His Majesty the King v. Yousaf Sheikh, 2026 ONSC 2186

CITATION: R. v. Yousaf SHEIKH, 2026 ONSC 2186

COURT FILE NO.: 24-30000506-0000

DATE: 20260413

ONTARIO

SUPERIOR COURT OF JUSTICE

BETWEEN:

HIS MAJESTY THE KING

Respondent

– and –

YOUSAF SHEIKH

Applicant

Jake Humphrey for the Crown

Uma Kancharla for the Applicant

HEARD: January 27, 2026

REASONS FOR SENTENCE

WASSENAAR J:

Background and allegations

1Mr. Sheikh faced a nine count indictment in relation to an incident on November 29, 2022. It was alleged that Mr. Sheikh was in a car with two other people, Ms. Mallory Walia and Mr. Ameen Jazei. The Crown alleged that Mr. Sheikh fired a firearm, injuring Ms. Walia and Mr. Jazei. The evidence included a surveillance video that showed a white Porshe occupied by Mr. Jazei and Ms. Walia crash into a parked car. Multiple shots can be heard on the video, and a person is seen exiting the Porsche from the front passenger door. Mr. Sheikh could not be excluded from DNA found on the front passenger air bag, which deployed when the Porsche crashed. Mr. Jazei could not be excluded as a contributor to DNA found on a 9 mm Glock pistol found on the floor near the front passenger seat. Neither Mr. Sheikh nor Mr. Jazei could be excluded as a contributor to DNA on a 9 mm gun found on the ground near the front passenger side of the Porsche. Mr. Sheikh was also linked to the incident through a distinctive diamond encrusted chain. Mr. Jazei and Ms. Walia were taken to hospital that evening for their injuries. The person believed to be the shooter can be seen in another surveillance video running away. The main issues at trial were identification and self-defence.

2On July 31, 2025, a jury convicted on all eight counts that the Crown pursued:

Counts 1 and 2, the attempted murder of Mr. Jazei (1) and of Ms. Walia (2)

Counts 3 and 4, discharging a firearm with the intent to endanger the life of Mr. Jazei (3) and of Ms. Walia (4)

Counts 5 and 6, point firearm without lawful excuse at Mr. Jazei (5) and at Ms. Walia (6)

Count 8, occupy motor vehicle knowing that there was a prohibited or restricted firearm in it

Count 9, possess a loaded prohibited or restricted firearm without authorization or license and registration

3Sentencing submissions were scheduled for August 21, 2025 but they did not proceed until January 27, 2026. In the interim, two mistrial applications were brought and dismissed.

Factual Basis for Sentencing

4In R. v. Ferguson, 2008 SCC 6, [2008] 1 S.C.R. 96, at paras. 17-18, McLachlin C.J. summarized the applicable principles where a sentencing judge must make factual findings to facilitate sentencing following a jury trial. First, I am bound by the express and implied factual implications of the jury’s verdict. I must not accept as fact any evidence consistent only with a verdict rejected by the jury. Second, when the factual implications of the jury’s verdict are ambiguous, I should not try to follow the jury’s logical process. Instead, I should come to my own independent determination of the relevant facts. I also note that aggravating facts must be proven beyond a reasonable doubt. Mitigating facts need only be proven on a balance of probabilities.

5Prior to sentencing submissions, a Gardiner hearing was held: R. v. Gardiner, 1982 30 (SCC), [1982] 2 S.C.R. 368. At the Gardiner hearing, the defence called two police officers and the accused. Detective Parmar spoke to Mr. Jazei at the hospital on November 30, 2022. Detective Johnston examined bullet defects and bullet trajectory in the Porsche. Two affidavits of the accused were made exhibits. One was dated January 27, 2026 (sentencing Exhibit 2) and the other was from one of the mistrial applications and dated November 10, 2025 (sentencing Exhibit 13). The defence also filed the October 21, 2025 affidavit of Bushra Naba Islam from the mistrial (sentencing Exhibit 14).

6I will apply the principles from R. v. Ferguson set out above when determining the facts for the purpose of sentencing.

The Offences

7It is implicit in the jury’s verdict that Mr. Sheikh intended to kill two people, Mr. Jazei and Ms. Walia. The jury rejected the defence position that he was acting in self-defence.

8Based on the evidence at trial and the Gardiner hearing, I find that Mr. Sheikh fired multiple shots while he was inside the car with the two victims. I also find that this was an arranged event, in that Mr. Sheikh arrived with a gun, multiple cars were present near the scene, and a car was readily available for Mr. Sheikh to make a quick exit. It is not clear exactly what Mr. Sheikh’s purpose was in entering the Porsche that night, but I find that he was armed when he entered the car.

9There was evidence on the Gardiner hearing that Mr. Sheikh sustained an injury during the altercation. In Mr. Sheikh’s November 10, 2025 affidavit he stated that he “sustained a gunshot wound on November 29, 2022 in the Porsche.” In Mr. Sheikh’s January 27, 2026 affidavit he stated that he suffered a bullet graze wound on November 29, 2022 from “a deliberate shot aimed at me.” On cross-examination he agreed that he did not say who shot him. He went on to explain that he did not know the person who shot him. He was not willing to provide any more details. He said it was not possible that he shot himself. He said a 9 mm bullet could not have caused the wound that he had on his arm. He went on to explain that a gun was pointed at him and it went off, so the wound had to be from that and could not be from him. Mr. Sheikh stated in his second affidavit that the “bullet graze wound” caused him pain. His first affidavit and the affidavit of his former girlfriend, Ms. Islam, discussed the treatment of the injury. There were also photos and a video of the injury, which showed a wound on Mr. Sheikh’s arm and some marks on his hand. The defence also filed a report from Dr. Steven White. Dr. White stated that the wound on the left forearm was consistent with a graze gunshot wound, and there were signs of tissue injury and healing. Dr. White also noted multiple abrasions on the left hand and left wrist, but it was not possible to determine their cause.

10I have considered the evidence at trial and at the Gardiner hearing, including the evidence referred to above as well as:

• the video of the shooting (trial Exhibit 2);

• the portion of the statement (sentencing Exhibit 16) relied on by counsel during submissions in which Mr. Jazei said “ended up letting off some”;

• the trajectory evidence of Officer Johnston;

• evidence about damage to the Porsche after the shooting;

• evidence about firearms, projectiles and casings;

• Mr. Jazei’s evidence at trial that he had a firearm on November 29, 2022, possibly more than one;

• the DNA evidence;

• evidence at trial that Ms. Walia had ammunition in her purse, and her criminal record;

• evidence at trial, including the Agreed Statement of Fact (trial Exhibit 21), about the injuries sustained by Mr. Jazei and Ms. Walia.

11I am unable to determine, on a balance of probabilities, the precise cause of the injury to Mr. Sheikh’s arm. However, I do find, on a balance of probabilities, that the injury occurred during the altercation on November 29, 2022. I would not characterize the injury as serious.

Mr. Sheikh

12Mr. Sheikh did not testify at trial, but he did testify at the Gardiner hearing and provided two affidavits. I was also provided with a pre-sentence report (“PSR”) prepared for his July 2025 sentencing on a robbery, and a letter of support from his sister on behalf of his family.

13Mr. Sheikh is now 24 years old and was 20 – almost 21 – at the time of the offences. He was born in Toronto; his parents are from Pakistan. His father arrived in Canada in 1997 and his mother in 2000. Mr. Shiekh is the youngest of 5 siblings. One brother works in IT, the other is a bus driver, and his two sisters are raising their families. Mr. Shiekh is close with both of his parents.

14Mr. Sheikh lived with his family at Wellesley and Parliament until he was 19. The family then moved to Courtice, Ontario and lived in a home owned by his older brother. Mr Sheikh then moved to Oakville where he lived in a condominium with his mother. Mr. Sheikh described the neighbourhood where he grew up as a bad area, but other family members were less negative about it. Mr. Sheikh’s father worked as a taxi driver. The family was not well off, but the PSR indicates that they had what they needed. Mr. Sheikh’s affidavit refers to “difficult socioeconomic circumstances”.

15Mr. Sheikh said about four of his friends died when he was growing up. He finished high school in 2019. The PSR quotes him as describing his academic performance as, “[j]ust above passing, I never paid too much attention, staying above water.” His January 2026 affidavit states that despite the challenges of his upbringing, “I remained committed to my education and worked diligently in my academic pursuits.”

16In the PSR, Mr. Sheikh was quoted as saying that his oldest sister, who was like a second mother, was “always pushing me to do IT”. In his affidavit, Mr. Sheikh stated that “[t]hrough perseverance, I obtained employment in the field of information technology, a field in which I took pride and hoped to establish a long term career”. Mr. Sheikh went to a private college for IT in 2021 for seven months. He did two months of an online cybersecurity course. At age 21 he got a job in IT at an insurance company, making $65,000 a year. He worked for a year before he was arrested. In his affidavit, he indicated his desire to resume employment in IT. He intends to pursue further education and training upon release.

17In his affidavit, Mr. Sheikh spoke of his deep respect for his parents and his Muslim faith. He also noted that his parents have experienced health challenges, and he wanted to support and care for them.

18In exploring his experiences of racism and discrimination and how he’s been stereotyped, the PSR stated that Mr. Sheikh felt discriminated against and felt various stereotypes in varying situations. For example, when in school, there may have been some comments about his religion.

19There were no indications that Mr. Sheikh had any substance abuse issues. There were no indications of violence in the home when he was growing up.

20The PSR writer described Mr. Sheikh as cooperative, respectful and engaged.

21Mr. Sheikh’s sister described him as caring and responsible, religious and grounded in strong values. She says he is a devoted son, brother and uncle. His family is fully committed to supporting him upon release. They believe he can grow and move forward positively.

22Mr. Sheikh did not have a criminal record prior to November 2022. He was arrested on March 6, 2023 and released on bail on April 21, 2023. On May 31, 2024 his bail terms were varied to permit him to be out of his home with his surety. On June 14, 2024 Mr. Sheikh opened the driver’s side door of a car, told the driver to get out of the car or he would shoot him, and forced his way into the vehicle, causing the driver to exit. Mr. Sheikh drove away and collided with two other cars but did not stop. He drove erratically along Front Street until his car became inoperable. He tried to enter another car but did not succeed and was arrested: R. v. Sheikh, 2025 ONCJ 551, at paras. 6-10. Mr. Sheikh pleaded guilty on May 20, 2025, his sentencing hearing took place on September 19, 2025, and he was sentenced on October 21, 2025: R. v. Sheikh, 2025 ONCJ 551.

23In his allocution after his attempted murder trial, Mr. Sheikh said that he was sorry for everything that happened. In his allocution and his affidavit, Mr. Sheikh said he wanted to rebuild his life in a positive, responsible, and productive manner.

Positions of Counsel

24The Crown took the position that Mr. Sheikh should receive two life sentences for the two counts of attempted murder, to run concurrently. The Crown submitted that conditional stays should be entered on counts 3, 4, 5 and 6, and that Mr. Sheikh should receive three to five years concurrent on count 8, and four to six years concurrent on count 9.

25Ms. Kancharla took the position that Mr. Sheikh should receive a six-year sentence on the attempted murder offences, and one year each, concurrent, on counts 8 and 9.

Law and Analysis

26I accept the position of both counsel that counts 3, 4, 5 and 6 should be stayed pursuant to R. v. Kienapple, 1974 14 (SCC), [1975] 1 SCR 729. The main focus of my analysis will be on the two counts of attempted murder. I will address counts 8 and 9 more specifically near the end of my analysis.

Principles of Sentencing

27My task is to impose a just sentence tailored to this individual offender and his specific offences, in accordance with the principles and objectives laid out in the Criminal Code, R.S.C. 1985, c. C-46: R. v. Lacasse, 2015 SCC 64, [2015] 3 S.C.R. 1089, at paras. 11, 56. Thus, the starting point for my analysis is the sentencing principles set out in ss. 718, 718.1 and 718.2. The fundamental purpose of sentencing is “to protect society and to contribute, along with crime prevention initiatives, to respect for the law and the maintenance of a just, peaceful and safe society by imposing just sanctions”: s. 718. That sanction should have one or more of the following objectives: denunciation, deterrence, protection of society, rehabilitation of the offender, reparation to the victim, the promotion of a sense of responsibility in the offender, and acknowledgement of the harm caused to the victim or community: R. v. Sheppard, 2025 SCC 29, at para. 71.

28Proportionality is the “loadstar” that guides the sentencing process: R. v. Morris, 2021 ONCA 680, 159 O.R. (3d) 641, at para. 59; R. v. Lacasse, at para. 12. What is regarded as a proportionate sentence depends on “society’s current understanding and awareness of the gravity of a particular offence and blameworthiness of particular offenders”: R. v. Friesen, 2020 SCC 9, [2020] 1 SCR 424, at para. 35; R. v. Sheppard, at para. 68. Parity, totality and restraint are also guiding principles: s. 718.2. Parity is an expression of proportionality: R. v. Friesen, at para. 32; R. v. Sheppard, at paras. 69-70. Denunciation and deterrence are paramount principles when determining a sentence for a firearm offence: R. v. Smickle, 2014 ONCA 49, 306 C.C.C. (3d) 351, at para. 18; R. v. Graham, 2018 ONSC 6817 at para. 36, aff’d 2020 ONCA 692, 474 C.R.R. (2d) 137.

The Range of Sentence for Attempted Murder

29In R. v. McArthur (2004), 2004 8759 (ON CA), 182 CCC (3d) 230 (ON CA) at para. 47 Justice Doherty stated:

Under our law, a person can only be convicted of attempted murder if he or she intended to kill. The moral culpability of the attempted murderer is at least equal to that of a murderer. He or she avoids a murder conviction and the automatic sentence of life imprisonment not because of any mitigating factor, but because through good fortune, the victim was not killed.

30He then noted that a conviction for attempted murder will almost inevitably result in a lengthy penitentiary term.

31Attempted murder cases that have further guided my understanding of the appropriate range include the following:

R. v. Mohamed, 2014 ONCA 814: The Court of Appeal upheld a 13-year sentence for attempted murder and breaches of firearms prohibition orders and recognizance orders. The appellant was a youthful offender, and this would be his first custodial sentence. The appellant attempted to kill a security guard who had apprehended his friend. He fired several shots. The court stressed the importance of denunciation and deterrence in cases of gun use in a public place.

R. v. Adan, 2019 ONCA 709: The Court of Appeal upheld an 11-year sentence for attempted murder. The appellant brought a gun to the scene, fired multiple shots, and caused serious injuries. The appellant was 21 at the time of the offence and 24 at the time of sentencing. He was a first offender at the time of the offence, but had been convicted of a firearm offence prior to sentencing.

R. v. Abdullahi, 2022 ONSC 543: The offender pleaded guilty to shooting the victim multiple times. Mr. Abdullahi was 23 at the time of the offence, and a first offender. The victim was seriously injured. The Crown sought an 18 year sentence, the defence 10 years. The trial judge analyzed several cases, and concluded that “[t]he range of sentence for the offence of attempted murder with a firearm in circumstances where the offence takes place in a crowded public area is from 10 years to life depending on the circumstances of the offender”: at para. 45. The judge imposed a 14-year sentence, before considering the conditions during pre-sentence custody.

R. v. Aiken, 2024 ONCA 326: The Court of Appeal upheld a 15-year sentence for discharge firearm with intent to wound or prevent arrest and attempted murder. The appellant fired multiple shots during an encounter with two police officers. The appellant sustained significant injuries: seven gunshot wounds and a dog bite. The sentence was reduced by nine years and seven months for presentence custody.

32Many of the cases relied on by the Crown in arguing for a life sentence were considerably more aggravating than the case at bar. For example, in R. v. Brown, 2009 ONCA 563, 251 O.A.C. 264 the victim was confined to a wheelchair, paralyzed from the waist down, and the offence occurred in a location where other citizens, including children, were present and at potential risk. The Court of Appeal upheld the life sentence, noting the serious and growing problem of gun violence in Toronto. While the circumstances in Brown are different, the problem of gun violence remains a pressing societal concern.

Aggravating and Mitigating Factors

33Aggravating factors include the following:

• There were two victims of attempted murder.

• Mr. Sheikh used a firearm in the commission of the offences, inside a vehicle.

• The offences occurred in a public place.

• There was an aspect of planning leading up to the incident.

• While Mr. Sheikh must be sentenced as a first offender, the robbery offence committed while on bail is relevant to his rehabilitative prospects.

34Some of these factors require elaboration.

35Both victims were injured, but not nearly as severely as the victims in some of the case law cited before me. Although neither victim filed a victim impact statement, I can infer that there would be psychological damage from this incident: R. v. Bertrand Marchand, 2023 SCC 26 at para. 75-76; R. v. May, 2011 ONCA 74 at para. 9. Multiple shots were fired, the victims’ SUV crashed into another vehicle, and the victims’ emotional reactions can be heard on the security video.

36While the offences occurred in a public place, it was in a semi-industrial area in the evening. The incident took place between 7:00 and 8:00 p.m. and the security videos do not show much activity at that time. However, there were numerous cars on the street and an employee came out of a nearby business and called for assistance after the Porsche crashed.

37Mitigating factors include the following:

• Mr. Sheikh is now 24 years old and was almost 21 at the time of the offences.

• Mr. Sheikh had no criminal record prior to the commission of this offence.

• Mr. Shiekh experienced discrimination growing up as a racialized person in Toronto.

• Mr. Sheikh received an injury to his arm during the altercation.

• Mr. Sheikh spent time on bail.

• Mr. Sheikh experienced particularly punitive pretrial incarceration.

• Mr. Sheikh was injured while in custody.

• The strong family support that Mr. Sheikh enjoys increases the prospect of rehabilitation.

38Some of these factors require elaboration.

39Sentencing a youthful first offender requires me to exercise restraint, prioritize rehabilitation, and account for Mr. Sheikh’s immaturity at the time of the offences: R. v. Habib, 2024 ONCA 830, 99 C.R. (7th) 110, at paras. 7, 30-36. I pause here to note that R. v. Habib also addresses the need to consider family consequences: paras. 41-50. Ms. Kancharla makes that argument in this case. While Mr. Sheikh noted his parents’ health challenges and his desire to care for them, that factor has limited relevance in the case at bar. In Habib, the appellant had two ailing parents and three younger siblings, and the family suffered significant financial and health impacts from the appellant’s incarceration. While family separation consequences are not limited to situations of dependency, there is minimal evidence to support this as a mitigating factor in this case. To the contrary, Mr. Sheikh has older siblings who are all productive members of society and there is no indication that they cannot assist their parents.

40I consider Mr. Shiekh’s youth in combination with the evidence he provided about his experiences as a racialized person growing up in Toronto. Although addressing young offenders, I rely on the Supreme Court of Canada’s analysis in R. v. I.M., 2025 SCC 23 regarding the interplay between youth, disadvantage and social context: at paras. 162-167.

41I have included the injury to Mr. Sheikh’s arm during the altercation as a mitigating factor, although it may more properly be characterized as a collateral consequence. The strength of this injury as a mitigating factor is somewhat muted, particularly since this was not a very serious injury: R. v. Aiken, 2024 ONCA 326 at para. 13.

42Mr. Sheikh spent about 14 months on bail, from April 21, 2023 to June 14, 2024. He described his bail conditions as extremely restrictive and said they had a significant psychological impact on him. He struggled with feelings of isolation and loss of purpose. He says that on one occasion he was unable to obtain emergency medical services when he was feeling physically unwell. When cross-examined on his affidavit, Mr. Sheikh said that his time on bail was spent with family, playing video games and watching movies.

43In R. v. Prindle, 2025 ONCA 386, at paras. 12-13 the Court of Appeal for Ontario summarized the approach to time spent on bail as a mitigating factor. Considerations include “the amount of time spent subject to strict bail conditions; how stringent the bail terms were; their impact on the offender’s liberty; and the ability of the offender to carry on normal relationships, employment, and activity while on bail”. In my view the bail conditions were punitive enough to be “akin to punishment” and are therefore capable of providing some mitigation.

44My consideration of conditions in custody as a mitigating factor follows the analysis in R. v. Marshall, 2021 ONCA 344, at paras. 50-53. Mr. Sheikh says that during his time in custody there were frequent lockdowns, chronic overcrowding, triple bunking and limited access to showers, phone calls and yard time. His affidavit explains that the conditions caused significant emotional distress and anxiety. The conditions deeply affected his dignity, and made it difficult for him to maintain his religious obligations. Overall, there was a serious impact on his mental health. In addition to Mr. Sheikh’s affidavit, the defence provided records from the institution (sentencing Exhibit 8). They show 80 days of full and partial lockdowns from June 14, 2025 to January 19, 2026, and 52 days of triple bunking from June 30, 2025 to September 29, 2025. There is some overlap with the time that was considered at his sentencing on the robbery: see R. v. Sheikh, 2025 ONCJ 551, at paras. 55-71. Given their regularity, I am prepared to infer that these deplorable conditions continued to some degree from the date of sentencing submissions on January 27, 2026 until the date I am delivering my reasons for sentence, April 13, 2026.

45I have considered the injuries Mr. Sheikh experienced in custody as a separate consideration from the conditions in custody. Mr. Sheikh was injured at the Toronto South Detention Centre during his trial. I was able to observe injuries during the trial. In his affidavit, Mr. Sheikh stated that on July 16, 2025 he was “viciously attacked” by another inmate on the way to court. An inmate punched him in the face yelling “Rat” and “Snitch”. He suffered a split lip, which he said caused “a lot of pain.” Later that day, Mr. Sheikh was again assaulted by an inmate, this time in his cell. His glasses were broken and he was cut above the eye, which he described as “painful”. These assaults compounded the “emotional strain, vulnerability, degradation [and] isolation” he was already experiencing at the jail. Although the injuries Mr. Sheikh sustained are better characterized as part of his “personal circumstances”, rather than as a mitigating factor, I have included them in this part of my analysis: R. v. Suter, 2018 SCC 34, [2018] 2 S.C.R. 496, at paras. 45-59; R. v. Nasogaluak, 2010 SCC 6, [2010] 1 S.C.R. 206.

A fit sentence for two counts of attempted murder

46Considering the circumstances of the two attempted murder offences and the circumstances of this offender, in my view a fit sentence is 14 years incarceration.

Counts 8 and 9

47The conviction on count 8 was for occupying a motor vehicle knowing that there was a prohibited or restricted firearm in it. The conviction on count 9 was for possessing a loaded prohibited or restricted firearm without authorization or license and registration.

48The Crown submitted that Mr. Sheikh should receive three to five years concurrent on count 8, and four to six years concurrent on count 9. Ms. Kancharla took the position that Mr. Sheikh should receive one year each, concurrent, on counts 8 and 9.

49An appropriate sentence for count 8 is three years: R. v. Derby, 2023 ONCA 499; R. v. Sitladeen, 2024 ONSC 4244, at para. 57; R. v. Hernandez-Viera, 2022 ONSC 3776, at para. 37.

50An appropriate sentence for count 9 is four years: R. v. Watts & Bartley, 2024 ONSC 4501, at para. 45.

51The sentences for counts 8 and 9 shall run concurrent to each other and concurrent to the sentences for attempted murder.

Credit for pre-trial custody

52Some of the time Mr. Sheikh spent in pre-sentence custody was credited on his robbery sentence: R. v. Sheikh, 2025 ONCJ 551, at paras. 55-59, 71-75. I have made the following calculation for the period from his March 6, 2023 arrest to the date scheduled for delivering these reasons, April 13, 2026:

Time period

Number of real days and credit

Explanation

March 6 arrest to April 21, 2023 release on bail

47 real days at 1.5 = 70.5

Only incarcerated on attempted murder

June 14, 2024 arrest on robbery to October 21, 2025 sentencing for robbery: 495 Unused portion leftover from robbery: 495-446=49

49 real days at 1.5 = 73.5

Pre-sentence custody not used on robbery

October 21, 2025 to April 13, 2026

175 real days at 1.5 = 262.5

Pre-sentence custody after sentencing on robbery

TOTAL CREDIT

406.5

53The 14-year sentence should be reduced by one year and 42 days. The sentence is therefore 12 years, 10 months and 23 days.

Ancillary orders

54Ms. Kancharla was content with the ancillary orders suggested by the Crown. I therefore order:

• Lifetime weapons prohibition pursuant to s. 109 of the Criminal Code;

• DNA order pursuant to s. 487.051 of the Criminal Code;

• Non-communication order in relation to Ameen Jazei, Mallory Walia, or any member of their immediate family pursuant to s. 743.21 of the Criminal Code

The Honourable Justice B. Wassenaar

Released: April 13, 2026

CITATION: R. v. Yousaf SHEIKH, 2025 ONSC 2186