ONTARIO SUPERIOR COURT OF JUSTICE
B E T W E E N:
HIS MAJESTY THE KING
Ryan Mullins, for the Crown
- and -
JAMAR BAILEY
Self-represented
HEARD: August 11, October 1, November 12, 2025; January 12, April 7, May 19, June 25, 2026
SENTENCING REASONS
D.E. HARRIS J.
1This is a judgment to explain the reasons for the sentence I will impose on Jamar Bailey for the offences of robbery with a firearm, pointing a firearm and being in a vehicle knowing that it contained a firearm. Mr. Bailey asked for the mandatory minimum of five years for robbery with a firearm; the Crown asks for between 7 and 8 years. It is agreed that the pointing a firearm count be stayed pursuant to Kienapple.
2A full account of the evidence and factual findings can be found in the reasons finding Mr. Bailey guilty: R. v. Bailey, 2025 ONSC 3401. In summary, the victims, William Escoffery and his brother Lamor, advertised Play Stations and an Xbox on Snapchat. A person using the name “cookiestoronto” replied and a deal was struck for $4320. At the appointed time in the early evening hours, a black Mazda with two men in it arrived at the Escoffery residence. Travis Escoffery had just arrived home from work. The merchandize was loaded into the car. A skirmish broke out and one of the two buyers from the Mazda pulled out a handgun, threating the victims with it. The men then got in their car and drove away. As they did, the passenger stuck his arm out the window of the car and fired a gunshot straight up into the air. A 9mm shell casing was later found nearby by the police. This proved that the gun was real and not an imitation.
3The Crown proved at trial that Mr. Bailey was one of the two men who committed the robbery. The “cookiestoronto” handle was his. The Mazda was his common law wife’s. The case was proved beyond a reasonable doubt although it was not proved whether Mr. Bailey was the person who wielded the handgun or fired it in the air. If he was not the principal, he was a party with full knowledge of the circumstances and plan.
THE OFFENCE
4Looking first at the seriousness of the offence, robbery with a firearm under s. 344(1)(a)(i) of the Criminal Code, R.S.C. 1985, c. C-46 no matter the circumstances, is a very serious offence. As was said in R. v. Hilbach, 2023 SCC 3, the case that upheld the five year mandatory minimum, at para. 6: “The risk of violence and psychological trauma from any robbery involving a firearm is acute.” (Emphasis in original). The court when describing the offence later in the judgment, said this,
53…As this Court wrote in R. v. Felawka, 1993 CanLII 36 (SCC), [1993] 4 S.C.R. 199, when a firearm is used to threaten or intimidate, it “presents the ultimate threat of death to those in its presence” (p. 211). Prohibited firearms are among the most potent tools in the commission of crime…
54 The harmful consequences of using a restricted or prohibited firearm in a robbery are readily identified. There is the risk of death or life-altering physical injury for victims and bystanders if the weapon is discharged. Even if the weapon is not fired, exposure to this threat carries the risk of profound psychological harm
5See also see R. v. Chizanga, 2024 ONCA 545, 172 O.R. (3d) 241, at paras. 131-37, aff'd on other grounds 2025 SCC 9, 446 C.C.C. (3d) 141; R. v. Danvers, (2005) 2005 CanLII 30044 (ON CA), 199 C.C.C. (3d) 490 (Ont. C.A.), at para. 77; R. v. Brown, 2010 ONCA 745, 277 O.A.C. 233, at para. 14; R. v. Ferrigon, 2007 CanLII 16828 (Ont. S.C.), at para. 25; R. v. Kawal, 2018 ONSC 7531 at para. 16, aff’d on other grounds, 2025 ONCA 462.
6The introduction of a handgun and the threat of instant death into a small private transaction on a placid residential street involving several different people has its own dangers. In the skirmish that took place, the gun could have gone off accidentally. Someone could easily have been maimed or killed. As described in Hilbach, the psychological trauma to the victims by which I include the four people on the scene who were involved in selling the items, must have been profound. The two Escofferys, Lamor and Travis, who filed victim impact statements described the shock and fear. It stayed with them five years afterwards, as one would expect.
7Travis’ piece of mind in the residential area of the family home has vanished. He has become more vigilant about his surroundings, and his sense of safety has been badly disturbed. Lamor says that his online business buying and selling has been reduced and that his relationship with his brother William whom he carried on the business with has not been the same. These are foreseeable ramifications from the nature of an offence of this kind.
8The primary sentencing objectives with all crimes of this seriousness are denunciation and deterrence. The firearm is the key circumstance justifying the mandatory minimum. In addition, deterrence is important to protect the private selling and buying marketplace, a major economic activity these days. When buyers meet sellers both parties ought to feel comfortable and secure. Violence of the kind here, exploiting the vulnerability of small commercial vendors, unsettles and puts a damper on private transactions.
THE OFFENDER
9Rehabilitation is important on this sentencing. Mr. Bailey’s presentence report was positive. He is 37 years old and has two children. He has a fail to comply with probation order conviction from 2012 and a trafficking in drugs conviction in Toronto from 2015 for which he received a substantial fine and probation.
10Mr. Bailey was raised in Malton by his mother and grew up with his two younger maternal half-sisters. His father resides in Jamaica and when he was young he visited him every year. The family was tight knit growing up and were regular church goers.
11The family moved to Rexdale in Toronto when Mr. Bailey was in the third or fourth grade. It was a bad area and he heard gunshots on numerous occasions. His family was, in his words, “lower class”. Mr. Bailey talked about being racially profiled by the police and was stopped because he “fit the description” of a suspect. Mr. Bailey said he became desensitized to the mistreatment by the police and got used to it as a Black man. Mr. Bailey commented that he only experienced racism in the legal world, not elsewhere.
12Mr. Bailey’s half sister Ms. Latoya Rainford said that because Mr. Bailey was the only male in the home, the family would rely on him for many things, such as rides to school. His other sister, Aaiyah Adamson said that Mr. Bailey had good relationships with other family members and because he began working at a young age, would often provide for her and her sister.
13The family moved to Brampton in 2012-2013. Mr. Bailey currently resides with his uncle and cousin in Mississauga. His two children are a nine-year-old daughter and three year old son, with Chakeba Kelly. She testified at trial under subpoena for the Crown. The daughter has a slight delay and the son is autistic and non-verbal. Mr. Bailey described himself as a “pro-active” father and credits his children with changing his life for the better. All the people contacted for the pre-sentence report spoke highly of Mr. Bailey’s involvement with his children and noted that this is a source of pride for him.
14Mr. Bailey graduated high school with good marks and then completed one year of a two-year post-secondary program in social work. He dropped out to work. Mr. Bailey told the pre-sentence report author that he is open to taking a trades program in the future.
15Mr. Bailey started working in grade nine and has worked steadily ever since. He has been working for his aunt’s trucking company since approximately 2012. His aunt, Megan Bailey, who testified in court for the defence, described him as a good worker and a good father figure. She said that many of her customers have sent her emails praising Mr. Bailey. There has never been an issue with him. She added that he loves his family.
16The pre-sentence author wrote that Mr. Bailey presented as polite, respectful and engaged throughout the interview process. Having presided for many days over Mr. Bailey’s trial in which he was self-represented, that was certainly my impression too. Mr. Bailey was unfailingly respectful and courteous. This might have been partially to put on a good face in front of the person who held his fate in his hands but I don’t think so. I had a good impression of his character. The gun fired in this case and the prior drug dealing conviction could be indicative of being part of the drug underworld so prevalent in our jurisdiction. There were pictures of handguns on his phone which I ruled inadmissible at trial. While he seems to have had some minor involvement in that underworld, he is a hard-working family man. I view this offence as an aberration for him.
17I also had a good impression from her testimony of the mother of his children, Ms. Chakeba Kelly. She was put in a difficult spot in this trial testifying for the Crown. She testified in-chief that as she had told the police in a statement at the time the search warrant was executed, the PlayStation found in the home where she lived with Mr. Bailey was brought into the home sometime in January, 2022, soon after the robbery. She could not practically speaking deviate from this statement in her trial testimony. There was a video found on Mr. Bailey’s phone of their young daughter playing with great joy and enthusiasm on the machine. Sadly, it seems Mr. Bailey decided to please his daughter by acquiring the PlayStation through criminal means. That was short sighted in the extreme and a very poor decision, needless to say. Now he will be away from his family for an extended period, a significant mitigating factor I have taken into account on this sentencing: R. v. Habib, 2024 ONCA 830.
18Looking at his antecedents, his strong dedication to family and his children, and his good work history and ethic, I do not expect Mr. Bailey to commit other serious criminal offences. His prospects for rehabilitation are good. The need for specific deterrence is not pressing. It is not zero, however. He has two other entries on his criminal record and this offence is serious, involving a firearm.
19It is important to reflect on the experience of Mr. Bailey while a young person or man being stopped by the police in a “low-income” neighbourhood in his youth because he “fit the description” of a suspect. He was racially profiled. He told the pre-sentence report author that eventually he became desensitized to mistreatment at the hands of the police. This, regrettably, is a relatively common phenomenon. It was said by the Supreme Court in R. v. Le 2019 SCC 34:
95 The impact of the over-policing of racial minorities and the carding of individuals within those communities without any reasonable suspicion of criminal activity is more than an inconvenience. Carding takes a toll on a person's physical and mental health. It impacts their ability to pursue employment and education opportunities (Tulloch Report, at p. 42). Such a practice contributes to the continuing social exclusion of racial minorities, encourages a loss of trust in the fairness of our criminal justice system, and perpetuates criminalization (see N. Nichols, "The Social Organization of Access to Justice for Youth in 'Unsafe' Urban Neighbourhoods" (2018), 27 Soc. & Legal Stud. 79, at p. 86; see also Ontario Human Rights Commission, Under Suspicion: Research and Consultation Report on Racial Profiling in Ontario (2017), at pp. 31-40).
20It is not possible to know the exact circumstances of the police conduct in Mr. Bailey’s case. That is intrinsic to the problem. There cannot obviously be mini-trials to examine fleeting events from many years ago. But Mr. Bailey’s credibility and reliability is partially reinforced by the comment that it is only in the legal system that he has suffered racism. He is not accusing the entire community or other sectors of racial unfairness towards him.
21I believe him. His remarks are reasonable, measured and are not tainted by hyperbole. And many others have had the same experience. The fact is the presence of the police in Rexdale was inimical to Mr. Bailey. Police are looked up to and wield considerable authority, particularly in low-income communities. They are both respected and feared. The police are representatives and ambassadors of the community. To be mistaken on more than one occasion by persons in authority for what must have been another Black man and accused of committing criminal offences is bound to have an effect on a person. He was indiscriminately grouped with wrong doers for the sole reason that he had the same skin colour. That must have been humiliating and profoundly dispiriting. It could well have conveyed to Mr. Bailey, consciously or unconsciously, that he was not a full-fledged member of mainstream society, that he was not fully accepted. This impression was bred in the bone.
22In R. v. Morris, 2021 ONCA 680, the Court of Appeal said,
79 The social context evidence can, however, provide a basis upon which a trial judge concludes that the fundamental purpose of sentencing, as outlined in s. 718, is better served by a sentence which, while recognizing the seriousness of the offence, gives less weight to the specific deterrence of the offender and greater weight to the rehabilitation of the offender through a sentence that addresses the societal disadvantages caused to the offender by factors such as systemic racism.
86 …we accept wholeheartedly that sentencing judges must acknowledge societal complicity in systemic racism and be alert to the possibility that the sentencing process itself may foster that complicity. A frank acknowledgement of the existence of, and harm caused by, systemic anti-Black racism, combined with a careful consideration of the kind of evidence adduced in this case, will go some distance toward disassociating the sentencing process from society’s complicity in anti-Black racism.
23I cannot say, nor is it necessary to say on this record in view of the mandatory minimum, that these racial profiling experiences of Mr. Bailey’s contributed to his criminal conduct. But the racial denigration Mr. Bailey suffered certainly has implications for specific deterrence and rehabilitation. The Court further added in Morris,
102 Social context evidence can also be relevant on sentencing even if it does not tend to mitigate the offender’s moral culpability. As indicated earlier, social context evidence can provide valuable insight, both with respect to the need to deter the offender from future conduct, and the rehabilitative prospects of the offender. Evidence about an offender’s background and circumstances allows the sentencing judge to more accurately assess how sometimes competing objectives of sentencing, such as rehabilitation and denunciation, can best be blended to produce a sentence that accords with the proportionality principle and serves the fundamental purpose of sentencing articulated in s. 718.
103 For example, evidence that an offender has had frequent and confrontational contact with the police may mean one thing in one community, but quite another in a community in which the influences of anti-Black racism have shaped a confrontational and adversarial relationship between the police and members of the community, especially young Black men. [Emphasis added]
24The police as highly regarded leaders in the community were teaching exactly the wrong lesson when they falsely accused Mr. Bailey based on him being Black. A false accusation of criminality carries stigma. It hurts. And a racially based accusation segregates a person and brands him by his skin colour, ignoring all other facets of his identity, autonomy and ultimately, his individual personhood. This is indicative of broader social and economic flaws which perpetuate unfairness and injustice in our society.
SENTENCE TO BE IMPOSED
25It is of some importance that the Supreme Court in Hilbach held at paragraph 80 that in the circumstances of that case, a robbery of a convenience store with an unloaded sawed off shotgun in which the accomplice assaulted two employees, the mandatory minimum of five years, although not grossly disproportionate or meeting the lower standard of demonstrably unfit, “departed from principles of parity and proportionality.” Granted, Hibach was 19 years old and came from a hearbreaking background of prejudice against indigenous people. But it is clear that were it not for the mandatory minimum, the Court would have held that a lower sentence was appropriate.
26I think there are similarities of a general kind in this case. The gun was loaded which makes the offence more serious but may not greatly alter the sentence to be imposed. Carrying the gun in a motor vehicle is an aggravating circumstance but not of enormous weight. The musings of the Supreme Court in Hilbach suggest that the sentence here, although the circumstances of the offence and the offender are quite different, need not be in the range reommended by the Crown.
27There are also specific mitigating factors. The offence was four and a half years ago and there have been no problems while out on bail. The time that has gone by is itself a mitigating factor: R. v. Hartling, 2020 ONCA 243 at paras. 115-122. And Mr. Bailey has been on virtual house arrest since the beginning and is due significant mitigation for this: R. v. Downes, (2006), 2006 CanLII 3957 (ON CA), 79 O.R. (3d) 321 (C.A.); R. v. Joseph, 2020 ONCA 733, 153 O.R. (3d) 145, at para. 108. While that cannot bring a sentence below the minimum, it is imporant in evaluating the range of sentence recommended by the Crown.
28In the end, the public interest does not require a sentence above the minimum. The principles of general deterrence and denunciation are sufficiently vindicated by a five year sentence. Practically speaking, two or three years more as advocated by the Crown will add little or nothing to these principles. A person contemplating such an offence will not be any more deterred by a seven or eight year sentence than they would be by a five year sentence. The added denunciation is not significant either. Meanwhile, the negative impact on Mr. Bailey from additional jail time would be substantial. Because of its detrimental effects, when additional jail is unncessary to satisfy the principles of sentencing, it ought not to be ordered. That is the principle of restraint codified in s. 718.2(e) of the Criminal Code. It applies here.
29Therefore, the sentence will be five years minus the six days for credited pre-trial actual custody of four days. The apprortionment will be five years minus six days on the robbery count and a suspended sentence on the knowledge of the firearm in the car count.
30Ancillary orders: s. 109(2) for 15 years and life; DNA databank order; Forfeiture of the Playstation seized and cables, controller under s. 462.37 of the Code; Restitution of $3440 within three years for consoles not recovered ($2640 to William; $800 to Lamor); Non communication orders under s. 743.2(1) with resepect to William, Lamor and Travis Escoffery and Alexie-Ann Douse.
D.E. HARRIS J.
DATE: June 26, 2026
CITATION.: R v. Bailey, 2026 ONSC 3745
COURT FILE NO: CR-24-26
DATE: 2026 06 25
ONTARIO SUPERIOR COURT OF JUSTICE
B E T W E E N:
HIS MAJESTY THE KING
- and -
JAMAR BAILEY
REASONS FOR JUDGMENT
D.E. HARRIS J.
Released: June 25, 2026