ONTARIO COURT OF JUSTICE
BETWEEN:
HIS MAJESTY THE KING
— AND —
LENNIE MIDDLETON
Before Justice André Chamberlain
Heard on September 19, October 8, 2025
Disposition Entered on November 28, 2025
Written Reasons for Sentence released March 11, 2026
Karolina Visic counsel for the Crown
Alison Craig counsel for the accused Lennie Middleton
1Lennie Middleton is subject to a 10-year long-term supervision order (LTSO) imposed by Justice Kelly in the Superior Court of Justice on February 19, 2014. He has pleaded guilty to breaching that order by violating a boundary condition. The question I must answer is how the sentencing range applies to breaches of a long-term supervision order, considering Mr. Middleton’s history of breaches, some prosecuted, and many dealt with under the supervisor’s authority, his serious criminal record, weighed against the nature of the breach and the application of the Gladue principles.
The Agreed Statement of Facts
2On February 19, 2014, Lennie Middleton was convicted of assault with a weapon and sentenced to two years, time served, and to a 10-year long-term supervision order. On August 23, 2024, following a recent suspension for drug use, Mr. Middleton reviewed the conditions of his LTSO with his supervisor. Mr. Middleton’s LTSO conditions included a geographical restriction, not to be within the boundaries of Lakeshore Boulevard to the south or Bloor Street to the north, the Don Valley Parkway to the east, and University Avenue to the west, except while travelling to and from all court appearances and while travelling to or while attending any scheduled work.
3As of August 2024, Mr. Middleton was a resident of the Keele Community Correctional Centre (Keele CCC). He was staying there during the week and had been granted a travel permit to reside with his partner, Vicki Humphrey, in Scarborough from Friday night to Monday morning. Mr. Middleton was subject to a curfew from 11:00 p.m. to 6:00 a.m. during these visits.
4Mr. Middleton started working as a landscaper at Pagoda Gardening Limited in 2020. The company is located in Scarborough. Mr. Paquin, who operated Pagoda Gardening Ltd., often employs men who reside at the Keele CCC. He recognizes the importance of monitoring his employees’ movements and is aware that someone might use work as cover for other activities. As a result, he maintains good relationships with parole officers, other officials, and supervisors at the Keele CCC.
5Mr. Middleton was found on Coatsworth Street, a lane south of Dundas Street and east of Parliament Street in Toronto, just before 1:00 a.m. in the early morning of August 26, 2024. Police officers on patrol in the area at the time observed a silver 2007 Chrysler driving on Parliament Street without its lights on. The vehicle was registered to Vicki Humphrey, Mr. Middleton’s girlfriend. Vicki Humphrey’s residence is approximately 30 km from the location where Mr. Middleton was found.
6Officers investigated the vehicle and its passengers, Mr. Middleton and his female passenger, Stacy Arseneault. Mr. Middleton repeatedly stated that he was on his way to work and was permitted to be outside curfew hours for work-related reasons, mentioning that he was running late. It was evident that Ms. Arseneault was under the influence of some substance. She fell asleep in the passenger seat while the police interacted with and arrested Mr. Middleton. During the arrest, as the police tried to wake her to leave, they struggled to do so.
7Mr. Paquin confirmed to the police that Mr. Middleton was scheduled to start work at 7:00 a.m. on Monday, August 26, 2024, and not any earlier. He said that in August, there’s no reason for a landscaper to work at 1:00 a.m. Further, he indicated that Mr. Middleton has never shown up six hours early for a shift.
8Mr. Middleton did not produce his driver’s license and insurance. He called his girlfriend, Ms. Humphrey, to ask where their required paperwork was. Since Mr. Middleton was out past 11:00 p.m., he was breaching both his curfew and boundary conditions. He also failed to provide his release certificate or his Correctional Service of Canada (CSC) identity card. Ms. Humphrey arrived later with some documents, which were shown to the police.
9Mr. Middleton became upset when he was arrested. An unnamed gentleman who identified himself as a friend of Mr. Middleton and clearly knew him personally came to assist. The friend noted that it was evident from Mr. Middleton’s demeanour that he had had a “slip.” He tried to talk to Mr. Middleton, telling him to relax and that everyone has a “slip.”
Further Evidence
10I also benefited from the testimony of his long-time parole supervisor, Ms. Vonetta McGhie. Ms. McGhie testified that she has been Mr. Middleton’s parole officer since 2016 and his direct supervisor from 2020 until June 2024. Her office was located in his residential building for much of that time, which led to frequent contact. She described the supervision regime as intensive, including urinalysis, offering mental health supports, addictions counselling, and Indigenous programming.
11Ms. McGhie identified substance use as Mr. Middleton’s main difficulty. She observed that when he is not using or is sober, he appears as a “completely different person.” She noted that under the influence, his risk of offending increases. She testified that several of his early suspensions were connected to substance use and environmental triggers like being around other drug users. Ms. McGhie also mentioned that although Mr. Middleton occasionally reported concerns about relapse, she stated that he sometimes withheld enough information to enable harm reduction steps.
12On the more positive side, Vonetta McGhie also noted that Lennie Middleton’s performance improved significantly after engaging in Indigenous-specific programming and addiction treatment. This was demonstrated by his suspensions becoming more spaced out. He reliably complied with curfews, participated in programming, and showed respect to staff. She also noted that his functioning improved when he started employment and participated in programs at the Centre for Addiction and Mental Health (CAMH). He repeatedly volunteered to redo the same program cycles, which she viewed as an indicator of his commitment to recovery.
13Ms. McGhie acknowledged that there was consistent and notable improvement during the supervision period. In cross-examination, she confirmed that he showed commitment, progress, and positive involvement with programming.
14Ms. McGhie confirmed that Mr. Middleton had a total of 14 suspensions of his LTSO. This case marks the fourth criminal charge for a breach of his LTSO. Not all suspensions resulted from new criminal behaviour; many were administrative or substance related. Vonetta McGhie testified that his LTSO expires in 2026 and that, due to his ongoing challenges, continued therapy and addiction supports will be crucial. She expects to recommend a Section 810 Order due to the ongoing risk. She also believes that Mr. Middleton may benefit from Indigenous-specific programs, although he has completed similar programs in the community multiple times.
15Mr. Middleton testified about his experience in custody since August 26, 2024. He was almost constantly triple-bunked, often sleeping on the floor. Cells were occasionally affected by toilet overflows containing human waste. He described long lockdowns, including one lasting 120 hours, with no access to showers or fresh air. He reported limited access to clothing, visits, programming, and meaningful out-of-cell time due to ongoing staff shortages. During cross-examination, he stated that all lockdowns resulted in total confinement to cells and that he had no access to programs during those times.
The Position of the Parties
16The Crown requests a sentence of four years’ imprisonment, less pre-sentence custody, describing this as a serious breach within the upper-mid range of LTSO sentencing jurisprudence. They highlight the now four convictions for LTSO breaches, totalling 14 breaches, along with 95 adult and youth convictions. He was with a vulnerable woman who was clearly under the influence at the time, and the boundary breach coincides with the area where most of his prior serious offences occurred, including offences involving vulnerable women. They also point out that he was deceptive with the police about working and the circumstances surrounding his arrest. The Crown argues that these factors place his conduct in the middle range of seriousness, despite no new offence being committed.
17The Crown also argues that there is insufficient evidence that systemic or background factors related to his Indigenous background lessen moral blameworthiness for this breach, which it describes as a conscious choice. They propose that Gladue should be taken into account, but its influence on culpability is limited because it does not substantially alter his choices that night, and therefore, his sentence should not be substantially reduced due to his background.
18The defence describes this breach as minor, non-violent, and consistent with occasional lapses expected during long-term community supervision. They argue that the roughly 14 months already served are sufficient and that further institutionalization could hinder rehabilitation.
Lennie Middleton’s Background
19The defence presented evidence, including references within the correctional plan and counselling materials, describing Mr. Middleton’s early life marked by significant trauma, such as childhood exposure to physical, emotional, and sexual abuse; time spent in shelters and training schools; disconnection from a stable and supportive family environment; and the intergenerational impacts of colonization manifesting in chronic instability, substance dependency, and disrupted cultural identity.
20Counsel argued that these experiences are directly relevant to his long-term struggles with substance use and institutionalization, and have influenced cycles of relapse and rehabilitation throughout the supervision order.
21Mr. Middleton’s Indigenous identity seems to have been meaningfully engaged during his supervision period, especially as he started taking part in Indigenous-specific community programs and cultural supports. Ms. McGhie indicated that Indigenous programming, along with addictions treatment at CAMH, “did wonders for him,” promoting stability, better functioning, and fewer suspensions. She also observed that after he turned toward Indigenous programming, his behaviour improved and the time between suspensions grew longer.
The Aggravating and Mitigating Circumstances
22The Criminal Code of Canada, at section 718.2, states:
A court that imposes a sentence shall also take into consideration the following principles:
(a) a sentence should be increased or reduced to account for any relevant aggravating or mitigating circumstances relating to the offence or the offender
23The aggravating and mitigating factors include elements of Lennie Middleton’s background, such as the unique systemic or background factors related to his Indigenous identity. I must also take into account the nature of his crimes, the timing of his guilty plea, and any other evidence presented at this sentencing hearing. This also involves considering legal guidance from the Criminal Code and directives from higher courts regarding particular aspects of this case. Some of the aggravating circumstances are:
(1) This is now Lennie Middleton’s fourth LTSO breach conviction.
(2) He has had a total of 14 breaches, the majority of which were dealt with within the CSC’s jurisdiction.
(3) Mr. Middleton has a criminal record with 95 youth and adult convictions.
(4) This criminal record involves having subjected vulnerable women to violence. At the time of his arrest, he was with a vulnerable woman who was clearly intoxicated, although there is no suggestion that he was violating or abusing her in any way.
(5) He was breaching a legally set boundary in an area where he has frequently faced legal issues, as well as people and situations that could trigger his own drug use.
(6) Though there was no definitive proof of drug use that night, though I accept that based on his actions and demeanour, he had clearly relapsed in the hours before his arrest.
(7) Mr. Middleton’s feeble attempts to deceive the police by claiming he was heading to work at 1:00 a.m., driving to a landscaping job with a woman who was clearly intoxicated, are rather pathetic though, strictly speaking, aggravating.
24The following are mitigating factors:
(1) He entered a guilty plea, saving the Crown and courts valuable resources and time.
(2) His plea and personal statement express regret and remorse for his actions and show a commitment to continue his recovery.
(3) He has had a positive work history and an ongoing employment opportunity. He began working with a landscaping company in 2020, and, despite his struggles, has benefited from continued support from this employer, who remains willing to work with Mr. Middleton and others similarly situated to help them gain valuable work experience.
(4) He has benefited from the long-term and unwavering support of his spouse, Vicki Humphrey.
(5) His tragic background and the systemic factors as part of the Gladue analysis is a significant mitigating factor.
(6) Lennie Middleton has, in my view, made significant progress in his rehabilitation. He has participated when directed by his supervisor and has often sought out programs, some repeatedly, demonstrating a commitment to recovery.
(7) Despite the recurrent and ongoing breaches of the terms and conditions of his LTSO, it is noteworthy that there have been no incidents of violent offending since 2014.
Legal Analysis
25The facts and background surrounding this case are not in question. What is at issue is how these facts, and the aggravating and mitigating circumstances of this case and of Lennie Middleton, lead to the appropriate sentence.
26The Crown is justified in highlighting the significant criminal record, past propensity for violence, and his history of 14 breaches since he has been on the LTSO, with this fourth breach resulting in a conviction. I also accept the Crown’s proposed range as outlined by my colleague, Justice Greene, in her judgment regarding Lennie Middleton, at paragraph 37, where she states:
37 With these aggravating and mitigating factors in mind, it is helpful to consider the range of sentences normally imposed for breaches of Long Term Sentence Orders. The range seems to be between nine months and five years. Where there is a single breach with prior compliance then sentences in the one year mark are imposed. Where there are multiple breaches or the breach is considered serious sentences as high as five years are imposed.
R. v. Middleton [2019] O.J. No. 2250 | 2019 ONCJ 280
27However, I disagree with the Crown’s contention that somehow the Gladue considerations are minimized because, in essence, there is a lack of a nexus between the offence committed and Lennie Middleton’s Indigenous background and the associated impact on his life and circumstances.
28The Ontario Court of Appeal, in R. v. Kreko, citing R. v. Ipeelee, addressed the issue head-on, including the impact of systemic and background factors on sentencing for Indigenous offenders and the need for those factors to be connected to the commission of the offence.
[21] The jurisprudence makes it clear that no causal link is required. In R. v. Ipeelee, [2012] 1 S.C.R. 433, [2012] S.C.J. No. 13, 2012 SCC 13, the Supreme Court held that it was an error to [page691] require an aboriginal offender to establish a causal link between his or her background factors and the commission of the offence(s) in question before he or she is entitled to have those factors considered by the sentencing judge. The court suggested, at para. 82, that requiring a causal connection demonstrated "an inadequate understanding of the devastating intergenerational effects of the collective experiences of Aboriginal peoples", and also imposed an evidentiary burden on the offender that was not intended by Gladue.
[22] The court continued, at para. 83:
[I]t would be extremely difficult for an Aboriginal offender to ever establish a direct causal link between his circumstances and his offending. The interconnections are simply too complex. The Aboriginal Justice Inquiry of Manitoba describes the issue, at p. 86:
Cultural oppression, social inequality, the loss of self-government and systemic discrimination, which are the legacy of the Canadian government's treatment of Aboriginal people, are intertwined and interdependent factors, and in very few cases is it possible to draw a simple and direct correlation between any one of them and the events which lead an individual Aboriginal person to commit a crime or to become incarcerated.
Furthermore, the operation of s. 718.2(e) does not logically require such a connection. Systemic and background factors do not operate as an excuse or justification for the criminal conduct. Rather, they provide the necessary context to enable a judge to determine an appropriate sentence.
[23] The court explained that what is required is that the factors must be tied to the particular offender and offence(s) in that they must bear on his or her culpability or indicate which types of sanctions may be appropriate in order to effectively achieve the objectives of sentencing. Finally, the court in Ipeelee also made it clear that s. 718.2(e) applies to serious offences: see paras. 84-86.
R. v. Kreko, 2016 ONCA 367,
29In other words, Lennie Middleton’s background as an Indigenous person and the effects of colonial practices in this country are not supposed to explain or be directly connected to the actions that brought him before the Court, but the information derived from his systemic factors and traumatic life experiences should be analyzed as part of assessing his moral culpability to determine an appropriate sentence.
30The following systemic and individual factors were also referenced as part of the Gladue analysis: a history of institutional abuse and displacement from family supports; the impact of colonial legacies, including the over-representation of Indigenous persons in custody and child welfare systems; substance addiction as a chronic, trauma-linked condition with his use beginning at a very young age; the role of poverty, unstable housing environments, and limited community anchors earlier in adulthood; repeated institutionalization since youth, shaping coping mechanisms and criminogenic pressures.
31I have also considered the very tragic background of a person who was placed in care at the age of 9, and in a twist of cruel irony that shows the failure of our colonial approach to troubled children when the state removes them from their family and culture, it then turns around and places them in situations where they face abuse and horrors beyond imagination. It is a serious stain on our society that we turned a blind eye to the physical, emotional and sexual abuse of children under our care, whether in foster care or training school, or even under the supervision of their own families by protective authorities.
32It is no wonder that from a very young age, Lennie Middleton turned to substance use and antisocial behaviour as a means of coping with his trauma.
33When applying section 718.2(e), we are instructed to adopt a remedial approach to sentencing, especially concerning Indigenous people. The Supreme Court has repeatedly found that the criminal justice system discriminates against Indigenous individuals and fails to deliver meaningful justice to victims, those accused, or those who have caused harm: see R. v. Williams, 1998 782 (SCC), [1998] 1 SCR 1128, at para 28, Gladue at para 65, Ipeelee at paras 59-67, Barton at para 199, R. v. Sharma, 2022 SCC 39 at para. 114, Ewert v. Canada, 2018 SCC 30, [2018] 2 SCR 165, at para. 57.
34I am also reminded that the Supreme Court indicated in R. v. Gladue, 1999 679 (SCC) at paragraph 68 stated:
. . .Moreover, as has been emphasized repeatedly in studies and commission reports, aboriginal offenders are, as a result of these unique systemic and background factors, more adversely affected by incarceration and less likely to be “rehabilitated” thereby, because the internment milieu is often culturally inappropriate and regrettably discrimination towards them is so often rampant in penal institutions.
35In R. v. Ipeelee, which specifically involved breaches of LTSOs, the Court reaffirmed that Gladue applies fully in the LTSO context. Judges must (a) consider offender-specific systemic and background factors, and (b) examine sanctions and procedures appropriate to Indigenous identity, while still respecting the public protection purposes of Part XXIV. Ipeelee also instructs sentencing courts to acknowledge the ongoing effects of colonialism, displacement, and residential schools, and to ensure the analysis goes beyond merely listing background facts without considering their impact on the appropriate sentence.
36Defence counsel argued that the very struggles that lead to occasional lapses, such as susceptibility to high-risk environments, stress, and residual trauma, are themselves manifestations of Gladue-related impacts. They maintained that the breach was, in the full context of a decade of supervision, a “minor” breach, and that Ipeelee warns against relying solely on deterrence, which can undermine successful long-term reintegration.
37So, the question today is whether further incarceration is necessary to address the fourth breach of his LTSO. It cannot simply be that the number of breaches, despite the aggravating circumstances, alone warrants additional jail time.
38This breach should be considered within the context of Lennie Middleton's lifetime of struggles and his pattern of making poor choices that have hurt others. But I also need to look at it alongside his more recent challenges. Yes, he still battles addiction and has relapsed at times. But it is also true that there have been no incidents of violence since 2014. In some ways, he is being managed through the LTSO.
39Furthermore, it cannot be overstated that Lennie Middleton has, in my view, made significant progress in his rehabilitation. Has it been perfect? No, it rarely is. But considering his background, his very tragic childhood traumas, his early exposure to drugs as a pre-teen, and his long-term involvement in the criminal justice system, along with a diagnosis of antisocial personality disorder, all culminating in a designation as a dangerous offender and a 10-year LTSO, it is remarkable that he has made so many efforts toward recovery. He has repeatedly participated in programs and has shown determination and commitment to making positive changes in his life.
40However, he is not yet finished, and although his efforts and commitment have improved considerably over the past few years, he still has progress to make.
41I am satisfied that the time in custody, calculated at 460 days, can be credited as 690 days, given the significantly difficult conditions he has endured. I have written repeatedly about the negative impact of staff shortages, leading to extended lockdowns, triple-bunking, and unsafe, unsanitary conditions. It is a stain on our provincial institutions that they provide individuals they have a duty to care for and house with such inhumane and substandard conditions.
42Mr. Middleton acknowledged he was making “selfish decisions” and causing others pain. But he also expressed a desire to change, to be sober, stable, and to continue seeking community support. He deserves that chance, and his progress and commitment to recovery, as demonstrated through his repeated participation in programs and increased engagement since engaging in Indigenous programming, specifically through CAMH, must be recognized as a means of addressing what may keep him out of trouble in the future.
43As part of that support for his rehabilitation, I will suspend the passing of sentence, and Lennie Middleton will be placed on probation for a period of two years.
Written Reasons Released: March 11, 2026
Signed: Justice André Chamberlain