Reasons for Sentence

File No.: CR-24-10000110-0000
Date: 2025-02-28
Ontario Superior Court of Justice

Between:
His Majesty the King
and
Jordan James O’Brien-Tobin

K. Simone and A. Nash, for the Crown
R. Cutruzzola and J. Berman, for Jordan O’Brien-Tobin

Heard: February 6, 2025
Kelly J.

Introduction

[1] Mr. Jordan James O’Brien-Tobin has pleaded guilty and been convicted of second degree murder. Mr. O’Brien-Tobin stabbed 16-year-old Mr. Gabriel Magalhaes in the chest as he was waiting for a TTC train to take him home. Mr. O’Brien-Tobin and Mr. Magalhaes were strangers to each other. Tragically, Mr. Magalhaes died within an hour of the stabbing.

[2] Mr. O’Brien-Tobin appears before me now for sentencing.

[3] The imposition of a life sentence without eligibility for parole until Mr. O’Brien-Tobin has served at least 10 years of his sentence is mandatory following a conviction for second degree murder. However, the sentencing judge may increase the period of parole ineligibility from 10 years up to a maximum of 25 years.

[4] Crown counsel seeks a period of parole ineligibility of 18 years. Counsel for Mr. O’Brien-Tobin submits that the appropriate period of parole ineligibility is 12 years. They agree on the ancillary orders to be imposed: DNA, a weapons prohibition and a non-communication order.

[5] For the reasons set out below, Mr. O’Brien-Tobin will not be eligible for parole until he has served 18 years in prison.

The Principles Governing the Parole Ineligibility Determination

[6] Pursuant to ss. 235(1) and 745(c) of the Criminal Code of Canada, the sentence to be imposed on a person convicted of second degree murder is a term of imprisonment for life without eligibility for parole until the person has served at least 10 years of their sentence. However, s. 745.4 of the Criminal Code provides that the sentencing judge may increase the parole ineligibility period from 10 years up to a maximum of 25 years having regard to:

a. the nature of the offence and the circumstances surrounding the commission of the offence;
b. the character of the offender; and
c. the recommendation, if any, of the jury.

[7] As a general rule, the period of parole ineligibility shall be for 10 years. However, this can be ousted by a determination that according to the s. 745.4 criteria, the offender should wait longer before having his suitability for release assessed. Parole ineligibility is a fact sensitive process. A sliding scale of parole eligibility following a conviction for second degree murder recognizes that “there will be a broad range of seriousness reflecting varying degrees of moral culpability” with respect to this offence.

[8] In assessing the s. 745.4 criteria and deciding whether to increase the period of parole ineligibility, all objectives of sentencing are relevant, including s. 718 of the Criminal Code.

[9] As set out in s. 718 of the Criminal Code, the fundamental purpose of sentencing is to contribute to respect for the law and the maintenance of a just, peaceful, and safe society by imposing sentences with objectives that include denunciation, deterrence, rehabilitation, the promotion of responsibility, and the acknowledgement of the harm that criminal activity does to victims and to our community. However, the statutory 10-year minimum ineligibility period limits the weight that can be accorded to the offender’s prospects of rehabilitation.

[10] Regardless of the period of parole ineligibility imposed, the sentence remains one of life imprisonment. The sentencing judge does not decide when the offender should be paroled, but merely the period he or she must serve before parole can be considered.

The Nature and Circumstances of the Offence

The Facts

[11] In considering whether to increase the period of parole ineligibility, I am required to consider the nature of the offence and the circumstances surrounding it. The facts giving rise to the conviction were provided by way of an Agreed Statement of Facts which may be summarized as follows:

a. On Saturday, March 25th, 2023, the 16-year-old victim, Mr. Gabriel Magalhaes (hereinafter referred to as “Gabriel”), attended the TTC Keele Station, at 21 Keele Street, in the City of Toronto. He was on his way home and awaiting the arrival of the train with his friend, Joshua. They were seated on a bench located on the ground floor level of the subway station.

b. At approximately 8:53 p.m., Mr. O’Brien-Tobin walked down a set of stairs near the bench where Gabriel and Joshua were seated. Mr. O’Brien-Tobin had been carrying a backpack which he moved to his front shortly before walking down the stairs. Mr. O’Brien-Tobin turned. He stared at Gabriel and Joshua as they sat on the bench, unaware of him. This was captured on surveillance cameras.

c. Mr. O’Brien-Tobin then briefly exited the subway station, watching Joshua and Gabriel through a set of automatic doors. He reached into his knapsack and then came back into the subway station. He walked immediately toward Gabriel. It was approximately 8:54 p.m.

d. Unprovoked and with no exchange of words, Mr. O’Brien-Tobin stabbed Gabriel in the chest with the knife. He then walked away, exiting the subway station.

e. Gabriel collapsed on the floor. Joshua and two bystanders attempted to provide first aid until the paramedics arrived. Gabriel was rushed to the hospital. Tragically he succumbed to his injuries at 9:46 p.m.

f. An autopsy revealed that the single stab wound to the chest injured Gabriel’s left lung, pericardium and heart, causing his death.

g. Officers attended the scene and began searching the surrounding area.

h. At approximately 9:37 p.m., Mr. O’Brien-Tobin attended a church on Roncesvalles Avenue. He spoke to a priest and another member of the parish. He was acting strangely and told them he felt like killing someone. They became concerned and escorted him out of the church about 20 minutes later.

i. Approximately 20 minutes after leaving the church, Mr. O’Brien-Tobin went to St. Joseph’s hospital at 30 The Queensway. He was subsequently located by police sitting in the emergency room. He was arrested.

j. Mr. O’Brien-Tobin’s backpack was seized and forensically examined. Blood on one of the inner compartments was found to belong to Gabriel. The knife was never located.

k. A forensic examination was conducted on Mr. O’Brien-Tobin’s cellphone. An extraction of the phone revealed that Mr. O’Brien-Tobin was sending messages to his girlfriends, friends, and mother both before and after the murder. Three of those messages sent were as follows: “someones [sic] dying TN”; “I just stabbed someone random”; and “I stabbed someone and got away with it”.

Victim Impact

[12] In considering the nature of the offence and the circumstances surrounding it, I also consider the impact of this murder on the Magalhaes family and our community. In this case, Victim Impact Statements were filed. The following is an overview of their content:

Andrea Magalhaes is the mother of Gabriel. She states that her life will never be the same. She is not “able to take a single breath without feeling the sharp blade” that entered the body of her son. She says that it cuts open her soul, “leaving all the shattered pieces of my formerly merry self splattered” around her. She describes that she has become a ghost, a shadow, an empty shell. Every step is a struggle. Living is a struggle. It seems impossible for her to parent her living son. She is unable to see even a shadow of a light at the end of a tunnel. She states, “My peaceful, kind-hearted, hopeful, extremely hardworking, loving, and beloved son will never get to follow his dreams.” That kills her inside. She feels that she has failed because she was unable to keep her son safe.

Antonio Fernando De Magalhaes is the father of Gabriel. He describes a life where he and his wife were planning for their son’s future. Saving for his education, ensuring that he had what he needed to achieve his goals and dreams. On March 25, 2023, his life changed from a perfect dream to a nightmare. He has difficulty interacting with others. Even the simplest things are difficult. He fears for his living son. His life has been forever changed. He describes that his “nightmare will only end the day that I am at peace beside my Gabriel”.

Marcia Magalhaes is Gabriel’s aunt. She states that it is difficult to talk about the impact of her nephew’s death. Her world, as she knew it, has changed forever. The unbearable pain continues. She says that the suffering of her family “is impossible to describe”. She observes that the impact of Gabriel’s death on his immediate family is “permanent”. The family will never “again live peacefully”.

Daniel Montgomery is an employee of the TTC. He explains that he was the first on scene and found Gabriel after the stabbing. He observed the wound after removing Gabriel’s clothing. He spoke to Joshua, who he describes as courageous. He has suffered greatly. After the stabbing, he was confined to his apartment, leaving it only to purchase groceries. His personal relationships were strained. He became isolated and did not work for 18 months. He remains under the care of a psychologist. Upon returning to work, he became hyper vigilant about his surroundings and has purchased a “stab proof” vest to protect himself. He continues to pray for Gabriel.

Pat Caramuto was an employee at the TTC Keele Street Station at the time of the stabbing. He describes that the incident “screwed” him up emotionally and that he distanced himself from others. He feels angry that a child died senselessly on his watch. As a result of this offence, he describes that he has changed. He is vigilant and watches people more closely. He has lost his trust and has concerns for others in the station.

[13] There are several aggravating factors about the nature of the killing and the circumstances of the offence. These aggravating factors include the following:

a. Gabriel was a 16-year-old who was with his friend at a subway station. They were doing what any member of our community is entitled to do: waiting for a subway train to take them home on a Saturday evening.

b. There was an element of planning and deliberation involved in this matter. The Agreed Statement of Facts indicates that Mr. O’Brien-Tobin was sending text messages before the stabbing. Amongst other things, he forecast that someone was dying that night.

c. Mr. O’Brien-Tobin attended at the TTC station armed with a knife to affect his purpose.

d. Mr. O’Brien-Tobin first stared at Gabriel, who was a stranger to him. He briefly exited the station but watched Gabriel and his friend Joshua though a set of doors. He reached into his knapsack. One minute after first observing Gabriel, Mr. O’Brien-Tobin returned and walked immediately towards him.

e. Unprovoked, Mr. O’Brien-Tobin stabbed Gabriel in the chest, causing his death.

f. Gabriel was unarmed, vulnerable and defenceless.

g. Mr. O’Brien-Tobin walked away from the incident, providing no assistance to Gabriel before he did so.

h. Other members of our community and Joshua provided first aid to Gabriel before paramedics arrived. This incident, no doubt, caused them to be traumatized.

i. Mr. O’Brien-Tobin was clearly aware of the nature and consequences of what he had done at the time. He knew it was wrong. After the murder, he indicated to persons, through messages, that he had just stabbed “someone random” and that he had stabbed someone and “got away with it”.

j. At the time, Mr. O’Brien-Tobin showed absolutely no remorse for his conduct and appeared boastful of his heinous act.

k. The murder of Gabriel has had a devastating effect on his family. No one deserves such a fate.

l. Gabriel’s murder has also affected others, including the TTC employees who were present. They, too, have been traumatized.

m. The murder of Gabriel, in a public TTC station, profoundly shocked our community. Those who ride the TTC to get to work, meet with friends and attend other events may be left to wonder, “Am I next?”.

n. The murder of Gabriel has led to a deterioration of the public’s sense of security in the TTC.

[14] Based on a consideration of the nature and circumstances of the offence, I find that this factor warrants an increase in parole ineligibility.

The Character of Mr. O’Brien-Tobin

[15] The next statutory consideration is the character of the offender, Mr. O’Brien-Tobin.

Personal Background

[16] Mr. O’Brien-Tobin’s background was provided, in part, in a pre-sentence report. It may be summarized as follows:

a. Mr. O’Brien-Tobin was born in St. John’s, Newfoundland, on June 30, 2000. His parents separated shortly after his birth. Mr. O’Brien-Tobin resided with his mother and had limited contact with his father.

b. Mr. O’Brien-Tobin’s mother (Ms. Jennifer O’Brien) advised that Mr. O’Brien-Tobin’s father struggled with alcohol addiction and was physically, financially, and emotionally abusive. Mr. O’Brien-Tobin’s grandfather became a father figure and the two were described as inseparable. His grandfather’s passing was a traumatic event for Mr. O’Brien-Tobin.

c. Child and Youth Services was involved in Mr. O’Brien-Tobin’s life.

d. Mr. O’Brien-Tobin was not abused by his mother. He was, however, sexually assaulted by one of her partners between the ages of five and nine.

e. Mr. O’Brien-Tobin’s mother described that as a child and teenager, Mr. O’Brien-Tobin was violent and struggled to control his behaviour. He acted out by “kicking, punching and spitting”. He was impulsive, irrational and could not remember things.

f. At the age of eight, Mr. O’Brien-Tobin had a mental health assessment. He was diagnosed with attention deficit hyperactivity disorder (ADHD), depression, oppositional defiance disorder (ODD) and bi-polar disorder. Prescribed medications only pacified Mr. O’Brien-Tobin.

g. Although Mr. O’Brien-Tobin had difficulties in school and was suspended many times, he did finish his elementary education. His violent conduct in school resulted in the school having to lock down because of his behaviour. He reports that he completed a few high school courses. He intends to complete his high school education while serving his sentence.

h. In 2011, Mr. O’Brien-Tobin was removed from his mother’s home and placed in a group home until the age of 17. His violent tendencies continued there when he pushed a staff member down the stairs. His mother describes that Mr. O’Brien-Tobin “gave up on everything good in his life” when he lived at the group home. It is at this point, that he was repeatedly involved in the criminal justice system. He violated his curfew countless times.

i. On occasion, Mr. O’Brien-Tobin would attend at his father’s residence. It has been suggested that his father was a bad influence because he normalized violence. Mr. O’Brien-Tobin’s father told him that it was normal to get into fights with others and be involved in the criminal justice system.

j. At the age of 17, Mr. O’Brien-Tobin left the group home. He returned to his mother’s home. His violent tendencies continued, abusing his stepfather, and refusing to abide by the rules of the home.

k. Mr. O’Brien-Tobin moved to his own apartment when he was 18 years of age. However, his substance abuse and violence led to the destruction of the unit.

l. In 2020, Mr. O’Brien-Tobin started collecting the Canada Emergency Response Benefit (CERB) which provided funds for him to relocate to Ontario. The change of location did not assist him in leading a pro-social life. He quickly engaged with the criminal justice system here.

m. Mr. O’Brien-Tobin is not married but claims to be the father of five children. He says that two reside in Newfoundland and he is the father of triplets in Ontario. Mr. O’Brien-Tobin’s mother believes he has one child in Newfoundland that she is aware of. She believes that the triplets are a figment of her son’s imagination. He could not provide any contact information for the mother of the triplets so that this could be confirmed.

n. Mr. O’Brien-Tobin has been sporadically employed in the construction business. He is unable to maintain any commitments due to his limited attention span, poor attendance, lack of patience, and a tendency to become easily frustrated.

o. Mr. O’Brien-Tobin has a history of substance abuse that commenced at age 13. He has used oxycodone, crack cocaine, Zanax, LSD, MDMA, heroin and marijuana. He disclosed that at the time of this offence, he was using “a little bit of everything”, including methamphetamine.

p. Mr. O’Brien-Tobin says that he has attempted to commit suicide several times by cutting himself, overdosing, and jumping in front of a subway car.

q. When asked by the probation officer about the offence before the court, Mr. O’Brien-Tobin described it as a “big waste of time”. During the sentencing hearing, counsel explained that what Mr. O’Brien-Tobin meant is that “all of this could have been avoided but for his actions”. He did not mean that the “process” is a waste of time.

Community Support

[17] Filed at this proceeding, was a letter by Mr. O’Brien-Tobin’s mother, Ms. Jennifer O’Brien. It was lengthy and gives some insight into his history. It confirmed much of the content of the pre-sentence report including reference to Mr. O’Brien-Tobin’s turbulent relationship with his father who was less than supportive in the upbringing of his son.

[18] Various resources in Newfoundland were accessed to help deal with Mr. O’Brien-Tobin’s challenges, including the Janeway Psychiatric Assessment Unit, and Child, Youth and Family Services, as well as social workers. Big Brothers was accessed to fill the void left by Mr. O’Brien-Tobin’s father and other male role models being unavailable. Ms. O’Brien enrolled her son in organizations such as the Pioneer Club through the Salvation Army. He played Timbit Soccer and bowled with a youth bowling club. He raised money through the Janeway Telethon and participated in the Navy League Cadets. He took drum lessons and participated in recitals. He attended swimming lessons and was involved with the Boys and Girls Club.

[19] School was a challenge for Mr. O’Brien-Tobin. Ms. O’Brien describes that her son was “kicked out” of his daycare for “being uncontrollable”. Teachers were having difficulty because Mr. O’Brien-Tobin was unable to focus and settle. It was in grade two that Mr. O’Brien-Tobin’s mother says he was diagnosed with attention deficit disorder.

[20] At age eight, Mr. O’Brien-Tobin began seeing a psychiatrist. He was placed on medications. Unfortunately, there were several side effects. Although the medication calmed Mr. O’Brien-Tobin, he would suffer significant repercussions as the medication wore off. He would scream, yell, and hit things. The use of medications, Ms. O’Brien says, led her son to a “world of addiction and substance abuse”.

[21] Mr. O’Brien-Tobin was eventually removed from his home. Child Youth and Family Services concluded that Mr. O’Brien-Tobin could not be controlled. It was at this point that he gave up on school and missed curfew. Ms. O’Brien describes that this was a “downward spiral for Jordan as he followed a bad group thinking these people were his friends”.

[22] At age 18, Ms. O’Brien explained that her son was diagnosed with Oppositional Defiance and Bi-Polar disorders. Thereafter, he spent significant amounts of time incarcerated for various offences. He was involved in the drug trade.

[23] At the time of the Covid epidemic, Mr. O’Brien-Tobin left Newfoundland in search of a better life. However, he soon found himself in conflict and homeless. He would steal and participate in illegal activities so that he could eat. Ms. O’Brien describes that he would have psychotic episodes and suffer depression. He was suicidal.

Criminal Antecedents

[24] Mr. O’Brien-Tobin has a criminal record with entries commencing as a youth and continuing into adulthood. In total, Mr. O’Brien-Tobin has almost 200 convictions.

[25] As a youth, Mr. O’Brien-Tobin amassed 117 convictions, all in St. John’s, Newfoundland. Several convictions were for crimes of violence including assault, assault with a weapon, and uttering threats. Most convictions were offences arising out of his failure to comply with his recognizances, undertakings, and dispositions (more than 100).

[26] As an adult, Mr. O’Brien-Tobin amassed 77 convictions. Those convictions commence in St. John’s, Newfoundland. They continue across Canada with convictions in Quebec and then in Ontario, including in Newmarket, Brampton, Brantford, Milton, and Toronto. Several convictions are, again, for crimes of violence including assault, assault with a weapon, uttering threats and lastly, sexual assault. Mr. O’Brien-Tobin has incurred over 25 convictions for failing to comply with community supervision orders. He has served sentences in the reformatory for relatively short periods of time. He has never been to the penitentiary.

[27] The murder of Gabriel is not the first time that Mr. O’Brien-Tobin committed a crime on somebody who was accessing the TTC. His last conviction was for sexual assault when Mr. O’Brien-Tobin and the complainant were riding the subway. A transcript of the sexual assault proceeding provides the factual basis for this offence. Briefly, it may be summarized as follows:

a. On October 19, 2021, the complainant was riding a northbound TTC train at 9:00 a.m. As the train approached Eglinton Station, the complainant was aware that Mr. O’Brien-Tobin, from a distance, was watching her.

b. The complainant was approached by Mr. O’Brien-Tobin. He sat in the seat facing her and said, “you’re cute”. The complainant told Mr. O’Brien-Tobin that she had a boyfriend and that she was not interested in talking with him. That did not deter Mr. O’Brien-Tobin.

c. Mr. O’Brien-Tobin moved into the seat directly to the left of the complainant and tried to engage her in conversation. He began touching her upper leg. He told her that he wished to have sex with her and would pay her $400 to do so. The complainant eventually got away.

d. Mr. O’Brien-Tobin was taken to a hospital shortly thereafter. He was treated for a drug overdose. He was eventually arrested.

[28] Mr. O’Brien-Tobin pleaded guilty to sexual assault on March 10, 2023. He received a sentence of 100 days (time served) and probation. During his elocution, Mr. O’Brien-Tobin said that he recognized the seriousness of the offence and hoped to turn his life around. He planned to enter a rehabilitation centre and go to the “Metal Works Institute” to pursue a trade. He also intended to pursue his passion for music. He was going to seek permanent housing. He stated, “I’m only 22 years old and have realized that jail isn’t where I want to be any longer.” He wanted to “restart his life”.

[29] Fifteen days later, Mr. O’Brien-Tobin stabbed and killed Gabriel, giving rise to his conviction for second degree murder.

Forensic Evidence

[30] Dr. Mark Pearce, a forensic psychiatrist, was consulted to determine whether Mr. O’Brien-Tobin was eligible for an NCR defence. On May 22, 2024, Dr. Pearce provided the following opinion regarding Mr. O’Brien-Tobin:

He suffers from very serious personality pathology (antisocial personality disorder, and he’s probably psychopathic) and a severe, polysubstance use disorder. He has experienced psychotic symptoms while under the influence of substances at times, but he does not suffer from a primary mental illness. He was not rendered, at the time of the alleged murder, incapable of appreciating the nature and quality of his actions or knowing that they were wrong.

[31] Dr. Graham Glancy also saw Mr. O’Brien-Tobin on December 1, 2021 (prior to this offence), when he was incarcerated at the Toronto South Detention Centre (“TSDC”). Dr. Glancy did not diagnose Mr. O’Brien-Tobin but assessed him for a possible NCR defence and fitness for trial. His report concluded as follows:

• No issues relating to fitness to stand trial and NCR not being considered as a legal pathway, or not applicable.
• Does not suffer from a diagnosable mental illness.
• Patient has declined any further input from CAMH FEIS Programme.

Remorse

[32] By way of his plea, Mr. O’Brien-Tobin takes responsibility for the actions giving rise to his conviction which is a sign of remorse. Further, it is evident from his elocution.

[33] At the conclusion of the sentencing hearing, Mr. O’Brien-Tobin apologized to the family of Gabriel and addressed other issues as follows:

Words cannot explain the sorrow I felt when I officially realized what I had done. I will never be able to bring your friend/family member back from the dead and for that I’m truly sorry. I personally lost a friend of mine who was like a sister to me to suicide exactly 3 weeks before. She was also 16. It is due to this and other things that at the time of my arrest I was going through a lot emotionally, mentally and physically. I didn’t really realize what I did until I seen the news article and once I semi-realized I messaged the couple of people I knew could help me. Why did I stay in Toronto when it was so critical to leave? I can only assume to face the consequences of my actions. I no longer sleep at night because I am haunted by what I did. To know I took the life of such a successful person who could’ve done so many great things hurts. Saturday past, my world was turned upside down by the death of my first-born daughter. I ask myself if this is God punishing me for what I’ve done. It’s not easy losing a child and I can only imagine the pain you’re going through. My words cannot bring back your loved one, but I am very sorry for what I did and I’m sorry for your loss. Thank you.

Pre-Sentence Incarceration

Records were provided from the Maplehurst Correctional Complex and the Toronto East Detention Centre (“TEDC”). They show that Mr. O’Brien-Tobin has been incarcerated for 685 days. They also show the following:

• Maplehurst: Mr. O’Brien-Tobin was incarcerated for 544 days. He was subject to lockdowns 232 times (197 full, 35 partial). He was triple bunked for 261 days and was the subject of 6 misconducts.
• TEDC: At the time of the production of records, Mr. O’Brien-Tobin had been incarcerated there for 16 nights. He was housed in the “Medical-Supportive Care Unit” where he was let out of his cell for two hours a day. On one occasion, he did not receive the two full hours. He was offered yard time 10 times.

[34] Counsel also advised that in December 2023, Mr. O’Brien-Tobin found himself amid a small riot at Maplehurst. While he had nothing do with its commencement, he was hit with rubber bullets and pepper spray which were used to de-escalate the riot. He was subdued and strip searched which has negatively affected him.

[35] Based on the character of Mr. O’Brien-Tobin, including the circumstances in which he has lived, I find that this factor, also, warrants an increase in parole ineligibility. I am satisfied that Mr. O’Brien-Tobin represents an ongoing danger to our society.

Recommendations of the Jury

[36] The third matter that a sentencing judge is required to consider in determining whether to increase the parole ineligibility period is any recommendation made by the jury. Of course, there were no recommendations made by the jury as this matter was a plea before me.

Parole Ineligibility Parameters (The Range)

[37] As I have stated above, Crown counsel seeks a period of parole ineligibility of 18 years, and defence counsel, 12 years. Both submit that a period of parole ineligibility above the minimum is required. I agree.

[38] When considering parole ineligibility, and in addition to the principles I have already outlined, sentencing judges must also consider the principle of parity: similar offenders who commit similar offences in similar circumstances should receive similar sentences pursuant to s. 718.2(b) of the Criminal Code. Crown and defence counsel provided me with decisions in support of their positions. While I will not reference each one, I have reviewed them all.

[39] The authorities provided show that some sentences were imposed following a guilty plea. Other sentences were imposed following a judge alone or jury trial. In some instances, the offender had a substantial criminal record while in others, the offender did not. Some offenders were Indigenous. Others suffered from diagnosed mental illnesses and some from drug-induced psychoses.

[40] The case of R. v. Cheong is somewhat like the case before me. Mr. Cheong, unprovoked, pushed a stranger in front of a TTC train. Tragically, she died. He had previously pushed a woman in the path of a subway train 7 or 8 years prior. Mercifully, she suffered only an ankle injury. Mr. Cheong was not charged with an offence arising from that incident. Mr. Cheong had a history of mental illness, including diagnoses of schizophrenia of the paranoid type. He also suffered from a substance abuse disorder. That said, he was fully criminally responsible for his conduct. He seemed likely to re-offend. Watt J. (as he then was) imposed a life sentence of imprisonment without eligibility for parole for 15 years.

[41] While the nature of the offence and the circumstances surrounding the commission of the offence in Cheong are somewhat similar, the character of the offenders is very different. Mr. Cheong had been diagnosed with a major mental illness while Mr. O’Brien-Tobin has not. Further, Mr. O’Brien-Tobin is a young man who has amassed a significant criminal record, including multiple crimes of violence. Mr. Cheong had a criminal record that commenced in his thirties. For the most part, the convictions were property related. They were not for crimes of violence against others.

[42] Having considered the cases provided by counsel, including Cheong, I am mindful of Chief Justice Lamer’s caution in R. v. M. (C.A.) that “… the search for a single appropriate sentence for a similar offender and a similar crime will frequently be a fruitless exercise of academic abstraction”. What the cases show is that, ultimately, sentencing is an individualized process.

Analysis

[43] The issue before me is to determine whether the time that Mr. O’Brien-Tobin must wait before being considered for parole should be increased beyond the minimum period of 10 years. Should it be increased to 12 years as proposed by counsel for Mr. O’Brien-Tobin or 18 years as proposed by Crown counsel?

[44] In each case, where the issue of parole ineligibility is considered, the offender will be a person who, without lawful justification, has not only killed someone but had the intent to kill or meant to cause harm knowing it would likely kill. A conviction for murder will always be founded on inherently serious conduct deserving of the significant sanction of imprisonment for life. Mr. O’Brien-Tobin’s murder of Gabriel is no different.

[45] In considering the fit period of parole ineligibility for Mr. O’Brien-Tobin, I find the following to be the aggravating factors:

a. Those involving the offence itself referred to in paragraph 13 above. I will not repeat those factors here but observe that the murder was horrific and brutal.

b. The impact on the family is significant. The family has suffered the loss of a loved one which is unimaginable.

c. The impact on our community, and particularly those who use the TTC, has been unsettling.

d. Mr. O’Brien-Tobin is not a first offender, but instead has almost 200 convictions on his record.

e. The entries on the criminal record include several offences for crimes of violence. Mr. O’Brien-Tobin has shown an utter disdain for court orders. He was on probation at the time he committed this offence.

f. Two weeks after having been convicted and released from custody for sexually assaulting a rider on a Toronto subway, Mr. O’Brien-Tobin committed this murder in a TTC station. As such, this is not the first time he has committed an offence while on TTC property, and in public.

g. Mr. O’Brien-Tobin’s conduct was randomly directed at a defenseless teenager with whom he had no prior personal contact, let alone a quarrel. It was a self-centered act of violence. Had Gabriel not been there that day, somebody else’s son, brother, nephew, grandson or friend could have been the victim of Mr. O’Brien-Tobin’s senseless crime.

h. The facts suggest that this was a planned act of violence.

i. Although given the advantages that may have been available through court ordered probation, he failed to avail himself of those offerings. There is nothing to suggest that that will improve over time.

j. Mr. O’Brien-Tobin seems likely to re-offend. He is a danger to our community.

[46] In considering the period of parole ineligibility for Mr. O’Brien-Tobin, I find the following to be the mitigating factors:

a. Mr. O’Brien-Tobin has pleaded guilty, which is a sign of his remorse.

b. Mr. O’Brien-Tobin took full responsibility for his actions by his plea.

c. The plea of guilt comes at a time when the court’s resources are under stress. The plea of guilt saved four weeks of trial time and allowed another matter to proceed.

d. The plea provided certainty of result and prevented the necessity of the Magalhaes family having to relive the death of their loved one in a trial before a jury.

e. The plea also spared Gabriel’s family having their son’s death replayed in the media.

f. Mr. O’Brien-Tobin apologized to the family during his elocution.

g. Mr. O’Brien-Tobin is young. He is only 24 years of age, having committed this murder at age 22.

h. Despite his mother’s valiant efforts, Mr. O’Brien-Tobin grew up in a tumultuous environment with little or no support from his father. Resources accessed in Newfoundland, could not curb Mr. O’Brien-Tobin’s behaviour again, despite their best efforts.

i. Mr. O’Brien-Tobin’s pre-sentence incarceration conditions have been harsh.

[47] Mr. O’Brien-Tobin is a 24-year-old recidivist. Mr. O’Brien-Tobin’s criminal record and history show that he is unmanageable in our community. He is uncontrollable. He is dangerous.

[48] Mr. O’Brien-Tobin has a limited education and has not been gainfully employed at any time. He has little, or no support in the community. While young, Mr. O’Brien-Tobin shows little possibility of rehabilitation. He seems likely to re-offend.

[49] As described by Dr. Pearce, Mr. O’Brien-Tobin suffers from very serious personality pathology (antisocial personality disorder, and he is probably psychopathic). He also suffers from a severe, polysubstance use disorder. However, Mr. O’Brien-Tobin does not suffer from a diagnosed major mental illness. Mr. O’Brien-Tobin remains fully criminally responsible for his conduct.

[50] The murder of Gabriel was an act that has elements of planning and deliberation. Mr. O’Brien-Tobin was aware of the consequences of what he had done. It is clear from his texts sent before and after the offence that he meant to cause death and thereafter boasted that he thought he would get away with it. He knew it was wrong according to both the law and moral standards of our society. Mr. O’Brien-Tobin’s moral blameworthiness is high.

[51] This is a very serious offence which has had devastating consequences for several people. It was a random act of violence exacted on a 16-year-old stranger. The consequences of Gabriel’s murder are unspeakably tragic for his family. His murder has had a chilling effect on members of our community generally, and specifically those who access the TTC. It shocked our community and has made riders on the subway feel unsafe.

[52] In deciding the minimum period of parole ineligibility, the most important factor to consider is the protection of society through specific and general deterrence and denunciation of the offence. Gabriel’s murder was a senseless act. Like the death of the victim in Cheong, Mr. O’Brien-Tobin’s murder of Gabriel was “self-centred” and “cowardly”.

[53] I am satisfied that Mr. O’Brien-Tobin represents a continuing danger to our society. A sentence of life imprisonment is not only mandatory but is also manifestly fit and appropriate.

[54] In coming to my conclusion about the period of parole ineligibility, I have also considered the pre-sentence conditions of incarceration. I find that Mr. O’Brien-Tobin has experienced conditions that are more difficult or punitive.

[55] After having considered the totality of the circumstances of this case, I am satisfied that the sentencing objectives of denunciation and deterrence are met by the imposition of a life sentence with parole ineligibility above the minimum. I find that the appropriate sentence is life imprisonment with no parole eligibility until Mr. O’Brien-Tobin has served 18 years in prison.

[56] It must not be forgotten that the sentence that is to be imposed in this case is life imprisonment. The 18-year period of parole ineligibility does not mean that Mr. O’Brien-Tobin will be released on parole after serving 18 years. It only means that this is when he first becomes eligible for parole. Whether he will be released will be up to the Parole Board, and that decision will be based in part on how Mr. O’Brien-Tobin conducts himself between now and then.

The Sentence Imposed

[57] Mr. O’Brien-Tobin is sentenced to imprisonment for life without eligibility for consideration of release on parole until he has served at least 18 years of his sentence.

[58] Because Mr. O’Brien-Tobin has been convicted of an indictable offence involving the use of violence that is punishable by life imprisonment, a prohibition order under s. 109(1)(a) of the Criminal Code is mandatory. Pursuant to s. 109(2) of the Criminal Code, I direct that Mr. O’Brien-Tobin be prohibited from possessing any firearm, crossbow, prohibited or restricted weapon, ammunition, and explosive substance for life.

[59] Murder is a primary designated offence within the meaning of s. 487.04 of the Criminal Code and accordingly, in these circumstances, a DNA order is mandatory. There will be a DNA sample order made under s. 487.04 of the Criminal Code.

[60] Pursuant to s. 743.21 of the Criminal Code, I order that Mr. O’Brien-Tobin have no contact (direct or indirect) while he is serving his sentence with members of the Magalhaes family or those TTC employees involved.

Kelly J.
Released: February 28, 2025