firearm that was in the dresser in Mr. Mootoo’s bedroom and a security vest that was hanging in Mr. Mootoo’s closet. Det. Braganza agreed they seized items that were not included in the warrant. He testified that he thought he was authorized to seize any item in plain view during the search.

[100] The officers were entitled to search Mr. Mootoo’s bedroom and the living room for the items in the warrant. They were also entitled to seize any other items they saw in plain view if they had reasonable grounds to believe those items might afford evidence of the offences under investigation or were otherwise illegal. I find that the seizure of the additional items of clothing, the imitation firearm and the glass canister was justified under the plain view doctrine and does not render the search of Mr. Mootoo’s apartment unreasonable. The evidence seized from Mr. Mootoo’s apartment is, therefore, admissible.

F. Exclusion of the Evidence

[101] I have found that the messages sent by Mr. Mootoo and captured during the undercover investigation were obtained in violation of his Charter rights. I have also found that the screenshots taken during the search of Mr. Mootoo’s phone incident to his arrest were obtained in violation of his rights. Finally, I have found that the seizure of the web-browsing history during the forensic analysis of Mr. Mootoo’s phone violated his rights.

[102] Evidence obtained in a manner that violates the Charter must be excluded if the admission of the evidence would bring the administration of justice into disrepute: Charter, s. 24(2). When deciding whether the admission of evidence would bring the administration of justice into disrepute, I must consider and balance three factors: the seriousness of the Charter-infringing state conduct, the impact of the breaches on Mr. Mootoo’s Charter-protected rights, and society’s interest in the adjudication of this case on its merits: R. v. Grant, 2009 SCC 32, [2009] 2 S.C.R. 353, at para. 71.

(a) Seriousness of the Charter-infringing state conduct

[103] The focus here is on the gravity of the police conduct that resulted in the violations of Mr. Mootoo’s Charter rights. Charter violations that are the result of willful or reckless disregard for the rights of an accused person are particularly serious and pose a greater risk of bringing the administration of justice into disrepute. On the other hand, the admission of evidence obtained through a minor or inadvertent Charter breach may not undermine public confidence in the administration of justice: Grant, at paras. 72-75.

[104] Regarding the use of H.J.’s phone to communicate with and intercept messages from Mr. Mootoo without a warrant, I find that Det. Braganza’s conduct falls towards the serious end of the spectrum. To be clear, I do not think Det. Braganza was acting in bad faith or deliberately disregarded Mr. Mootoo’s rights when he used H.J.’s phone to surreptitiously communicate with Mr. Mootoo. I accept Det. Braganza thought he was entitled to conduct the undercover investigation. He testified that he spoke to a senior officer from the Intelligence Covert Operations Unit about his plan to impersonate H.J. Det. Braganza testified that the senior officer told him that because he had completed training on Internet-facilitated investigations, he could use H.J.’s accounts.

[105] What makes this breach serious though is that Det. Braganza did not turn his mind to Mr. Mootoo’s privacy rights. Det. Braganza testified that once H.J. signed the consent permitting him to take over her accounts, he did not think about seeking a warrant. He thought that H.J.’s consent was all the authorization he needed to communicate with Mr. Mootoo and seize his messages. Det. Braganza testified that the nature of the relationship between H.J. and Mr. Mootoo did not factor into his consideration. He testified that even if H.J. were Mr. Mootoo’s girlfriend, he would have approached the investigation in the same manner. He still would not have sought prior judicial authorization to intercept his messages. Det. Braganza recognized that H.J. had a privacy interest in the content of the messages but did not turn his mind to any corresponding privacy interest that Mr. Mootoo had in those messages.

[106] I appreciate that the seizure of digital communications is a complex area of law, and one which was evolving in 2017. Nonetheless, when there is uncertainty in the law, the police are expected to err on the side of caution “by choosing a course of action that is more respectful of the accused’s potential privacy rights”: Fearon, at para. 94. Det. Braganza’s failure to even consider whether Mr. Mootoo had a privacy interest in the messages that might be generated during the undercover investigation makes this breach more serious.

[107] The search of Mr. Mootoo’s cell phone incident to arrest is a particularly serious violation of Mr. Mootoo’s Charter rights. The search went far beyond what was authorized. The Supreme Court of Canada articulated the four requirements for a valid cell phone search incident to arrest in Fearon in 2014, four years before the search of Mr. Mootoo’s phone. In Fearon, the Supreme Court was clear that only cursory, tailored searches of cell phones are permitted incident to an arrest. And the search must be documented in detail. By April 2017, Det. Braganza had completed all five levels of the Internet Facilitated Investigations course offered by the Toronto Police Service. He, therefore, knew or should have known the requirements for a search of a cell phone incident to arrest. Despite his training, his search was much broader than authorized and he failed to clearly document his search. This, in my view, shows a clear disregard by Det. Braganza for Mr. Mootoo’s Charter rights or an unacceptable lack of understanding of Mr. Mootoo’s rights.

[108] The breaches of Mr. Mootoo’s privacy rights during the undercover investigation and the search of his cell phone incident to his arrest are made even more serious by the fact that they are part of a broader pattern of conduct that demonstrates an ongoing disregard for Mr. Mootoo’s rights. In a separate ruling, I found that the police also violated Mr. Mootoo’s rights under ss. 10(a) and 10(b) of the Charter: R. v. Mootoo, 2021 ONSC 2596. I found that the police did not properly advise Mr. Mootoo of the reasons for his arrest. The police also failed to give Mr. Mootoo an opportunity to exercise his right to counsel at the first opportunity. They waited almost two hours to facilitate Mr. Mootoo’s right to counsel. Mr. Mootoo’s arrest was carefully planned. But no plan was made to ensure that his right to counsel would be facilitated immediately. Moreover, none of the officers involved in Mr. Mootoo’s arrest thought it was their responsibility to put him in touch with counsel.

[109] I have also found that the officer in charge of this investigation, Det. Braganza, lied to the Court at Mr. Mootoo’s preliminary inquiry about whether a warrant had been obtained to search his phone. While not part of the Charter breaches themselves, Det. Braganza’s dishonesty is relevant to my assessment of the seriousness of the police conduct in this case: R. v. Harrison, 2009 SCC 34 at para. 26.

[110] The investigation and arrest of Mr. Mootoo is marked by a pattern of general disregard for his Charter rights. While the Charter violations may not have been deliberate, the pattern of indifference makes the police conduct serious. This favours the exclusion of the evidence generated during the undercover investigation and the search of Mr. Mootoo’s phone incident to arrest. Admitting evidence obtained in circumstances where there is a pattern of indifference towards a suspect’s Charter rights tends to bring the administration of justice into disrepute: R. v. Adler, 2020 ONCA 246 at paras. 41-44.

[111] The police conduct that led to the breach of Mr. Mootoo’s rights during the search of his phone after a warrant was obtained was much more minor. The police obtained a warrant. Det. Garcia reviewed the warrant before he extracted information from Mr. Mootoo’s phone. He excluded many categories of information from his search in accordance with the warrant. And most of the information he seized from Mr. Mootoo’s phone was authorized by the warrant. He included one category of information – web-browsing history – that was not authorized by the warrant. Det. Garcia explained he thought there was some inconsistency or ambiguity in the warrant and interpreted it in a manner that authorized the seizure of web-browsing history. I do not agree with his interpretation of the warrant. While there may have been some redundancy in the list of information to be seized, there was no ambiguity about what was authorized. Nonetheless, it is clear that Det. Garcia was trying to respect Mr. Mootoo’s rights and to not exceed the scope of the warrant.

(b) Impact of the Breaches on Mr. Mootoo’s Charter-Protected Interest

[112] The impact of Charter breaches can range from fleeting or technical, on one end of the spectrum, to profound on the other end: Grant at para. 76.

[113] I find the undercover operation had a profound impact on Mr. Mootoo’s privacy rights. The police effectively conscripted Mr. Mootoo to create evidence against himself. This case is not like cases where a complainant turns over existing communications to the police: see for example R. v. Phagura, 2019 BCSC 1638. In those cases, the police are passive recipients of messages that already exist. Here, the officer was eliciting evidence from Mr. Mootoo to be used against him.

[114] The undercover operation was not a fleeting invasion of Mr. Mootoo’s privacy either. Text communications are among the most private forms of communication possible. Det. Braganza exchanged hundreds of messages with Mr. Mootoo over almost three weeks. This was a profound invasion of Mr. Mootoo’s privacy.

[115] The unreasonable search of Mr. Mootoo’s phone incident to arrest also had a profound impact on Mr. Mootoo’s privacy. Det. Braganza searched every messaging application on Mr. Mootoo’s phone. He took screenshots of hundreds of messages that have no apparent connection to the investigation of the offences involving H.J. Det. Braganza indiscriminately opened, captured and copied every message in every application. Because of the amount of personal information that can be stored on a cell phone, any search of any cell phone has the potential to be a very significant invasion of a person’s privacy interest: Fearon at para. 96. While Det. Braganza did not search all of the contents of Mr. Mootoo’s phone, the search incident to arrest was extensive. Det. Braganza spent hours looking through and copying hundreds of messages without authority to do so.

[116] The impact of these breaches of Mr. Mootoo’s Charter rights favours the exclusion of the evidence obtained during the undercover operation and during the search of his phone incident to arrest.

[117] The impact of the breach of Mr. Mootoo’s Charter rights during Det. Garcia’s search of his phone after the warrant was obtained is also quite serious. Web-browsing history provides a roadmap to a user’s online activities. It reveals an enormous amount of information that goes to the biographical core of who we are. It can disclose our interests, preferences and propensities. It records what we search, what we read and what we watch online: R. v. Morelli, 2010 SCC 8, [2010] 1 S.C.R. 253, at paras. 3 and 105. The forensic tool used by Det. Garcia also captured, as part of the web-browsing history, any documents downloaded from the Internet onto the phone.

[118] In this case the impact of the breach was mitigated to some extent by the fact that neither Det. Garcia nor Det. Braganza reviewed the web-browsing history. Det. Garcia testified that the extraction report from Mr. Mootoo’s phone was more than 2000 pages long. He testified that he only reviewed the photographs, call logs and chat logs extracted from Mr. Mootoo’s phone. He testified that none of the other parts of the extraction report were relevant to his investigation and he did not review them. Nonetheless, the potential impact of this breach on Mr. Mootoo’s privacy rights was significant and tends to favour the exclusion of his web-browsing history.

(c) Society’s Interest in the Adjudication of the Case on its Merits

[119] The third line of inquiry under s. 24(2) of the Charter asks whether admitting or excluding the evidence better serves the truth-seeking function of a criminal trial. To answer this question, the Court will consider the reliability of the evidence and the importance of the evidence to the Crown’s case. The exclusion of reliable evidence could undermine the truth-seeking function of a criminal trial and bring the administration of justice into disrepute. Similarly, the exclusion of evidence that is crucial to the Crown’s case could bring the administration of justice into disrepute: Grant at paras. 79-83.

[120] The Court can also consider the seriousness of the charges, but this factor cuts both ways. On the one hand, the public has a heightened interest in seeing serious charges resolved on their merits. On the other hand, the public has an interest in ensuring that police investigate serious offences in a Charter-compliant manner, because the stakes are so high for the accused: Grant, at para. 84. The charges against Mr. Mootoo are extremely serious. He is charged with several sexual offences involving a 15-year-old girl. Society has a very strong interest in a resolution of this case on its merits. But society also has a strong interest in ensuring the police respect Charter rights during their investigations of serious offences.

[121] The evidence obtained in violation of Mr. Mootoo’s Charter rights is reliable. The screenshots of messages sent to H.J.’s BBM account and the screenshots of messages in the various applications on Mr. Mootoo’s phone are accurate pictures of the data on Mr. Mootoo’s phone. The forensic analysis of Mr. Mootoo’s phone was done using a tool that reliably extracts information without altering it in any way. Mr. Mootoo has raised some potential issues about the reliability of this evidence. For example, the messages captured by Det. Braganza during the undercover investigation, which the Crown says were sent by Mr. Mootoo, originated from a BBM account with the username “Knight in Shining Armour.” H.J. told the police that “Knight in Shining Armour” was the account she used to communicate with Jay. Mr. Mootoo denies he is Jay. Mr. Mootoo denies the phone searched by Det. Garcia is his phone. And Mr. Mootoo denies that “Knight in Shining Armour” is his BBM account. While the Crown will have to prove that Mr. Mootoo was the person sending messages from the “Knight in Shining Armour” BBM account, that does not detract from the reliability of the evidence for the purpose of assessing whether it should be admitted under s. 24(2).

[122] The messages seized during the undercover operation and messages captured during the search of Mr. Mootoo’s phone incident to arrest are important evidence in the Crown’s case. They provide direct evidence of the actus reus of some of the charges Mr. Mootoo is facing. They are also relevant to the issue of identity. However, excluding the messages will not undermine the Crown’s case to the point that the Crown will be unable to proceed on any of the charges. I have not been made aware of any relevant or inculpatory evidence in Mr. Mootoo’s web-browsing history.

F. Conclusion

[123] When the seriousness of the Charter-infringing conduct and the impact of the Charter-infringing conduct favour the exclusion of evidence, the third line of inquiry will seldom, if ever, tip the balance in favour of admitting evidence obtained in violation of a defendant’s Charter rights: R. v. McGuffie, 2016 ONCA 365, 131 O.R. (3d) 643, at para. 63. Here, the first two lines of inquiry strongly support the exclusion of the evidence obtained during the undercover investigation and the search of Mr. Mootoo’s phone incident to arrest. The third line of inquiry cannot tip the balance in favour of admitting the evidence, notwithstanding the seriousness of the charges and the importance of the evidence to the Crown’s case.

[124] The first line of inquiry favours the admission of the web-browsing history seized in violation of Mr. Mootoo’s rights during the search of his phone after the warrant was obtained. The second line of inquiry tends to favour the exclusion of the web-browsing history because of the impact on Mr. Mootoo’s privacy interests. The third line of inquiry clearly supports the admission of that evidence. On balance, I find the administration of justice would not be brought into disrepute by the admission of the results of the warranted search of Mr. Mootoo’s phone.

[125] I, therefore, find that the evidence obtained while the police were impersonating H.J. and using her phone to communicate with Mr. Mootoo is inadmissible. The evidence obtained from the search of Mr. Mootoo’s phone incident to arrest is also inadmissible. The results of the search of Mr. Mootoo’s phone after the warrant was obtained are admissible.

Davies J.

Written Reasons Released: January 18, 2022

Edited Written Reasons Released: January 24, 2022