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The Defence Toolkit – March 29, 2025: Breaches and Discoverability

Amicus | Charter s24(2) | Discoverability | Overturning a Guilty Plea

Posted On 29 March 2025

This week’s top three summaries: R v James, 2025 ONCA 213: s24(2) #discoverability, R v Gordon, 2025 ONCA 201, judge #promise and GP, R v JC, 2025 ONCA 230: expanded #amicus

R v James, 2025 ONCA 213

[March 20, 2025] Charter s.24(2): Discoverability and Cumulative Effect of Breaches [Reasons by van Rensburg J.A. with B.W. Miller and S. Gomery JJ.A concurring] 

AUTHOR’S NOTE: Discoverability of evidence plays a crucial role in the second stage of the Charter s.24(2) analysis. It can either mitigate or aggravate the seriousness of a Charter breach:

  • If the evidence would have been discovered lawfully, the breach may seem technical, reducing its impact.

  • However, if police could have obtained the evidence lawfully but chose not to, this aggravates the violation.

In this case, the trial judge relied too heavily on discoverability to justify admitting evidence, failing to account for the cumulative impact of multiple Charter breaches. The Court of Appeal intervened, reassessed s.24(2), and excluded the evidence due to the Charter violations of s.10(b) and s.8.

[1] The appellant was charged with trafficking crack cocaine and possessing fentanyl and crack cocaine for the purpose of trafficking following his arrest at a convenience store in downtown Toronto. At trial, he brought a Charter application alleging breaches of ss. 8, 9 and 10(b), and seeking under s. 24(2) to exclude evidence: crack cocaine that was seized at the store when he was arrested, scales and money found in the search of his vehicle, and fentanyl and crack cocaine that were removed from his pants when he arrived at the police station.

[2] The trial judge found that the police had breached certain of the appellant’s Charter rights. He concluded that the appellant’s arrest and search incident to the arrest did not contravene the Charter, but that the search of his motor vehicle contravened s. 8, and that the police violated s. 10(b) when they spoke with him and searched him after he had indicated he wanted to speak with counsel but before he was afforded the opportunity to do so. Only the fruits of the motor vehicle search were excluded from evidence at trial. While the trial judge was very critical of the police officers’ conduct, and he held that the first Grant factor pulled heavily in favour of exclusion, he ultimately admitted in evidence the drugs found in the appellant’s pants.

[3] With the admission of this evidence and the trial judge’s acceptance of the testimony of the arresting officers that they had seen the appellant transfer a small amount of crack cocaine by placing it on a shelf in the convenience store, the appellant was convicted of all three offences…

[4] The appellant appeals his convictions, submitting that the trial judge erred in failing to exclude from his trial the evidence of the drugs that were seized in violation of his s. 10(b) rights…

[5] For the reasons that follow, I would allow the appeal from the appellant’s convictions for possession for the purpose of trafficking fentanyl and crack cocaine, and, recognizing that the evidence of the drugs seized from the appellant was essential to the appellant’s convictions on these charges, I would substitute verdicts of acquittal…

[6] Briefly, with respect to the possession for the purpose of trafficking convictions, the trial judge erred in his Grant analysis when he decided not to exclude the drug evidence that was seized from the appellant on his arrival at the police station. In considering the first Grant factor, the trial judge did not give proper effect to his significant findings of police misconduct that demonstrated a serious disregard for the appellant’s Charter rights, and the officers’ dishonest and misleading evidence in court. In concluding that the second Grant factor favoured the admission of the evidence, the trial judge allowed the fact that the drugs would have been found in any event to overwhelm his analysis…

…the trial judge completed his analysis without conducting a final balancing to determine whether, considering all the circumstances, admission of the evidence would bring the administration of justice into disrepute. Conducting the Grant analysis anew, I would exclude the evidence of the drugs that were seized in violation of the appellant’s s. 10(b) rights.

B. THE CHARTER APPLICATION AND THE TRIAL JUDGE’S FINDINGS

[18] The trial judge was very critical of various aspects of the police officers’ evidence, concluding that several officers had lied under oath. The trial judge also concluded that the appellant had exaggerated his evidence with respect to his treatment by the police and that he was not entirely honest with the court.

[20] As for the alleged violation of s. 8 in the search of the appellant’s vehicle, the trial judge did not believe the arresting officers’ evidence that they conducted an “inventory search” to ensure that none of the appellant’s belongings went missing after someone told them the car would be towed. Rather, as P.C. Esteves eventually admitted, the purpose of the search was to see if there were more drugs or related evidence in the vehicle, and the police had no legal authority to search the vehicle. The Crown conceded that the search of the appellant’s car violated s. 8 and did not seek to lead any evidence resulting from that search. According to the trial judge, the evidence demonstrated a “rather cavalier attitude towards the [appellant’s] Charter rights”, and the seriousness of the breach was aggravated by the fact that the arresting officers were dishonest about the reason for the search.

[21] The trial judge concluded that the implementational components of the appellant’s rights under s. 10(b) were breached by P.C. Freeman’s conduct at the police station. D.C. Sukman had explained both the arrest and the appellant’s s. 10(b) rights when the appellant was taken to the police vehicle. While the arresting officers could not recall any such conversation, the trial judge accepted the appellant’s evidence that he had asserted his s. 10(b) rights by asking to speak with a lawyer when he was still in the convenience store. The trial judge concluded that neither of the arresting officers had advised the transporting officers about the appellant having asserted his right to counsel prior to his transport to the station, and that P.C. Freeman had not, in turn, asked the transporting officers about the appellant’s right to counsel. He found that the appellant’s rights under s. 10(b) were violated when, before he had the opportunity to speak to counsel, and without asking him whether he wished to speak to counsel, he was questioned and searched, and fentanyl and crack cocaine were retrieved from his pants.

[22] The trial judge found that P.C. Freeman was a dishonest witness overall when he testified about his interactions with the appellant. He referred to the sally port entrance video evidence that captured the officer’s “aggressive” and “animated” manner of speaking with the appellant. He rejected the officer’s testimony that he had asked that the in-car camera be shut off for investigative purposes in order to protect the appellant, who he thought was going to try to provide police with sensitive information. The trial judge found that the officer was dishonest when he initially denied (but eventually admitted to) asking the appellant whether he had drugs on him. He found that the officer lied when he claimed he could not remember who removed the drugs from the appellant’s pants and when, after conceding he might have taken the fentanyl out of the back of the appellant’s pants, he insisted that he had not removed the crack cocaine.

[23] The trial judge also criticized the transporting officers’ evidence that, although they were close enough to see and hear what was going on, they did not remember the interaction between the appellant and P.C. Freeman after the in-car camera was turned off. He characterized their evidence as at best a “failure to take proper notes and a failure of memory” and at worst as “not being honest with the Court”.

[26] With respect to the s. 10(b) breach, the trial judge concluded that the conduct outside the sally port, both in questioning and searching the appellant, constituted a serious violation of his s. 10(b) rights and that the officer had acted in reckless disregard of these important rights. He concluded that the first prong of the Grant test strongly favoured the exclusion of the drugs seized by the officer.

28] With respect to the s. 10(b) violation, after stating that the violation was serious because the implementational duties imposed by the Charter-protected right to counsel had been ignored, the trial judge noted that the drugs would have been discovered once the appellant was subjected to a Level 3 search after he was booked, regardless of the breach. As such, he observed that the practical effect of the s. 10(b) breach was that the drugs were discovered and seized slightly earlier than they otherwise would have been. The trial judge concluded that this branch of the analysis supported the inclusion of the evidence seized from the appellant in the sally port area.

[30] The trial judge concluded his analysis by stating that he would exclude from the trial the products of the search of the appellant’s vehicle, and that he would not exclude the drugs seized by P.C. Freeman.

D. DISCUSSION

(1) THE CHARTER GROUND OF APPEAL

(a) Standard of review

[34] On an appeal of a s. 24(2) decision, a trial judge’s assessment of the Grant factors in light of the facts is typically entitled to deference. A s. 24(2) decision is reversible only when there is an error in legal principle, a palpable and overriding factual error, or an unreasonable determination: R. v. Truong, 2025 ONCA 69, at para. 37.

b) The first Grant factor

(i) The trial judge erred in compartmentalizing his assessment of the Charter breaches under s. 24(2)

[36] The appellant alleges that the trial judge adopted a compartmentalized approach to the Charter breaches, and that he failed to take into consideration the pattern of Charter-infringing conduct by the police. As a result, although the trial judge concluded that the first Grant factor weighed in favour of exclusion of both the evidence found in the search of the appellant’s vehicle and in the search of the appellant outside the sally port of the police station, the trial judge underestimated the seriousness of the police misconduct, and accordingly the strength of the first Grant factor in the overall analysis.

[37] As this court noted in Truong, a failure to consider related breaches together can distort the view taken of the seriousness of the Charter-offending conduct, and it may fail to capture the overall impact of the offending conduct on the accused’s Charter-protected interests, since they are all “part of the constellation of factors” relevant to this question: at para. 42, citing R. v. Mhlongo, 2017 ONCA 562, 355 C.C.C. (3d) 1, at paras. 60-62; R. v. Just, 2020 ONCA 362, 388 C.C.C. (3d) 273, at paras. 38 and 54; R. v. Zacharias, 2023 SCC 30, 487 D.L.R. (4th) 571, at para. 49.

[38] I agree with the appellant that the trial judge, in conducting his s. 24(2) analysis, adopted a compartmentalized approach to the Charter breaches. For each breach, he concluded separately that the police misconduct was serious. With respect to the s. 8 breach, he made an express finding of bad faith, which he said strongly favoured the exclusion of the evidence from the appellant’s car. With respect to the s. 10(b) breach, the trial judge concluded that P.C. Freeman, both in his questioning and search of the appellant, acted in reckless disregard of the appellant’s rights, which strongly favoured exclusion of the drugs.

[41] While the trial judge did not accept the argument at first instance that the breaches were consistent with other breaches by officers at 51 Division, and accordingly were systemic, he found multiple breaches in the specific dealings with the appellant, with officers showing a “cavalier attitude” and a “reckless disregard for” the appellant’s Charter rights. The fact that the appellant initiated the contact with P.C. Freeman does not justify or explain the officer’s failure to “hold off”, which was the breach of the s. 10(b) implementational duty, nor does it in any way attenuate the seriousness of the Charter-breaching conduct: an officer who, up to that point had no involvement in the police investigation or the appellant’s arrest, and who did not know whether the appellant had spoken with legal counsel, asked the appellant whether he had any drugs on him and then searched him by reaching into his pants.

42] By dealing separately with the s. 8 breach in the search of the vehicle and with the s. 10(b) breach in the search of the appellant outside the sally port, the trial judge did not give effect to the fact that the multiple breaches demonstrated a pattern of police disregard for the appellant’s rights.

(ii) The trial judge erred in failing to consider the impact of the police officers’ dishonesty

[44] Police dishonesty aggravates the seriousness of a Charter breach and is properly considered in relation to the first Grant factor given the need for a court to dissociate itself from such behaviour: R. v. Harrison, 2009 SCC 34, [2009] 2 S.C.R. 494, at para. 26. The failure to consider police dishonesty or understating its impact in the s. 24(2) assessment is an error: R. v. Lai, 2019 ONCA 420, at paras. 13-23; R. v. Pino, 2016 ONCA 389, 130 O.R. (3d) 561, at paras. 100-103.

[45] That error was made by the trial judge in this case. Although the trial judge made findings that certain officers had lied under oath, and accordingly rejected aspects of their evidence in finding s. 8 and s. 10(b) breaches, he did not refer to these findings in his assessment of the first Grant factor.

(iii) Conclusion on the trial judge’s assessment of the first Grant factor

[47] Even if the trial judge concluded that the police misconduct in relation to the s. 10(b) breach was very serious and “strongly favoured” the exclusion of the drugs seized from the appellant outside the sally port, in adopting a compartmentalized approach to the breaches that ignored the pattern of police misconduct and in failing to advert to the police dishonesty when officers gave their evidence in court, the trial judge underestimated the seriousness of the state misconduct and the extent to which the first Grant factor alone weighed in favour of exclusion of the evidence.

(c) The second Grant factor

[51] I begin by referring to the specific s. 10(b) breach that the trial judge found in this case. Here, the breach was in an officer’s failure to “hold off” after the appellant had expressed a desire to speak to counsel. This duty requires the police to promptly facilitate access to legal advice and, in the interim, to refrain from taking further investigative steps to elicit evidence from the detainee until the requested access to counsel has been provided: R. v. Burnett, 2021 ONCA 856, 159 O.R. (3d) 321, at paras. 131, 135; R. v. Willier, 2010 SCC 37, [2010] 2 S.C.R. 429, at para. 33.

[52] I agree that the trial judge did not give sufficient consideration to all of the circumstances related to the second Grant factor. He stated only that the violation was “serious in so far as it involved the officer ignoring the implementational duties imposed on police by s. 10(b)”, and that the actions had no effect on when the appellant was permitted to speak to his lawyer. In considering the second Grant factor, the trial judge emphasized one point: that the “practical effect” was that the drugs were seized slightly earlier than they would have been. In other words, the drugs were discoverable irrespective of the Charter breach.

[53] In considering the second Grant factor the court must “look to the interests engaged by the infringed right and examine the degree to which the violation impacted on those interests”: Grant, at para. 77. In the second Grant factor analysis, multiple breaches should be considered as part of “all the circumstances” considered under s. 24(2): Zacharias, at paras. 55-57. The fact that evidence would have been discovered in the police investigation without the Charter breach is relevant to the second Grant factor, but not determinative: R. v. Côté, 2011 SCC 46, [2011] 3 S.C.R. 215, at para. 70; Grant, at para. 122; Rover, at para. 43.

[54] While discoverability of the evidence is a factor appropriately considered at the second stage of the Grant analysis, in this case the trial judge allowed this factor to dominate when he concluded that the second Grant factor supported the inclusion of the evidence at the trial. The trial judge did not address how the failure to “hold off” (which was the essence of the s. 10(b) breach in this case) affected the specific interests of the appellant: his right against self-incrimination and his personal integrity. Unlike many s. 10(b) cases, the impact on the appellant in this case was not in the delay in his ability to speak to counsel – with the various benefits that speaking with counsel could have offered. The fact that a statement was elicited, and an intrusive search was conducted, ought to have been taken into consideration in weighing the second Grant factor.

[55] As in R. v. Jarrett, 2021 ONCA 758, 498 C.R.R. (2d) 38, the trial judge failed to consider all of the interests the appellant’s right to counsel is to protect in his evaluation of the impact of the s. 10(b) breach, and he placed undue emphasis on the lack of a causal connection between the search and seizure of the evidence and the breach, in concluding that the search and seizure would have happened anyway: at paras. 51, 55; see also R. v. Whittaker, 2024 ONCA 182, 435 C.C.C. (3d) 221, at para. 53. [Emphasis by PJM]

[56] Nor did the trial judge consider the cumulative effect of theCharter breaches on the appellant at the second stage of his Grant analysis. Rather, he considered the impact of the s. 10(b) breach separately from the impact of the s. 8 breach, in respect of which the trial judge had concluded that the search “completely undermined [the appellant’s] privacy interests in the contents of the vehicle”…

(d) The third Grant factor

[57] No issue is taken with the trial judge’s consideration of the third Grant factor…

(e) The failure to conduct a final balancing

[58] Finally, the appellant asserts that the trial judge erred by not conducting a final balancing after considering each Grant factor. The appellant asserts that a proper balancing would have recognized that the first and second branches together made a very strong case in favour of exclusion.

[60] Although the trial judge adverted to the need to balance the assessments under the three lines of inquiry to determine whether, considering all the evidence, admission of the evidence would bring the administration of justice into disrepute, he did not conduct a final balancing. Instead, after addressing each of the Grant factors he concluded:

For the foregoing reasons, given the gravity of the violation of [the appellant’s] s. 8 rights arising from the search of the vehicle, I would exclude the products of that search from the trial. As for the drugs seized by P.C. Freeman, while this involves a breach of [the appellant’s] s. 10(b) rights, I would not exclude them from the trial.

[61] A final balancing was essential in this case. Where police misconduct is deliberate, rather than careless or negligent, and where the police give misleading or false evidence, it is particularly important for the court to consider and to weigh in the balance against the truth-seeking interests of the criminal justice system, the need to dissociate the justice system from the police misconduct: see Grant, at para. 75; Harrison at paras. 39-40; Pino, at para. 103.

(f) The s. 24(2) analysis conducted afresh

[65] At the first stage of the Grant analysis, effect must be given to the trial judge’s strong findings of police misconduct and dishonesty. The police conduct in this case was egregious, in terms of the dealings of individual officers with the appellant at the time of his arrest and detention, and their efforts to recast what happened in their evidence at the voir dire, which can only be understood as an attempt to minimize their misconduct. Moreover, even without a finding of systemic misconduct, there was a pattern of disregard for Charterrights. The first Grant factor pulls very strongly in favour of exclusion of the drugs.

[66] The second Grant factor also pulls toward exclusion of the drugs seized outside the sally port from the evidence at trial, albeit not as strongly as the first factor. The s. 10(b) breach resulted in the appellant providing incriminating information: his admission that he had drugs on him, leading to an intrusive search. This was a continuation of theCharter-infringing conduct that occurred when the appellant’s car was searched without reasonable grounds. In effect, the arresting officers and P.C. Freeman demonstrated to the appellant that they were intent on securing evidence of his drug dealing without regard for his Charter rights. While the effect of the s. 10(b) breach was mitigated by the fact that the drugs would have been found irrespective of the breach, this factor alone would not justify admission of the drugs in the circumstances of this case. As Cromwell J. noted in Côté, at paras. 69-74, the fact that evidence is legally discoverable can cut both ways: while it can attenuate the effect on the detainee’s interests under the second Grant factor, it can also heighten the seriousness of the police misconduct in proceeding illegally when a legal avenue was available: see also R. v. Tsekouras, 2017 ONCA 290, 353 C.C.C. (3d) 349, at para. 112, leave to appeal refused, [2017] S.C.C.A. No. 225; see also R. v. S.S., 2023 ONCA 130, 422 C.C.C. (3d) 277, at para. 89. [Emphasis by PJM]

[67] …I acknowledge that there is a very real societal interest in an adjudication of the charges on the merits, and that the third Grant factor strongly favours the admission of the evidence…

[69] Here, the first Grant factor very strongly weighs in favour of exclusion of the evidence, while the second Grant factor also favours exclusion, but not as forcefully. Together, they make a compelling case for exclusion…

…conducting the final balancing, however, the seriousness of the offence cannot be the controlling consideration in the decision whether to exclude evidence: Harrison, at para. 40. I refer to the observations of Doherty J.A. in R. v. McGuffie, 2016 ONCA 365, 131 O.R. (3d) 643, at para. 63, that “if the first and second inquiries make a strong case for exclusion, the third inquiry will seldom, if ever, tip the balance in favour of admissibility”…

[72] The effect of the exclusion of the evidence seized from the appellant outside the sally port area is to set aside the appellant’s convictions on counts 2 and 3, possession of cocaine and fentanyl for the purpose of trafficking, and to acquit him of these charges.

R v Gordon, 2025 ONCA 201

[March 14, 2025] Guilty Plea and Judicial Pre-Trial Promises [Reasons by Favreau J.A. with Janet Simmons and Gary Trotter JJ.A. concurring]

AUTHOR’S NOTE: This case highlights the risks of judicial pre-trial sentencing indications and the importance of a clear and specific guilty plea inquiry. The accused pleaded guilty based on a judge’s pre-trial comment suggesting a maximum 6-month sentence, only to receive a sentence five times longer. The Court of Appeal overturned the plea, emphasizing that if the accused had been specifically warned that the judge’s pre-trial indication was not binding, he may not have plead guilty.

This case raises concerns about the reliability of judicial sentencing indications in pre-trial conferences. While such indications can be valuable, appellate courts should establish clear rules to ensure they are meaningful and that accused persons do not plead guilty based on false expectations.

A. INTRODUCTION

[1] The appellant, Dwayne Gordon, pleaded guilty to five offences related to human trafficking:…

…The plea judge imposed a sentence of two-and-a-half years in addition to the time Mr. Gordon had already served while awaiting trial.

[2] Mr. Gordon seeks to set aside his guilty plea on the basis that it was uninformed.2 He claims that his lawyer assured him that the plea judge would only impose six months in custody in addition to the time he had already served.

[3] Based on the evidence filed on appeal, I am satisfied that the guilty plea should be set aside. Mr. Gordon’s evidence and his trial counsel’s evidence show that Mr. Gordon agreed to plead guilty because he understood that he would only have to serve an additional six months. Mr. Gordon’s evidence also demonstrates that he would not have pleaded guilty if he understood that he could serve an additional two-and-a-half years.

B. BACKGROUND

[6] Mr. Gordon was denied bail and was detained at the Toronto South and Toronto East Detention Centres while awaiting trial.

[8] Prior to trial, defence and Crown counsel attended a judicial pre-trial with Justice Bonnie L. Croll of the Superior Court of Justice. In that context, Mr. Gordon’s trial counsel shared information about lockdown days and conditions of incarceration, and continued to advocate for a guilty plea based on time served. The Crown rejected this position. Mr. Gordon was tentatively scheduled to plead guilty before Justice Croll, but he decided not to do so given that the Crown did not agree that time served would be an appropriate sentence.

[9] On November 21, 2022, the day the trial was scheduled to begin, counsel attended another judicial pre-trial, this time before the plea judge. The Crown’s position at that appearance was that a sentence in the range of 8 to 10 years would be appropriate. The evidence from Mr. Gordon’s trial counsel is that the plea judge said that “he may sentence Mr. Gordon to between six months and a year in custody beyond the time he already served in pre-trial custody”. Mr. Gordon’s trial counsel asked that the trial be put off for a day so that he could get instructions.

[10] Mr. Gordon did not agree to a plea deal that would involve additional time in custody of 6 to 12 months. He told his counsel that he would agree to plead guilty if he could be released from custody within three months.

[11] The following day, at the request of Mr. Gordon’s trial counsel, the plea judge held another judicial pre-trial. The evidence from Mr. Gordon’s trial counsel is that the plea judge rejected the suggestion of only an additional three months in custody but said that if Mr. Gordon pleaded guilty, he would sentence him to no more than a further six months in custody. Mr. Gordon’s trial counsel made a contemporaneous note of this discussion, in which he recorded the following:

The Crown and I had a further JPT with Justice Goldstein.

Per [Mr. Gordon], I pitched the three months further custody, instead of six, which he said he would take in a heartbeat.

Justice Goldstein was not having it, saying he is happy to resolve and give deals, but he was worried he’d be going too low so that it would be an unfit sentence.

I was told by Justice Goldstein, who had reviewed Justice Code’s decision3 that he thought six months was a good deal.

[The Crown] thought it was a really good deal too – in fact, she wasn’t really content with it, but she’d live with it.

Justice Goldstein said I could tell [Mr. Gordon] the reason he was getting such a good deal is he was sparing the complainant being subjected to lengthy crossexamination by counsel. [Emphasis added.]

[12] Crown counsel’s evidence is that the plea judge did not make a commitment to six months beyond the time Mr. Gordon had already served and that she maintained her position that a sentence of 8 to 10 years would be appropriate. Crown counsel did not make contemporaneous notes of this second judicial pretrial with the plea judge.

[13] Mr. Gordon agreed to plead guilty after his trial counsel reported back on this second pre-trial. Mr. Gordon is adamant that he agreed to plead guilty because his trial counsel told him that the plea judge had said that he would impose no more than an additional six months in custody.

[14] At that meeting with his counsel following the second pre-trial, Mr. Gordon signed a document titled “INSTRUCTIONS TO COUNSEL FOR A GUILTY PLEA”, which included the following acknowledgment:

I understand the Crown Attorney will be seeking an 8 to 10 year custodial sentence.

I understand that this will be a contested sentencing and the Defence will be asking for a sentence of time served.

I understand that the Judge will not be bound by either my counsel or the Crown’s position and the Judge has discretion to impose a more severe penalty if they find it appropriate to do so.

[15] Mr. Gordon then pleaded guilty. Before accepting the guilty plea, the plea judge conducted a plea inquiry, during which Mr. Gordon indicated that he understood that the plea judge could impose a sentence higher than any joint submission made by his lawyer and the Crown:

[The plea judge:] There may be a joint submission before the Court, right? A joint submission means that the Crown and the Defence have agreed on what the penalty is; there might be one. But just so you know, I’m not bound by that. Okay? Like I can give a higher sentence or a lower sentence if I think it is appropriate. So are you aware of that?

[Mr. Gordon:] Yes

[17] The plea judge pronounced his sentence on February 10, 2023. He imposed a global sentence of seven years. Deducting Summers credit at a rate of 1.5 days for each day in pre-trial custody, this left a sentence of two-and-a-half years to serve.

[18] Mr. Gordon’s evidence is that he was “shocked” by the sentence because the time remaining to serve was five times higher than what he believed the plea judge had “promised”. After the plea judge read out his reasons, Mr. Gordon stood up and asked if he could speak. His trial counsel then asked to meet with Mr. Gordon privately. In that meeting, trial counsel told Mr. Gordon that nothing could be done about the sentence at that time and that he would have to raise the issue on appeal.

C. PRINCIPLES APPLICABLE TO SETTING ASIDE A GUILTY PLEA

[19] The Supreme Court has emphasized that the plea resolution process is central to the criminal justice system, and that maintaining the finality of guilty pleas is “important to ensuring the stability, integrity, and efficiency of the administration of justice”: R. v. Wong, 2018 SCC 25, [2018] 1 S.C.R. 696, at para. 3. At the same time, “the finality of a guilty plea also requires that such a plea be voluntary, unequivocal and informed”: Wong, at para. 3 (emphasis added).

[20] In order to strike a guilty plea on the basis that it was uninformed, the court must be satisfied that (1) the appellant was misinformed about or unaware of information that he needed to have in order to give an informed plea (the “information” component), and (2) he suffered prejudice amounting to a miscarriage of justice (the “prejudice” component): R. v. Espinoza-Ortega, 2019 ONCA 545, 146 O.R. (3d) 529, at para. 35.

D. ANALYSIS

[22] Mr. Gordon submits that he meets both branches of the inquiry for setting aside a guilty plea on the basis that it was uninformed: 1) his plea was uninformed because he understood that he would only serve six months beyond pre-trial custody; and 2) he suffered prejudice because he would not have pleaded guilty if he had known that he faced the possibility of serving any time beyond an additional six months. Based on the record before the court, I am satisfied that Mr. Gordon has established both criteria.

(1) The guilty plea was uninformed

[23] For a guilty plea to be informed, the accused must be aware of the allegations made by the Crown and the effect and consequences of the plea: R. v. Girn, 2019 ONCA 202, 145 O.R. (3d) 420, at para. 51; R. v. T. (R.) (1992), 10 O.R. (3d) 514 (C.A.), at p. 519. If the accused establishes that he was unaware of the consequences of the plea, the court will consider the gravity of those consequences objectively: as held in Wong, at para. 34, “this step objectively assesses the seriousness of the unknown legal consequence” (emphasis added).

[24] I accept that the plea was uninformed in this case because Mr. Gordon did not understand that he could be sentenced to more than an additional six months in custody. I further accept that, viewed objectively, this was a serious unknown consequence.

[25] I recognize that the appellant provided signed instructions to his lawyer in which he affirmed that he understood: (1) that by pleading guilty, he acknowledged that he had committed the offences; (2) that the Crown would be seeking an 8- to 10-year custodial sentence; (3) that the plea judge was not bound by the positions of Mr. Gordon’s trial counsel or Crown counsel; and (4) that he could not withdraw his guilty plea if he disliked the sentence imposed. I also recognize that the plea judge conducted a full guilty plea inquiry.

[26] However, I am satisfied that the appellant pleaded guilty because he believed the plea judge had provided an assurance at the second judicial pre-trial that he would not impose a sentence exceeding six additional months in custody. Whether the plea judge provided such an assurance is very much in dispute. But I do not have to resolve that issue. What matters is whether Mr. Gordon has demonstrated that this is the information he received from his trial counsel and that he believed it…

[27] This evidence may be hard to believe on its own, especially given that it contradicts Mr. Gordon’s signed instructions. However, it was confirmed by Mr. Gordon’s trial counsel, who swore an affidavit stating that the plea judge provided this assurance and that he shared this information with Mr. Gordon…

…Moreover, when cross-examined on his affidavit, Mr. Gordon’s trial counsel again confirmed that he assured Mr. Gordon “[t]his was going to happen”:

A. This was going to happen. That Justice Goldstein was going to do this, is what Mr. Gordon understood, and that’s what I communicated to him … [Emphasis added.]

[28] The Crown argues that the length of a sentence is not the type of serious unknown consequence that warrants setting aside a guilty plea…

here, Mr. Gordon understood that he would only spend another six months in custody, whereas the sentence imposed was another two-and-a-half years or five times longer than he expected. Objectively, this rises to the level of a serious unknown legal consequence.

[31] This case is exceptional. It would be rare for counsel to provide an assurance to their client that a plea deal will lead to a specific sentence, especially in circumstances where there is no joint submission. It would also be rare for counsel to give evidence that they provided a verbal assurance regarding a specific sentence despite requesting that their client sign a document acknowledging that the plea judge may impose a different sentence. However, in this case, given the unequivocal evidence from both Mr. Gordon and his trial counsel, I accept that he understood that the plea judge had provided an assurance that, if he pleaded guilty, his sentence would be no more than an additional six months in custody. I further accept that he therefore misunderstood an objectively serious consequence of his guilty plea. The information component is therefore made out.

(2) Mr. Gordon suffered prejudice

[32] Prejudice is to be assessed subjectively: Wong, at para. 6; Espinoza-Ortega, at para. 35. To demonstrate prejudice, the appellant must file an affidavit to establish that he would either have (1) pleaded differently, or (2) pleaded guilty but with different conditions: Wong, at para. 19; Espinoza-Ortega, at para. 36.

[33] In his affidavit and during cross-examination, Mr. Gordon stated unequivocally that he would not have pleaded guilty if he understood that he could spend more than an additional six months in custody. His conduct prior to the guilty plea is entirely consistent with this position…

…Mr. Gordon refused to plead guilty, on the basis that he did not want to serve longer than an additional three more months in custody.

[34]…as the Supreme Court instructed in Wong, at paras. 12 and 25, prejudice is assessed on a subjective basis and not on the basis of what a reasonable person in the accused’s position would know or decide. In this case, Mr. Gordon’s evidence, including the evidence of his behaviour prior to the guilty plea, show clearly that he would not have pleaded guilty if he had understood that there was a risk of more than a further six months in custody.

E. DISPOSITION

[36] I would allow the appeal, set aside Mr. Gordon’s guilty plea and order a trial.

R v JC, 2025 ONCA 230

[March 24, 2025] Amicus Curiae: the Need for an Amicus Approximating Defence Counsel [Reasons by Coroza J.A. with A. Harrison Young and S. Gomery JJ.A. concurring]

AUTHOR’S NOTE: This case examines the evolving role of amicus curiae in criminal proceedings, particularly between Ontario v Criminal Lawyers’ Association of Ontario (2013) and R v Kahsai (2023). The accused, in a dangerous offender hearing, actively assisted the Crown in seeking an indeterminate sentence, effectively abandoning his own defence. The trial judge failed to expand the role of amicus to counterbalance this, leading to an unfair proceeding.

The Court of Appeal overturned the decision, emphasizing that in cases where the accused does not mount any defence, the judge must ensure an adversarial perspective to maintain fairness. This case reinforces the judicial duty to safeguard due process in dangerous offender hearings.

I. OVERVIEW

[2] The appellant represented himself during the dangerous offender hearing. The appellant’s position was an unusual one – he wanted the court to declare him a dangerous offender and impose an indeterminate sentence – a position which appears to have stemmed from his frustration with delays in the process. Throughout the proceedings the appellant was disruptive, displayed a defeatist attitude, changed his mind several times, and constantly expressed frustration with the length of the process. The experienced sentencing judge faced the extraordinary challenge of maintaining a fair proceeding.

[3] The sentencing judge appointed amicus to assist him with that task. However, based on the sentencing judge’s understanding of the existing jurisprudence from the Supreme Court of Canada, the sentencing judge limited the scope of the amicus appointment.

[4] The appellant appeals. The crux of his argument is that a miscarriage of justice arose in the proceedings. The appellant contends that the limited appointment of an amicus without an adversarial role doomed the procedural fairness (and the appearance of fairness) of the hearing. The appellant also argues that the sentencing judge conflated the two stages of a dangerous offender analysis pursuant to the Supreme Court’s decision in R. v. Boutilier, 2017 SCC 64, [2017] 2 S.C.R. 936. He seeks a new hearing.

[5] …to the extent that the sentencing judge restricted the mandate of amicus based on an understanding that the jurisprudence prevented him from assuming any adversarial functions, that is an error in principle: R. v. Kahsai, 2023 SCC 20, 483 D.L.R. (4th) 199, at para. 72.

[6] That is what happened in this case. In the end, I am satisfied that the sentencing judge would have appointed an amicus with a broader adversarial role for the appellant if he had the benefit of the Supreme Court of Canada’s decision in Kahsai. In my respectful view, a different amicus appointment would have impacted the fairness or perceived fairness of the appellant’s hearing. The appellant has discharged his burden of proving that the appearance of unfairness was serious enough to taint the administration of justice and I would allow the appeal.

(b) The Appointment of Amicus

[12] Given the seriousness of the matter, the sentencing judge and Crown agreed that an amicus appointment should be made. The appellant indicated that he did not want an amicus to represent him, but he did not object to the appointment. The appellant also indicated that he did not intend to raise any defence and would, in fact, be seeking to elicit evidence to support the Crown’s case.

[16] Part way through the proceedings, the appellant apologized for his behavior and indicated that he wanted to be represented by counsel. The sentencing judge agreed to adjourn the hearing and indicated that he was willing to make a Rowbotham order should legal aid be denied. The appellant consented to working with trial amicus to find representation.

[17] Unfortunately, after expressing his frustration with the proceedings, the appellant returned to his previous position, stating “I do not want to have the weight on my shoulder anymore of a chance of getting out ever.” Again, he asked to be declared a dangerous offender and to receive an indeterminate sentence.

[18] When offered the opportunity to cross examine the Crown’s witness from Correctional Services, the appellant asked only questions about the location where dangerous offenders are incarcerated, the timeframe for assessment, and how he could ensure that he is placed in segregation.

[19] Throughout most of the hearing, the appellant adopted the position of the Crown. When asked whether he wished to call evidence, the appellant refused to call his family and chose to testify himself. He went out of his way to provide examples of his violent behavior and to point out that he wanted to be declared a dangerous offender and receive an indeterminate sentence.

(d) Decision Below

[20] At the outset of his reasons for judgment, the sentencing judge raised concerns over the fairness of the proceedings, stating:

As a result, the defendant has been unrepresented at this hearing by his own choosing. I cannot force counsel on him. Crown counsel has been exceptionally fair but necessarily is adverse in interest to the defendant. The limited role now permitted for amicus pursuant to recent Supreme Court jurisprudence aggravates the situation. Amicus has very ably and diligently performed his duty, but the problem is that appointing amicus is something of a sham. It is the defendant, not the Court, who requires counsel.

Accordingly, I find myself in the position of presiding over an application with the gravest potential consequences to the defendant while being uneasy about the fundamental fairness of the proceeding. Without counsel, the defendant has been severely disadvantaged in his ability to present his case and challenge the Crown’s, though he has shown little interest in doing either. More significantly, given the position he has taken in his “defence”, he has gone without badly needed advice and has been left unrestrained and guided by his emotions and questionable judgment to present a suicidal defence. [Emphasis added.]

[21] After considering the relevant law, the sentencing judge found that the appellant is a dangerous offender and sentenced him to an indeterminate sentence…

IV. ANALYSIS

ISSUE 1: Was there a miscarriage of justice arising from the absence of an effective amicus?

(a) The Test for Miscarriage of Justice

[27] To succeed in this appeal, the appellant must persuade this court that the amicus appointment in his hearing created an irregularity so severe that it rendered his hearing unfair in fact or in appearance. He must persuade us that the gravity of the irregularity created such an appearance of unfairness that it would shake the public confidence in the administration of justice: see Kahsai, at paras. 29, 67; and s. 686(1)(a)(iii) of the Criminal Code.

(c) Ontario v. Criminal Lawyers’ Association of Ontario

[29] When the appellant refused to retain counsel and chose to represent himself, the Crown agreed with the sentencing judge’s decision to appoint amicus. At the time of the hearing, the sentencing judge noted that there was a limited role permitted for amicus pursuant to the Supreme Court’s decision in Ontario v. Criminal Lawyers’ Association of Ontario, 2013 SCC 43, [2013] 3 S.C.R. 3 (“CLA”). In CLA, the Supreme Court held that amici cannot take on the role of defence counsel: at para. 56. In this regard, the court raised several concerns, including the potential conflict between an accused’s constitutional right to represent themselves and an amicus appointed with the role of defence counsel. The court concluded that an amicus clothed with the duties and responsibilities of defence counsel could no longer be called a “friend of the court”.

[30] Given the sentencing judge’s comment in his reasons that “appointing amicus is something of a sham”, he undoubtedly believed that appointing an amicus with a more robust and adversarial role was restrained by CLA. This is not surprising. As summarized by Code J. in R. v. Jaser, 2014 ONSC 2277, at para. 34, the view of many trial judges was that the CLA judgment “limited the trial judge’s duty to assist the self-represented accused by making it clear that amicus can do no more than what the trial judge can do.”

(d) R. v. Kahsai

[31] After the appellant’s dangerous offender hearing concluded, the Supreme Court released its decision in Kahsai. The court in Kahsai went on to clarify its position in CLA, stating that, in exceptional circumstances, where required for trial fairness, amici may take on adversarial roles, including cross-examination and closing argument, as long as an amicus does not actually step into the shoes of defence counsel. The court also reiterated that the concerns raised in CLA remain relevant and are to be considered by judges when appointing amici.

[32] Exceptional cases that may warrant the appointment of an amicus include situations when an unrepresented accused is found fit to stand trial but suffers from mental health challenges; when an unrepresented accused refuses to participate; or when an adversarial perspective is required for a fair adjudication of the case: Kahsai, at para. 57. [Emphasis by PJM]

[33] In sum, the role of an amicus must balance an accused’s right to conduct their own defence with what is necessary for trial fairness. The court summed up the applicable principles at para. 64:

In sum, in the vast majority of cases, the responsibilities of the trial judge and the Crown will suffice to ensure trial

fairness. Once it is determined that amicus is required, the trial judge retains wide discretion to appoint amicus with functions that are responsive to the needs of a case. This may include adversarial functions where necessary for trial fairness — for example, to restore balance to a proceeding when an accused chooses to self-represent and puts forward no meaningful defence. In tailoring the scope of the role for the amicus, the judge will consider the nature of the role of amicus as friend of the court and the circumstances of a case, including how the accused exercises their constitutional rights and what is needed to ensure a fair trial. While there are necessary limits to the adversarial functions that amicus can perform, the scope is broad enough to accommodate what is necessary for trial fairness in a particular case. [Emphasis added.]

[34] The court also held that where a trial judge has failed to give amicus a broader adversarial mandate based on a misunderstanding of CLA, this is an error in principle.

(e) The Limited Appointment of Amicus in this case

[35] As I mentioned above, the sentencing judge in this case did not have the benefit of Kahsai at the time of the hearing. I am satisfied that if the sentencing judge had seen the more recent guidance of the Supreme Court of Canada, he would not have considered the role of the amicus to be restricted and would have assigned amicus a more robust adversarial role.

(f) Amicus with a more robust role was required

[40] I disagree that a more robust amicus mandate in this case would have created an “adversary” that could undermine the appellant’s right to direct his own defence in a manner that is inconsistent with CLA or Kahsai. An amicus, even when given adversarial functions, remains a “friend of the court”. And while “[g]enerally, the court must respect the strategic choices of an accused person who is fit to stand trial, even where those choices seem irrational or unwise”, this does not relieve a sentencing judge of their responsibility to ensure that procedural fairness is “jealously guarded and strictly enforced” in dangerous offender proceedings: Kahsai, at para. 58; R. v. Walker, 2019 ONCA 765, 381 C.C.C. (3d) 259, at para. 25.

[41] In my view, this is precisely the type of case in which a more robust and perhaps adversarial perspective from amicus was necessary for the case to be justly adjudicated: Kahsai, at para. 57. I wish to emphasize the appellant’s position was unusual. He was not trying to defend himself. To the contrary, the appellant was trying to join the Crown in its efforts to have him declared a dangerous offender and he was requesting a specific sentence. But there exists no right/entitlement of an offender to receive an indeterminate sentence of incarceration. Amicus assisting the judge to be fully equipped with a broad perspective would not have meant being an adversary against the appellant in this context

[43] In the circumstances of this case, the sentencing judge’s duty was to engage in a full assessment of the evidence and determine whether he was satisfied that the evidence in front of him established that the statutory criteria in s. 753 were met, as informed by relevant jurisprudence. The sentencing judge explicitly recognized this when he commented, “[t]he defendant’s position of course does not relieve me of the duty to make my own determinations.” However, the Crown’s evidence went largely unchallenged in a proceeding that has profound legal consequences for the appellant. To restore balance, the sentencing judge required amicus to “test the strength of the Crown’s case to put the Crown to its burden” of satisfying the criteria under s. 753. In my view, doing so would have better protected the appellant’s interests. It was important that the sentencing judge, in this case, have a perspective adversarial to the Crown to test the Crown’s arguments supporting a dangerous offender finding and indeterminate sentence.

(g) What are more robust functions that amicus could have been assigned?

[44] The restricted role given to amicus left the sentencing judge with only one perspective on the evidence being presented to him, and as he noted in his reasons, “Crown counsel has been exceptionally fair but necessarily is adverse in interest to the defendant.” If the sentencing judge had the benefit of Kahsai, I am satisfied that he would have permitted a wider scope for the amicus in this case to ensure fairness in the proceedings.3 [PJM Emphasis]

[45] I will provide some examples of the issues that may have been explored by amicus had a limited appointment not been made.

[46] First, amicus could have been specifically appointed to conduct a more thorough cross-examination to explore and test the s. 752.1 assessment psychiatrist’s opinion evidence. The following are general points (not specific to Dr. Woodside) as to what could have been explored in cross-examining a psychiatrist who did a s. 752.1 assessment, to test the opinion evidence and flesh out what its potential limitations may be. The amicus could have specifically highlighted the following areas that could potentially be explored:

 Whether there were conditions or exceptions limiting the scope of the opinion that the assessor had not yet expressed;

 Clarification of what the limits of the risk assessment tools are, and what they do or do not indicate;

 Whether there were significant gaps in the assessor’s grasp of the information on which the opinion was based;

 Whether reliable details favourable to the accused in the body of information on which the assessor based his opinion were not factored into the opinion, and if they were missed;

 Whether they would have had an effect on the opinion;

 Whether there were any significant points of inconsistency between what the assessor wrote in the report and what the assessor stated in the in-court testimony; and

 Whether the assessor’s testimony strayed outside his area of expertise or into speculation. [Emphasis by PJM]

[47] Second, amicus could have been appointed to make closing submissions on Boutilier, and could have drawn the sentencing judge’s attention to the way in which Boutilier explains the distinction between whether, first, an offender should be designated a dangerous offender and, if so, whether an indeterminate sentence should be imposed. As pointed out by counsel for the appellant, during the Crown’s submissions at the hearing, the sentencing judge commented, “I can’t imagine being satisfied a person meets the criteria for the designation yet [f]ind that they don’t meet the criteria for the indeterminate sentence.” Counsel for the appellant argues that the sentencing judge erred in his analysis because he appears to have conflated the designation and sentencing stage of the s. 753 analysis.

[48]…Nevertheless, it could have been helpful for amicus to draw the sentencing judge’s attention to Boutilier, which explains how treatment prospects that are not “compelling” enough to affect a sentencing judge’s finding of dangerousness may still affect the sentencing decision…

[49] Third, I agree with the appellant that amicus could have responded to some of the Crown’s arguments regarding designation and penalty…

[50] Fourth, amicus could have discussed with and explained to the appellant the consequences of certain decisions, including the potential implications of deciding to obtain, or not obtain, a second opinion from another psychiatrist…

[51] I recognize that, in the end, the appellant dug his heels in and did not appear to want a second report. However, at other points in the proceeding, the appellant indicated his desire for a second assessment. Some of these occurred after the amicus appointment. I appreciate that it is difficult to predict what might have happened in these circumstances, but it is certainly possible that amicus could have provided practical assistance to the appellant in exploring funding to obtain a second psychiatrist (just as the trial judge assigned to amicus the role of assisting the appellant to retain counsel).

(h) Did a Miscarriage of Justice Occur?

[52] It is difficult to say with any certainty that the assistance of amicus would have led to a different outcome. However, the issue raised by the appellant is concerned with the integrity of the administration of justice. “A miscarriage of justice may be found where anything happens in the course of a trial, including the appearance of unfairness, which is so serious that it shakes public confidence in the administration of justice” (emphasis added): R. v. Davey, 2012 SCC 75, [2012] 3 S.C.R. 828, at para. 51; Kahsai, at para. 67. The analysis of whether a miscarriage of justice occurred is “conducted from the perspective of a reasonable and objective person, having regard for the circumstances of the trial”: Kahsai, at para. 67.

[55] What occurred here was not a minor irregularity. A dangerous offender proceeding is one of the most serious proceedings known to law. As Fairburn J.A. (as she was then) put it in Walker, at para. 24: “[i]t not only asks whether a person should have a label of dangerousness attached to him or her for life, but also whether the person should be at risk of having his or her right to liberty removed for life.”

[56] While Walker involved a case where the amicus actively advocated for something detrimental to a self-represented person, the amicus in this case was restricted based on a misunderstanding of the law. Initially, amicus was told that he was not permitted to ask questions. Eventually, he was permitted to ask questions but only asked a few during cross-examination and did not make any submissions at all during closing submissions. The administration of justice would have been better served had amicus been given a more robust mandate to balance out the proceedings. The sentencing judge’s statements make clear that he would have done so if he believed he could.

[57] I am satisfied that the appellant has discharged his burden of demonstrating that an objective person looking at the hearing that resulted would see it as so unfair that it would shake their confidence in the justice system. One need look no further than the sentencing judge’s own expressed discomfort with the fairness of the proceeding in his reasons. The sentencing judge found the appellant to be “severely disadvantaged in his ability to present his case and challenge the Crown’s”.

[59] Reluctantly, I conclude that a miscarriage of justice occurred, and I would allow the appeal.

VI. DISPOSITION

[62] For these reasons, the dangerous offender finding, and indeterminate sentence are set aside, and a new hearing is ordered.

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Written By Pawel Milczarek

Pawel is a partner at Sitar & Milczarek. When he’s not litigating he writes the Defence Toolkit blog.

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