CITATION: R v. Bailey, 2026 ONSC 4363

COURT FILE NO.: CR-11-846-00SR

DATE: 2026-07-27

ONTARIO

SUPERIOR COURT OF JUSTICE

B E T W E E N:

HIS MAJESTY THE KING

T. Powell, for the Crown

Crown

• and -

SHEVON BAILEY

B. Vandebeek, and A. Youssef, for the Defence

Defendant

HEARD: In-Writing

RULING ON AN APPLICATION PURSUANT TO s. 745.6 OF THE CRIMINAL CODE

Mirza J.

OVERVIEW

1On November 12, 2009, the Applicant, Mr. Shevon Bailey, along with two associates, invaded Mr. Kalogerakis’ home intending to rob him. They were armed with a rifle. During the robbery, Mr. Kalogerakis was shot and killed. His elderly mother was bound and tied. According to the prosecution, Mr. Bailey was the shooter.

2After the Court of Appeal ordered a retrial, Mr. Bailey was convicted of first degree murder on October 5, 2017.

3Mr. Bailey seeks a reduction or termination of the mandatory 25-year parole ineligibility term imposed following his conviction for first degree murder pursuant to the requirements in s. 745.61(5) of the Criminal Code.

4Mr. Bailey is 38 years old and has served over 16 years in custody. He maintains his innocence in relation to the conviction.

5On behalf of the Associate Chief Justice (ACJ) McWatt, I have been designated to screen the application under s. 745.61(1) of the Criminal Code. Should I conclude that Mr. Bailey has justified a hearing before a jury, the ACJ has also designated me, under s. 745.61(5), to empanel a jury to hear the application.

6To be clear, this is the preliminary screening as to whether a jury should hear and decide the application. If successful at this stage, the applicant proceeds to the second stage, where they present their case before a 12-person jury to decide the actual application.

7If there is a unanimous vote that the number of years of imprisonment without eligibility for parole ought to be reduced, the jury may (by a vote of not less than two thirds): (a) substitute a lesser number of years of imprisonment without eligibility for parole; or (b) terminate the ineligibility for parole.

8It is important to understand that this is an application regarding a reduction of parole ineligibility below the otherwise mandatory 25 years. It is not an application to reduce the sentence. This is in part why it is colloquially referred to as a faint hope application.

9Even if Mr. Bailey was successful at the first stage, and at stage two, he would still have to convince a parole board to release him on conditions that are monitored. A life sentence would remain.

10For the reasons that follow, I find that the Applicant has not demonstrated on the balance of probabilities that there is a reasonable prospect that a unanimous jury would find that his parole eligibility ought to be reduced. As a result, the application is dismissed.

LAW

Screening Test

11The judicial screening threshold for an offender that committed an offence between January 9, 1997, to December 2, 2011, is whether there is a “reasonable prospect” that the application will succeed: R. v. Liu, 2022 ONCA 460; R. v. Dell, 2022 ONCA 460 at para. 102; R. v. Joseph, 2026 ONCA 317 at paras. 26-34.

12This requires the appointed screening judge to decide whether the applicant has demonstrated on a balance of probabilities that there is a reasonable prospect of success that a jury would unanimously vote to reduce his period of parole ineligibility. If I am so satisfied, the application proceeds to a hearing before a jury empaneled for that purpose, in accordance with s. 745.61(5) of the Criminal Code: R. v. Atkins, 2022 ONCA 709, at para. 2.

13In R. v. Al-Shammari, 2022 ONSC 4113, at paras 12-13, Pomerance J. explained the "reasonable prospect" of success threshold test:

12[I]t asks whether it is reasonable to expect that a jury might reduce the parole ineligibility period. This need not be the only rational or reasonable outcome available on the record. If it falls within a range of reasonable outcomes, it qualifies as a reasonable prospect of success. Where an offender can point to rehabilitative progress, remorse, maturation, and a commitment to pursuing a pro-social lifestyle, those factors will weigh in favour of a jury hearing

13To be clear, the screening judge is not predicting what a jury will actually do. That requires a level of prescience that no judge can claim: see R. v. Jenkins, 2014 ONSC 3223, quoted with approval in Dell. More accurately, the screening judge is assessing whether a jury could grant clemency, based on the evidence of rehabilitation.

14At this screening stage, the focus is an assessment of the offender’s progress during the over 15 years spent in jail: R. v. Morrisson, 2016 ONSC 5036 at para. 38; Atkins, at para. 7.

15The Court of Appeal in Dell at para. 20 explained the purpose of the process:

20The judicial screening criterion established in 1996 was judicially interpreted as setting a relatively low bar intended to prevent applications being brought before a jury that had no realistic chance of success. The purpose of the provision was twofold. First, to save friends and relatives of the victims of the murders the needless pain and anguish of going through a “faint hope” hearing before a jury when the applicant had no realistic chance of success. Second, the screening process was intended to avoid wasting jurors’ time and judicial resources on hopeless applications: see R. v. Jenkins, 2014 ONSC 3223, 310 C.C.C. (3d) 248, at paras. 20-22; R. v. Phillips, 2011 ONSC 1914, at paras. 6-9, aff’d 2012 ONCA 54, 288 O.A.C. 351, at paras. 6-7; R. v. Rochon, 2011 ONSC 5061, at paras. 6-7; R. v. Oczko, 2012 ABQB 121, 535 A.R. 59, at paras. 4-13.

Statutory Factors

16Determining the threshold question is based on an assessment of the factors in ss. 745.61(2) and 745.63(1):

(a) the character of the applicant;

(b) the applicant’s conduct while serving the sentence;

(c) the nature of the offence for which the applicant was convicted;

(d) any information provided by a victim at the time of the imposition of sentence or at the time of the hearing under these sections; and

(e) any other matters that the judge considers relevant in the circumstances.

17All of the factors are to be considered, though each factor is not necessarily given the same weight. It depends on the total circumstances and the evidence: Morrisson, at para. 36.

Relevant Factors Reviewed

The Offences

18The Applicant’s first-degree murder conviction was based on s. 231(5)(e) of the Criminal Code, R.S.C. 1985, c. C-46, committing murder while committing or attempting to commit forcible confinement.

19The following summary is from Court of Appeal Decision, R. v. Bailey, 2022 ONCA 502, dismissing the appeal.

20On Thursday, November 12, 2009, shortly before 1:00 a.m., three young men entered the home of George Kalogerakis intending to rob him.

21They believed that he had significant cash inside of his home.

22During the robbery, the victim, insisted he had no money.

23The victim’s mother heard a struggle downstairs and her son call out to call 911. Before she could do so, a masked man with a long gun came upstairs, pushed her downstairs with the gun, and ordered her to sit on the bottom of the stairs near the foyer.

24There were three men, whom the mother described by height and clothing. The tallest and middle height men wore bandanas over their faces and gloves. The shortest, also described as the youngest, wore a hood with nothing covering his face. The Crown’s position was that the tallest man was the Appellant.

25The tallest man ordered the shortest man to tie up the mother. The shortest man taped her wrists and ankles and sat with her in the living room holding a knife. He took her car keys and wallet from her purse. The younger man held her at knife point throughout the incident.

26The tallest man went back upstairs, leaving the middle height man with the victim. Forensic evidence indicated that at some point, the victim was shot in the arm in the foyer. That was not the fatal shot.

27After the tallest man came back downstairs, he and the middle height man dragged the victim to the basement. After a short time, the mother heard a shot.

28By the time the two robbers took the victim to the basement, the gun had already been used. Using it again would not have been a surprise. And if there was money on the premises, the victim would certainly have given it up by the time he was taken, injured and bound with duct tape, to the basement. Logically, there was only one purpose to take the victim down, out of sight of the mother, and that was to kill him so that he could not identify the perpetrators.

29No one testified as to what occurred in the basement. The victim was found bound, and from the blood spatter and position of the body, it was determined that he would have been sitting, kneeling or crouching when he was shot.

30The robbers then came back upstairs. The mother originally testified at the first trial that the tallest man passed the gun to the middle height man after he brought her downstairs and before they took the victim to the basement. At the second trial, the mother stated that she did not remember who had the gun when the two men went down to the basement, but that the tallest man had the gun when they came back upstairs. Once they returned upstairs, they unplugged the kitchen phone and left the house together, with the tallest one pointing the gun at the mother while he backed out the front door.

31In the days leading to the home invasion and murder, Mr. Bailey communicated with associates about the plan to obtain a gun and enter the residence. They knew that the victim’s mother would be home.

32In the text messages that preceded the robbery, the Applicant said that he would bring a 22-calibre gun.

33The morning before the robbery, the Applicant and another person knocked on the door of the victim’s home around 7:00 a.m., after he had left for work, and spoke to his mother through the door. The Applicant texted the victim’s neighbour later that he had tried that morning and would go back tomorrow.

34At the first trial, Mr. Bailey testified that he had backed out of the plan. At his second trial, he did not testify. His position was that he was not one of the robbers. He had been involved in the planning but backed out after attending the victim’s residence on the morning before the robbery. His exculpatory police statement was tendered by the Crown. If the jury rejected that position, then the issue was the extent of the Applicant’s liability. Mr. Bailey conceded on appeal that all three of the robbers were guilty of manslaughter and that if he was one of the robbers, he was not the shortest man who stayed on the ground floor during the robbery.

35The Crown’s primary position at trial was that the Applicant was the shooter. However, if the jury was not satisfied that the Applicant was the shooter, the Crown’s secondary position was that the Applicant was a party to the offence of murder and that he could be found liable either as having aided the shooter under s. 21(1)(b) of the Code or as having formed a common intention with the shooter under s. s. 21(2) of the Code.

36If the Applicant was the actual shooter, then the basis for first degree murder was essentially indisputable. If the Applicant was not the shooter, but he was a party to the murder, then the jury had to determine whether, in accordance with R. v. Harbottle, 1993 CanLII 71 (SCC), [1993] 3 S.C.R. 306, the Applicant played “a very active role – usually a physical role – in the killing”, and that his action formed “an essential, substantial and integral part of the killing of the victim”: at p. 324.

Impact on the Victims

37The victims updated impact statement letters from December 2025 have been carefully considered. They are detailed and compelling.

38I will summarize the letters. I recognize that a written summary cannot reasonably capture the full weight of their experiences and associated pain, but they are duly factored.

39I pause here to note that I confirmed with the Crown, who was also trial counsel, that victim impact statements from 2017 were not available despite the Crown’s review of the file. There is no indication on the indictment that any were filed.

40In their letters, the family members explain how the home invasion and murder of Mr. Kalogerakis have left them feeling insecure in their community and homes, with a constant vigilance for their safety. The nature of the offence was highly intrusive to their personal security and undermined their trust in humanity. They live with grief, loss, and fear for their safety. Their respective letters individually and in combination inform with clarity to the gravity and aggravating nature of the offences.

41The mother, Ms. Kalogerakis, was also a victim of violence on that tragic night. I recognize that that she has been forever changed, and her mental health has suffered severely due to the extraordinary stress.

42Both of Mr. Kalogerakis’ sisters discuss that they cherished their relationship with their brother and describe his important role in the family. They endure anguish and trauma in their daily lives.

43Both brothers-in-law explain how this murder has harmed their wives, mother-in-law, children, altering their personal circumstances in ways that have caused remarkable hardship and suffering.

44The victim’s two nieces and two nephews each express the sorrow from the loss of their uncle who was a positive and loving force in their life.

45Many of the family members have taken therapy but still are overcome by grief, frustration, and anger at how the victim was wrongly taken from them and in this most horrendous way.

Applicant’s Character

Criminal Antecedents

46Mr. Bailey has three prior convictions on his criminal record, including convictions for assault and possession of a weapon in 2009, and assault in 2011. He had not served jail time before, receiving non-custodial dispositions and probation and weapons prohibition order.

47His 2011 conditional discharge was from a January 2009 incident, where he pushed and choked his girlfriend.

48His 2009 conviction was from an incident that followed the January 2009 assault. In March of 2009, while on a release, he choked his mother, threw her on the bed, and punched her. After his stepfather intervened, the Applicant armed himself with a knife.

Personal History Background

49Mr. Bailey was born in Clarendon, Jamaica on May 23, 1988. He is presently 37 years old.

50In terms of education, he finished grade 11. After his conviction, the institution conducted a learning disability screening to assess his educational background. It said he was at risk for a learning disability but there is no diagnosis.

51However, Mr. Bailey was motivated to complete high school and earned his degree in 2019.

52Before his arrest, Mr. Bailey worked as a teenager at Canada's Wonderland; and UPS in the evenings while he was still in school. He worked at a restaurant in the kitchen through his high school's co-op program. Later, he worked in the Canadian Tire Warehouses full time. He continued working at the Warehouses until about a year before his arrest. At the time of his arrest, he was not working.

Family

53Mr. Bailey was raised by his parents in Jamaica with his younger sister, Shantae, until he was six or seven years old. His parents separated around this time and his mother moved to Canada while his father moved to the United States.

54Mr. Bailey lived with different family members in Jamaica before he and his sister moved to Canada to live with their mother in 1998. Mr. Bailey was 10 years old.

55In Canada, Mr. Bailey was raised primarily by his mother, who worked hard to support Mr. Bailey and his sister. Although his father lived in the United States, they stayed in contact, and Mr. Bailey would travel to visit him. In addition to his sister Shantae, with whom he shares both parents, he has a younger sister on his mother’s side, Fantasia, and a younger brother on his father’s side, Brandon. He describes close relationships with all his siblings growing up, particularly with his sisters who lived in Canada with him.

56His sister, Shantae, his mother, and his father wrote in support of the application that he has grown and matured, and that they are willing to support his reintegration if released.

57While incarcerated, Mr. Bailey has maintained a positive support network.

58Scott Bruce, a correctional officer at Collins Bay Institution, provided a letter of support that comments on Mr. Bailey’s improvement since 2019, taking full-time education and programs, while conducting himself respectfully. He said he has worked with him directly since 2023.

59Mr. Da Costa, another correctional officer at Collins Bay Institution, describes that he has taken rehabilitation programs and commitment to being a respectful and positive contributing member of the community.

Social Context

60In a July 2025 institutional report by his parole officer, it states that under the heading of Black social history, that he grew up in a high crime area and had negative peer association, which were a precursor to his involvement in the crime.

61He reported being subject to racial profiling by law enforcement before his incarceration.

62He said that he has experienced racism more in jail than in the community. However, specific incidents are not described.

Employment in Jail

63Mr. Bailey worked various jobs at different institutions, such as a cleaner, cook, and server. While at Millhaven, he focused on being a range representative. This required him to be a mediator and advocate for others.

Education in Jail

64In addition to completing his OSSD in 2019, he took a course on organizational behaviour at Northern College.

65In the voluntary transfer application from Millhaven Max to BCI, the author stated (p. 101 pdf):

Bailey has been participating in educational upgrading, and he only requires 1.5 senior level credits in order to earn his Ontario Secondary School Diploma (OSSD). Reports from the school indicate that BAILEY regularly attends school and remains in his designated classroom. He remains on task without reminders, works quietly and efficiently, willingly participates in classroom activities (i.e. discussions, debates, group activities) and consistently meets the expectations as determined by the teacher. BAILEY is described as polite and respectful in communications with others and responds positively to the advice, suggestions and direction of staff.

Rehabilitation Programs

66In 2014, Mr. Bailey completed a violence prevention program. He was recommended to do a maintenance program as his pass, and was viewed as qualified by some concerns about his insight and participation.

67In 2018, he completed a mandatory program primer that dealt with managing risk factors.

68In 2020, he participated in the multi-target moderate intensity program for life coping skills. He is wait listed for another program.

69He also completed other periodic programs.

70In 2023, he completed a creative writing course.

71In 2024, he finished the Adrinka-Inspired Rehabilitation Workshop, dealing with culturally relevant methods in resolving conflicts. He also took a course on world religions and indicates that he attends chapel regularly.

Correctional Plan

72In 2018, his correctional plan indicated a willingness to take programs.

73It also indicates that he requires a high need for improvement, finding that he is inclined to commit offences when with associates.

74There is no indication of gang involvement.

Remorse

75Mr. Bailey maintains that he is innocent.

76He says that he is deeply sorry for what happened to the victim and his family, without taking responsibility.

77He has spent time in reflecting on his life and better understands his past mistakes of negative peer association and priority of life choices.

78In institutional reports he generally does not discuss the offence.

Institutions and Timeline

79Mr. Bailey has been incarcerated at various institutions throughout the past 16 years. Below is a brief summary. The events show a pattern of moving from maximum security, periodically downwards to medium security, and then back and forth.

80I pause to recognize that it is not a prerequisite that an offender be in a minimum-security institution to satisfy the threshold to have a jury consider a reduction in parole ineligibility. However, his institutional history is relevant because the records explain that it is associated to risk concerns and misconducts within the institution. R. v. Phillips, 2012 ONCA 54, 288 O.A.C. 351, at para. 8.

81From 2009 to January 2013, he was jailed at Maplehurst and Don Jail. This was while he awaited his trial.

82From January 2013 to June 2015, he was jailed at Millhaven (maximum security). After his conviction based on the outcome of the first trial he was sent to Millhaven Institution, maximum security, for reception into federal custody.

83He stayed at Millhaven Institution until June of 2015, at which time he was transferred to Fenbrook Institution, medium security (now known as Beaver Creek Institution (BCI)).

84From June 2015 to July 2016, he was jailed at Beaver Creek (medium security). He was moved to Beaver Creek after requesting a transfer to be closer to family. BCI supported the request, noting that he was moderate risk. May 14, 2015. (p. 108, Exhibit D):

Concur with the CMT’s recommendation to approve this voluntary transfer application to Beaver Creek Medium-Security Institution. Mr. Bailey has demonstrated so far on this federal term that he does not require the structure and supervision of a maximum security facility. BCI-Med has indicated that they are cautiously supportive and can accommodate his security and programming needs. There is no incompatibility, medical or mental health concerns that would preclude this transfer. He was previously approved for a Medium-security classification. Transfer to BCI-Med is recommended.

85From August 2016 to October 2017, he returned to Maplehurst jail. After the appeal of his first trial was granted, he spent a short period at Central North Correctional Centre in Penetanguishene, Ontario, before being transferred to Maplehurst Correctional Complex in Milton, Ontario. He stayed at Maplehurst Correctional Complex for the duration of his second trial.

86After he was convicted after a second trial, he was again transferred back to federal custody.

87In October 2017, he returned to Millhaven maximum security to serve his sentence.

88In March 2018, he was transferred to Beaver Creek after being classified as a medium-security offender. In February 2018, the Warden at Millhaven wrote that he deserved an exception for the two-year maximum-security designation because of his earlier designation. (Exhibit E Pdf. p. 112):

Mr. Bailey was considered to be fully engaged in his Correctional Plan. Mr. Bailey has demonstrated that he has taken an active role in his Correctional Plan, and that he is aware of its requirements and remains committed to addressing his dynamic risk factors. He successfully completed the Violence Prevention Program (VPP-Moderate Intensity) in 2014, and he was recommended for the VPP Maintenance program. He does not meet the screening criteria for the Multi-Target Stream of ICPM (Moderate Intensity), and he is ready and willing to participate in the ICMP primer and intervention. His accountability and motivation are both assessed as medium signalling that he remains engaged. Although he was involved in three incidents and charges during his approximate year period while housed at BCI Medium, however, none of the incidents resulted in criminal charges or a review for an increase in security level from Medium to Maximum security. There was an assault on staff incident at BCI Medium that was later withdrawn as it was determined through video surveillance that Mr. Bailey had “brushed” the officer’s arm and it was not classified as an assault on staff, although the incident is still listed in RADAR.

I concur with the Penitentiary Placement Board’s assessment of Mr. Bailey’s case. Mr. Bailey has demonstrated that by his overall positive institutional conduct for approximately 1 year, while housed at Medium-security Beaver Creek Institution, and a little over one year in provincial custody, while awaiting trial and MAU, he can be suitably managed at a medium security institution.

89In August 2018, after about five months in medium security, he was transferred to Collins Bay Institution, maximum security following a search where staff found a homemade shank.

90In June 2019, after about nine months in Collins Bay Institution, maximum security, he was transferred to Warkworth Institution, medium security, after again being reclassified as a medium-security inmate.

91In June 2020, about a year later, he was transferred to Collins Bay Institution, medium security.

92In 2022, he was involved in an altercation with a correctional staff member and was transferred to the Collins Bay Institution, maximum security site in November 2022.

93In July 2025, he was transferred to Collins Bay Institution, medium security, based on a finding that he was progressing but still had to be monitored.

Reports about Misconducts

94In summary, Mr. Bailey has been found guilty of incidents of misconduct related to disobedience and crossing boundaries, inappropriate language, and aggressive conduct.

95In provincial custody, he was found guilty of inciting disturbances, assault, insulting staff, and possession of contraband. His behaviour was viewed as unmanageable to the point that he was moved to the Don Jail.

96In general, while in federal custody, there are incidents of assault but not incidents resulting in injury to anyone. He does not have identified addiction issues but has been found to have THC in his system and refused urine analysis on other occasions.

97From August 2012 to February 2015, he collected seven institutional charges. Most were for disregarding or disrespecting authority. He was improving but still needed supervision.

98The Statistical Information on Recidivism (SIR-RI) said he was 33% more likely of committing an offence.

99From June 2015 to August 2016, while at Beaver Creek Institution, he was flagged for three incidents, including drug use.

100From August 2016-October 2017, he was moved from medium security after the Court of Appeal ordered a new trial and he was brought to provincial custody.

101After his retrial and conviction in 2017, while at Millhaven, he got into two incidents of disregarding authority.

102He was moved to medium security and moved to BCI. In 2018, a shank was located in his cell. He was moved to Collins Bay. He was assessed as high risk to harm inmates and staff.

103In August 2019, he was transferred to Warkworth Institution, medium security. He was still noted as high risk.

104He was moved to Collins Bay medium security on an emergency involuntary transfer. He made two improper comments to staff members.

105At Collins Bay from June 2020 to November 2022, his misconduct escalated. He had incidents where he was found guilty of disobeying orders, verbal abuse, throwing a broom, inciting inmates and provoking violence, use of a cellphone, refusing urinalysis, failing a drug test, and smuggling.

106In November 2022, he assaulted a correctional officer.

107From November 2022 to July 2025, he was found guilty of 10 serious charges from refusing to lock up.

108In 2023, he was placed under special management “cage” protocol due to inappropriate comments to female staff.

109From November 2024 to July 2025, the Applicant has been involved in other incidents with improper comments to female staff, using derogatory language.

May 2025 Psychological Risk Assessment Report

110A 13 page, Psychological Risk Assessment (PRA) (May 20, 2025), by Dr. Newman, explains that Mr. Bailey has poor insight and exhibits strong underlying traits of antisocial personality disorder. He has a history of crossing professional boundaries with female staff. He minimizes his misconduct and has insufficient insight into the impact of his conduct on others. He is at a high range of risk to violently re-offend. It states that the most relevant risk enhancing historical factors are a history of violent/anti-social attitudes and behaviour, problems in both intimate and non-intimate relationships, failure to abide by conditions of release.

111I have considered the PRA report of May 2025 carefully given its findings that he is high risk. The assessment is clearly against the Applicant’s position that he has made sufficient progress and changed. It finds that he is at a substantial risk to re-offend putting him a category consistent with 45% risk of violent re-offending within 5 years.

112Although the Applicant declined to make further submissions after submitting this important report in my review of the PRA, I have some concerns about aspects of the reliability of the report for the following reasons.

113First, it relies heavily on the summary of information from a five-year-old correctional plan from July 13, 2020 (see p. 7 of the PRA). The psychologist states that he asked for an update from the parole officer and was told that with the exception of a 2021 Motivation Support Module, the Applicant’s behaviour remained “relatively unchanged’ and therefore the rating across dynamic factors remain accurate. Clearly an updated plan would have been beneficial to better understand his current circumstances.

114Second, the PRA indicates that there has been no prior psychological risk assessment on the Applicant’s file. This further raises the concern that this PRA, required more up to date and better tracking of information. Five years while incarcerated is a long time without an update about his correctional plan.

115The psychologist interviewed the Applicant for 2 hours online (interrupted by a technical breakdown) to get additional information. However, the report leans heavily on the 2020 information.

116Third, the PRA author did not conduct a personality assessment inventory to understand the Applicant’s personality structure. The author then proceeded to assess the “current risk” based on what appears to be influenced by a dated set of materials. (See p. 9) Further, there is conflicting information not reconciled adequately with up-to-date information. For example, the information indicates that the Applicant has excellent program performance reports regarding employment, no substance use issues, completed his high school education, and not been diagnosed with any major disorder, while reporting anxiety.

117That said, this report’s findings were not contested or explained by the Applicant. The court afforded the Applicant an opportunity to respond, and the Applicant chose to make no further submissions about the report and not to provide supplementary information to address its findings, provide a counter perspective or clarify information.

118Despite my concerns noted above, I must consider the report’s findings. The assessment finds him being “high need” and “high risk”. I find the PRA is relevant to the evaluation of the legal screening test, but not dispositive. It is only part of the total information presented by the Applicant that I must consider. I give the report limited weight, but I accept its more general findings that the Applicant has areas that require improvement and that he is a significant risk to public safety until they are addressed and consistent progress is established.

119I pause here to explain that this May 2025 PRA was not submitted in the Applicant’s initial record of August 2025, or supplementary application record in April 2025. During my review of the about 400 pages of the combined application record, I observed that a parole officer’s report’s referred to this assessment. As a result, on March 13, 2026, the court directed applicant’s counsel by email to advise whether this report would be submitted. This was in addition to the direction organizing the extensive application record appropriately.

120The Court then had to follow-up with Applicant’s counsel for a copy of the report on May 6, 2026, because it had not been provided. When it was eventually submitted, it was incomplete, missing a crucial page. A full report was ultimately provided in early June.

121In relation to this PRA, the Applicant’s counsel did not file further submissions. The Crown provided supplementary submissions on June 8 relying on the report to advance its position that the Application should not proceed before a jury.

122At a case management appearance on June 26, the Applicant’s counsel indicated they took no position on the Crown’s June 8 written submissions. Counsel also sent an email stating the same on June 22 to the court. Since this is a written application, the Applicant’s counsel was instructed on June 26 to put this into a written submission as part of the record, due July 3. They did not meet that deadline and sought an extension by emailing the court on July 16. I have discussed this background and my concerns in a separate endorsement concerning the extension request. Eventually, on July 24, Applicant’s counsel wrote a brief letter stating: the defence will not be making further submissions on this matter.

Risk of Re-offending

123The Applicant’s SIR score +3 places him in a group of 2 out of 3 offenders with similar scores who will not commit an indictable offence after release.

124In 2015, a risk assessment says he is in the low-moderate range of risk, and risk of violent recidivism is low-moderate. The 2025 PRA puts him in a higher risk range.

125He has had escorted temporary absences to attend medical appointments since 2020 without incident.

Health Issues

126Mr. Bailey suffers from chronic renal (kidney) failure, valvular disease, and other health issues. His treatment is to manage them by limiting stress. This is difficult with the tension in the tense and violent jail context.

127He has experienced some physical health issues of a nerve injury in his hand, joint conditions, tendon and ligament disorders, and suffers from migraines.

128He also struggles with mental health issues of anxiety and poor self-esteem but seeks support through institutions mental health services. He is not taking medication but has in the past as needed to help him cope in an environment that can feel hopeless.

POSITIONS

129The Applicant submits that based on his character; rehabilitative efforts, community support, and ongoing health issues, there is a reasonable prospect that a jury would reduce or end his parole ineligibility. At the time of the offence, he was young, with a limited criminal record. He has worked within jail to be a positive person focused on rehabilitation. He has worked and improved his education. He has taken rehabilitation programs to address risk. He has strong community support to foster reintegration.

130The mental health issues have exasperated the harshness of his sentence and have made time spent in custody more onerous. The 25-year parole ineligibility is no longer proportionate.

131The Crown Respondent submits that the Applicant committed a brutal murder with confinement of both the deceased and his mother on November 12, 2009. He had a recent criminal record at the time for crimes of violence. Since then, he has not shown remorse, insight, nor empathy. His institutional record reflects anti-social behaviour. He has not improved. He has become worse in important ways. This includes his mistreatment of woman.

132In his latest correctional report, he is viewed as a high risk to the public. He is a continuing danger to society and has not changed.

133In the Crown’s June 8th submissions, the Crown highlighted the May 2025 PRA’s contents under the heading of current assessment of risk puts Mr. Bailey at substantial risk to re-offend violently.

ANALYSIS

134The fundamental question is whether there is sufficient evidence that there is a reasonable prospect that the application would succeed. This means a jury would accept that the Applicant has changed and rehabilitated to justify a reduction in parole ineligibility. In substance, the focus is whether there is proof of progress in terms of long-term growth demonstrated by positive conduct and reduced risk to the public and victims’ safety.

135This requires a totality assessment of the factors, with a recognition that this is a highly individualized assessment.

136I will review the factors in totality (while discussing those that support and detract from the application being granted) to determine if the screening test is met on a balance of probabilities. R. v. Dell, 2018 ONCA 674, [2018] O.J. No. 4094 (C.A.) at para.81. For some relevant considerations, this assessment is complex and variable. There will be some factors that pull in both directions, in that they can be in part contrary to the application being granted, and in other part supportive, and to differing degrees.

137The total circumstances of the murder are horrific.

138Mr. Bailey acted (with others) to forcibly confine and shoot the victim to death. The mother was also a direct victim, forcibly confined and then had to attend to her dying son in the aftermath. I use the word direct here, because I appreciate the family of the victims are also deeply impacted.

139The robbery was planned. The forcible confinement of the victims and the execution style murder is on the severe end of the spectrum of murders. The robbers then stole his vehicle and fled.

140Mr. Bailey committed the murder while previously found guilty of violent offences and bound by court orders not to possess a weapon and to abide by probationary terms.

141I have considered the updated victim impact statements. The impact on the victims is a very important factor. I also understand that this has been a prolonged process adding to their anguish. This family has been through two trials and two appeals over several years, that has added to their trauma.

142Their written statements make visible the devastating long-term consequences of these crimes. They help to understand how damaging these crimes continue to be on their lives. The crimes have devastated the family, and for which they continue to suffer trauma. This information reflects the gravity of the harm and provides a better appreciation of the true nature of the offences.

143I recognize that the victims’ family should not be subjected to a third court proceeding unnecessarily, even if it serves a distinct legal purpose from a trial and one that is an important part of our justice system.

144With respect to remorse and insight, Mr. Bailey does not accept the jury's verdict. He does not have remorse for the crimes. He states that he feels sorry for what happened to the victims but does not take accountability.

145Remorse, when genuinely expressed and more importantly communicated through rehabilitative steps and efforts dedicated to acquiring insight, is a relevant factor and can be important.

146While an acceptance of responsibility and genuine remorse indicates insight into the offending conduct, maintaining one’s innocence or a related lack of communicated remorse is not determinative. In some cases, where the other factors support granting the application, this issue can be left to the jury to determine to consider. See R. v. Shaftler; Morrison at para. 82; Al-Shammari at para. 67; R. v. Figueroa, 2024 ONSC 4173 .

147In this context, the Applicant’s conduct while incarcerated is a significant measure of whether they have acquired insight into their risk factors.

148Due to misconducts and his associated risk level, he has not been able to remain in lower security rating. That said, he has also spent sustained periods in medium security.

149His institutional discipline record reflects numerous infractions of disobedience, disruption, minor physical incidents with guards, and abusive language. The totality of misconducts shows a disrespect for jail staff. On the other hand, he appears to work well at jobs and with persons that support his rehabilitation.

150Mr. Bailey has a criminal record, albeit limited, for violence preceding the murder. He was relatively young.

151His May 2025 PRA report finds that he is in the range of high risk to violently reoffend. Despite my concerns about parts of the report as explained above and the reduced weight I attach to it ultimately, the PRA’s findings are consistent with his institutional misconduct, inconsistent progress, and that he has not made sustained improvement in important areas relevant to public safety.

152This information must be viewed in the context. He was 21 years old at the time of the offence. He is now 37 years old.

153At the time of the offence, he was a young man with a supportive family and a limited prior criminal record.

154Mr. Bailey has not become involved with gangs or identified to have any drug addiction issues. That does not mean he has not used marijuana or similar drugs. He had a positive THC analysis in July 2018 and December 2022. He refused urine analysis in 2023 and 2024.

155He has avoided negative peer groups which influenced the offence for a prolonged period in a difficult confined setting.

156His institutional discipline record must be understood in the full context of 16 years of incarceration. They involve some incidents that are viewed as violent and aggressive. That said, when considered in totality, over the 16 years, he has also been consistently non-violent.

157While I recognize the troubling incidents that are significant negative factors such as possessing a shank and on multiple occasions showing a lack of respect towards female guards, he is also described over the years by many staff in education, employment, parole, and daily interactions as usually polite and respectful. This demonstrates the need for more information about these incidents. While relevant factors, I do not accept that that the negative incidents alone automatically define his institutional conduct.

158When he first started to serve his sentence and entered maximum-security jail, he was categorized as requiring supervision and a high risk based on the violent offence but clinically assessed as a low-to-moderate risk of recidivism, including for violence.

159By 2015 and when he was 26 years old, he was found to be suitable for medium security. After he passed the violence prevention program, noted to be a cautious pass, he was recommended to participate in the violence prevention maintenance program. There was an emphasis on problem-solving in relation to future financial problems. This may be indicative of a correlation to the offence. Concerns about impulsivity, family violence, and anger management were identified as areas of concern within that designation.

160In March 2018, at the age of 29 to 30 years old, after being found guilty at the re-trial, it was recommended that he be placed in medium security. He had earlier already spent a year at BCI without issue.

161Up to this point, there were no findings of violent misconducts.

162The 2018 correctional plan notes medium motivation for change.

163In 2019, at 31 years old he was recommended to move to Warkworth medium-security facility. This was after being found with a shank at BCI and moved involuntarily to Collins Bay maximum security. He did not use the weapon and had it for protection. He had no issues at Collins Bay. In this report, he is noted to be high risk and need offender management and to have been aggressive with staff. Yet, he is also noted as acting appropriately with staff and recommended for medium security. The report indicates that he has not been involved in any violent incidents since incarceration from 2012.

164In a 2020 report for multi-target intensity program, he is found to have made some progress, moving from the status of “needs a lot of improvement” to needs “some improvement” in numerous areas regarding conflict and interpersonal relationships, while the ultimate conclusion is that he needs a lot of improvement to manage risk.

165In November 2022, he was recommended to return to maximum security for being verbally and physically aggressive with a guard and having other incidents of disobedience. The incident involved a guard intervening when music was played from his cell while he cleaned. The situation escalated verbally and physically with disrespectful language. No one was hurt. He apologized and explained that he was experiencing stress from the passing of his mother and other personal circumstances. The report noted he had 20 incidents in total, including various acts of disobedience, disrespectful language, and unauthorized possession of a cellphone, and that the transfer was warranted.

166In November 2023, he was placed on restriction of being in a cage, while being interviewed by female staff. This was removed in 2024.

167In July 2025, unit managers supported his transfer to medium security at Collins Bay, while the report summarized several incidents of disobedience and improper language use towards staff. He is noted to be high risk to public safety.

168His cumulative reports indicate that he has consistently been willing to participate in programs when available.

169He has taken rehabilitation programs and done relatively well. This includes violence prevention, managing risk, and better choices.

170Regarding his education, he has completed his OSSD. He struggled in school before the offences, in part because of mixture of comprehension and language issues. He worked to overcome those issues. His teacher, Mr. Gray, spoke of him as always polite and respectful.

171He has a good work history. He has been steadily employed in service, cleaning, and cooking. He worked as a range representative at Millhaven, which indicates real growth.

172He has taken up spiritual or religious practices including yoga, meditation, and attending chapel while practising his own faith.

173He has the support of his family. The family and friends he has remained in contact with over the years attest to his transformation while in custody and express their love and support for him.

174He has distinct health issues that are impacted by the stress of incarceration and its conditions which are relevant factors at this screening stage.

Other factors

175Section 745.61(2) requires the screening judge to consider “any other matters that the judge considers relevant in the circumstances”. The Applicant’s submissions or materials did not delve much into his social history and context while serving his sentence. In my view, this is a relevant consideration to understand his records, risk assessments, health and overall position, even on a limited record on this point.

176Mr. Bailey is a Black man who has served 16 years in jail, moving from a young adult to a grown adult with physical and mental health challenges while exhibiting some rehabilitation progress.

177The law firmly recognizes that Black people experience jail distinctly and more harshly than others due to systemic factors. In Dorsey v. Canada (Attorney General), 2025 SCC 38 at para. 72 the Supreme Court recognized that when it comes to security classification, “over-classification disproportionately places Black and Indigenous inmates in higher, more restrictive security facilities with a lesser degree of access to rehabilitative opportunities that promote successful reintegration into the community upon release. Notably, the inability to reach a lower security classification can preclude inmates from qualifying for culturally responsive environments and programming.”; see also Hills at para. 105. Canada, Office of the Correctional Investigator (OCI).

178Despite being rated as a population having a lower risk to re-offend and lower need overall, Black inmates are more likely to be placed in maximum-security institutions. Since 2013, the OCI reported that Black prisoners were 1.5 times more likely to be placed in maximum-security institutions where programming, employment, training, education upgrading, rehabilitative programming, and social activities are limited. Furthermore, Black persons experience discrimination by correctional officials through the use of racist language, as well as being ignored and disregarded in ways that increase feelings of marginalization, exclusion, and isolation. A Case Study of Diversity in Corrections: The Black Inmate Experience in Federal Penitentiaries. Ottawa, 2013.

179Black persons were consistently overrepresented for discretionary charges such as disobeying an order or a rule, disrespect toward a person or staff member, and jeopardizing the safety of the institution. Conversely, Black prisoners were underrepresented in categories of charges requiring less discretion and more concrete evidence, such as damaging or destroying property, possession of an unauthorized item, and failing a urine test. See also Office of the Correctional Investigator Annual Report 2021-2022, Update on the Experience of Black Persons in Canadian Federal Penitentiaries at pp. 52-53, 58-60.

180Consistent with these studies, in a report by his parole officer of July 2025, Mr. Bailey said that he has experienced discrimination in jail.¹ The report says that he feels more discrimination while in jail rather than he did while in the community but did not provide specific examples. In my view, this should have been further explained.

181The nature of the infractions that are cited as exemplary of his risk are consistent with the disproportionate impact of discretionary charges on Black people that is well documented.

182It is concerning that on this record, this 2025 parole officer’s brief comment, is the only institutional report over 16 years that appears to have canvassed Mr. Bailey’s experience with mistreatment, despite it being a serious systemic issue in the federal jail system documented by the OCI since 2013. More information about this context is important.

183Factoring the OCI reports and recognition by the Supreme Court of this systemic problem, a relevant contextual factor is how a Black person that entered jail at the age of 21, may experience the federal jail system over a prolonged period. This is material information that should be included by the institution (and Applicant where possible).

184This relevant factor is amongst others including that Mr. Bailey has deteriorating health. Particularly harsh or exceptional custodial effects warrant consideration of their impact on the offender. R. v. Oryia, 2026 ONCA 166 at paras. 21-22. This must necessarily include their experience with discrimination that pertains to overall treatment, access to health care, rehabilitative programs or treatment, and security classification.

CONCLUSION

185A contextual analysis of the total materials demonstrate that Mr. Bailey poses a serious risk to violently reoffend.

186Mr. Bailey has made some notable progress, but it is ultimately limited and inconsistent on this record. I hope that he will further dedicate himself to rehabilitation and consistent growth. His health challenges present distinct challenges for coping and therapy in the jail context but he is receiving some treatment. The combined information does not satisfy the requisite legal standard.

187Overall, I find that after considering the total record, it has not been established that there is a reasonable prospect that this application would succeed.

188The application is dismissed.

189I make no finding on when a further application may be brought, pursuant to s. 745.61(4) since it was not argued by the parties in their materials.

190If there is a future application, I recommend that the areas of concern explained in this decision be addressed and that the Applicant consider obtaining a Morris (or Enhanced Post-Sentence Report) to more fully explain his full institutional experience and insight to assist the court.

Mirza, J.

Released: July 27, 2026

CITATION: R v. Bailey, 2026 ONSC 4363

Footnotes

1. 1Applicant's supplemental application record at p. C-1-525; or Crown's responding materials at p. B167