Inside the trail of offences that allegedly ended in an ‘unprovoked’ killing on the TTC

Inside the trail of offences that allegedly ended in an ‘unprovoked’ killing on the TTC

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Fifteen days before 16-year-old Gabriel Magalhaes was stabbed to death at Keele Station, the man allegedly responsible spoke in court.

“I want to straighten out my life,” 22-year-old Jordan O’Brien-Tobin told Judge Cidalia Faria on March 10, reading from a letter he had written during his sentencing hearing. He was appearing in courtroom 308 of the one-floor North York courthouse at 1000 Finch Ave., joining by video from the Toronto South Detention Centre, where he had been for the last five days.

Homeless, addicted to MDMA, cocaine and Xanax, and taking prescriptions for psychosis, depression, anxiety, night terrors and an addiction to opioids, O’Brien-Tobin described plainly his challenges and how he wanted to improve. He needed to apply for provincial financial support and get help finding permanent housing. He also hoped to go to a residential rehabilitation program for his addictions, he told the judge.

“I’m only 22 years old and have realized jail isn’t where I want to be any longer,” he said, adding he hoped to “actually restart my life.”

Little over two weeks later, a teenager is dead, the Magalhaes family is at a loss for why their son was taken so violently from them, and the city is on edge over the latest in a series of fatal attacks on the TTC.

Since March 25, when O’Brien-Tobin was accused of randomly stabbing the 16-year-old as he sat on a bench with a friend, the Star has pored over hundreds of pages of court records and transcripts to piece together his complex criminal history and to try to understand what went wrong. Gabriel, his family earlier told the Star, was shy and sweet, loved snowboarding and hoped to study astrophysics after high school. He had dreams, they said.

What the records reveal is how someone even the courts believed to be a possible danger to the public without rehabilitation was frequently released and rearrested while left to navigate a complicated system of mental health programs with limited support or direction.

Taken together, the records paint a picture of a justice system that appeared acutely aware that O’Brien-Tobin posed a public risk if he did not get urgent treatment, but couldn’t prevent an alleged murder.

The homicide charge against O’Brien-Tobin has not yet been tested in court and he remains in custody.

Though political officials, including Ontario Premier Doug Ford, have focused their advocacy on federal bail reform, the records obtained by the Star suggest O’Brien-Tobin’s crimes may not have been stopped by the proposed changes. Instead, legal experts say his case points to the need for more robust and available mental health supports inside the justice system and in the community — touching systems that are the responsibilities of all three levels of government, from federal criminal laws to provincial health care, correctional facilities and probation programs, to municipal shelter services and police.

O’Brien-Tobin’s story is not unique, experts told the Star.

“No matter who is incarcerated, one day they will rejoin society and either they will rejoin society better off or worse off,” said Daniel Brown, president of the Criminal Lawyers’ Association.

“Lengthy periods of incarceration and no programming on the front end … or treatment on the back end is leading to this cycle of criminality.”

A history of crimes, childhood trauma and mental health diagnoses

According to the court records, O’Brien-Tobin was born in Newfoundland as the only child in a family where he was the victim of and witness to repeated abuse.

By the age of three, his longtime lawyer Robert Cutruzzola recently told court, the boy was already being “monitored” by psychologists. At age five, he was diagnosed with “numerous developmental and behavioural challenges” including “deviance and aggressive acting out.” By age nine, that behaviour resulted in diagnoses of ADHD and oppositional defiant disorder, and he was prescribed multiple medications.

“Often doctors seemed to be experimenting to see what would work for him,” Cutruzzola said in one transcript reviewed by the Star. (The Star did not receive a response to requests to speak with Cutruzzola, who is representing O’Brien-Tobin on the homicide charge, and O’Brien-Tobin’s mother, through the lawyer.)

From ages 11 through 17, O’Brien-Tobin lived in a group home. After he turned 18, he racked up a slew of relatively minor criminal charges in St. John’s, according to records from Newfoundland’s provincial court in the span of five months, he was charged with multiple thefts from places like Sobeys, Shoppers Drug Mart, a Jungle Jim’s restaurant and a liquor store, as well as damaging property and uttering threats against a person.

Soon after, he travelled to Ontario, looking for work and hoping to start a new life, according to the court records.

But he almost immediately began committing new crimes; the Ontario court records show new charges starting in 2019 — when O’Brien-Tobin was just 19 and only newly eligible for adult punishment.

There is no central system to look up public records of criminal offenders in Ontario. Instead, reporters have called, emailed and visited courthouses in Toronto, Brampton, Newmarket, Brantford and Woodstock to try to get a clearer picture of O’Brien-Tobin’s life. That effort was not always successful. Working off each new document and a bare-bones list from the provincial ministry responsible for courts, the Star has yet to identify the dates and type of charges for more than a dozen historical cases against O’Brien-Tobin in Ontario.

The records the Star has been able to compile — nearly 30 different cases — paint a picture of a man who was constantly charged with new offences and repeatedly breaching conditions of bail or probation orders, which often overlapped with each other, sometimes several active at the same time. The information the Star was able to obtain did not always confirm whether O’Brien-Tobin was found guilty.

It is a criminal history riddled with relatively low-level or procedural offences, punctuated by at least three other unprovoked assaults that O’Brien-Tobin pleaded guilty to where he wielded or threatened to use edged weapons but did not seriously injure anyone with them.

From September 2020 to mid-2022, O’Brien-Tobin appears to have bounced between the GTA and nearby regions, his address often listed as a homeless shelter or “no fixed address.” In at least 22 separate cases during that period — with charges ranging in severity from failing to comply with probation orders to theft to assault — O’Brien-Tobin never went more than four months without appearing in a court for a new alleged offence. His longest periods between charges appear to line up with lengthier stays in custody.

In October 2021, he was arrested for another incident on the TTC. Coincidentally, it was for this case that he would return to court two weeks before Magalhaes’s alleged murder at Keele Station.

According to an agreed statement of facts, O’Brien-Tobin approached a woman on a northbound TTC subway train leaving Bloor Station. He told her she was “cute” and “repeatedly” touched her upper leg. He also offered to pay her for sex and tried to grab her phone. The two struggled and she called out to attract attention, eventually joining a group of other female passengers who escorted her to help once at Finch station.

Meanwhile, O’Brien-Tobin was taken to hospital for a drug overdose. There, he was recognized by a police officer as being wanted for the sexual assault.

On this charge, O’Brien-Tobin spent a total of 100 days in jail in between periods of release on bail pending a possible trial. But over the next year-and-a-half before he was eventually sentenced last month, he was arrested again and again and again on other offences.

The list of offences is dizzying — over a one-week period in April 2022, he falsely reported to police that a woman had stolen an illegal gun from him in Brampton; he was charged in Brantford for theft under $5,000, for which the outcome is unknown; and he punched a security guard on Elm Street in downtown Toronto and threatened to stab him because he had been asked to leave the vestibule where he was sheltering.

For that Toronto assault, O’Brien-Tobin pleaded guilty and was sentenced to 36 days in custody and a year of probation. But he never reported to his bail program office; he was charged with failing to comply with his conditions and another warrant was obtained for his arrest.

Soon after, he was arrested in Richmond Hill for shoplifting at a Walmart and assaulting a man there. He spent another 51 days in jail ahead of a sentencing hearing where a judge gave him one further day in custody and another three years of probation.

Then, on July 10, 2022, he “lunged” at a Boston Pizza manager in Mississauga while brandishing a box cutter. For that and other crimes in Peel Region, he was sentenced that September to 220 days in custody.

This is the longest jail sentence in the documents reviewed by the Star, and O’Brien-Tobin served much of it at the Maplehurst Correctional Complex in Milton before he could face sentencing on the TTC sex assault.

He pleaded guilty to that charge and on March 10, 2023, Judge Faria took into account the by-then over 100 days he had already spent in presentence custody — a standard step in any sentencing hearing — ordering him to serve one additional day in jail and another two years on probation. The probation term included conditions to “actively participate” in treatment for substance abuse and sexual boundaries.

Faria’s reasons for sentencing have not yet been approved for release by the court.

At the sentencing hearing, defence lawyer Cutruzzola described how health problems that plagued O’Brien-Tobin as a child had followed him into adulthood, including physical ailments like asthma and hypertension, and his many mental health issues.

According to Cutruzzola, in December 2021, CAMH reported he was also suffering from an unspecified schizophrenia spectrum disorder “as well as potential other psychotic disorders” and “low-grade psychosis.”

Cutruzzola noted that a Toronto program focusing on offenders with serious mental health challenges was willing to work with his client.

It was far from the first time court had heard O’Brien-Tobin needed help for his many problems. In the Mississauga box cutter case, Judge Sandra Caponecchia had ordered him into mental health counselling, saying: “The public is at risk if he does not get the rehabilitation that he so clearly needs.”

But, like in the Mississauga case, it’s not clear whether O’Brien-Tobin ever got the treatment directed, nor whether he was able to make it to the rehabilitation program following his sentencing in the earlier TTC case.

Less than two weeks later, he was arrested for allegedly killing Magalhaes in an “unprovoked” attack.

‘No treatment plan was prepared, no release plan was prepared’

In the days since Magalhaes’s death, politicians, led by Ontario’s Doug Ford, have called on the federal government to reform the criminal bail system, arguing that it should be much harder for potentially dangerous criminals to be released into the community following an arrest.

The suggested reforms include, for example, a “reverse onus on bail” for offences involving a loaded firearm. The measure would mean an offender would have the burden of proving why they should be released rather than the current system where it’s the Crown’s responsibility to prove just cause for detaining someone ahead of trial.

It’s not clear whether those proposed reforms would have made a difference in O’Brien-Tobin’s case.

Because he had already been sentenced for the sex assault, O’Brien-Tobin was not on bail when he allegedly killed Magalhaes. This means he was not subject to typical bail conditions, such as mandatory police reporting or an order to stay at a specific address, nor did he have a surety — a person who agrees to be responsible for ensuring someone follows their bail conditions before trial.

O’Brien-Tobin was instead on probation, a type of sentence that involves community supervision by a provincial probation officer. This person is responsible for monitoring any sentencing conditions laid out by the judge and calling police to report a breach, if necessary.

The Star has not seen records that detail anything other than the conditions of O’Brien-Tobin’s brief probation. His sentencing records show that his lawyer had already been communicating with O’Brien-Tobin’s probation officer on securing mental health treatment. It is unclear if these efforts led anywhere in the 14 days between his release from custody and Malagahaes’ death.

A probation officer assigned to O’Brien-Tobin would have also been responsible for several other cases. According to the provincial website, “probation officers in 121 offices supervise approximately 32,000 probationers on any given day.”

Asked to provide details of O’Brien-Tobin’s history in Ontario’s probation and parole system, a provincial spokesperson told the Star to file a freedom of information request.

The Star also found no previous records accusing O’Brien-Tobin of using a firearm, loaded or otherwise, in the commission of any crimes, nor has he ever appeared to commit a violent offence that would have clearly warranted a lengthy jail sentence under the Criminal Code. Despite dozens of offences, none of O’Brien-Tobin’s cases were heard at Superior Court, which typically takes on the most serious of cases where lengthier prison sentences are on the table. Save administrative matters, all of his Ontario court records are at the lower provincial court level.

That’s not to say he didn’t spend significant time in jail for the more serious crimes he had committed, including his 220-day sentence for the Mississauga assault. But while in jail — despite the judge acknowledging the risk he posed — court records suggest there were few or no supports for mental health treatment.

Anita Szigeti, president of the Law and Mental Disorder Association, said it’s frustrating to see people with serious mental health issues continue to show up with new, most often minor charges — such as failure to appear, mischief, property damage and relatively low-level assaults.

A large percentage of their clients don’t have housing or a stable source of income and are dealing with underlying mental health issues, she said. They may also not have ID and therefore have no access to the Ontario Disability Support Program: “All of those things combined do contribute to constant offending.”

To Szigeti, a lot of these issues could be resolved by housing people, providing them with basic income, food security and social supports — but the status quo is “they’re just completely lost to the system.”

In O’Brien-Tobin’s case, his criminal sentences included orders to seek mental health assessment and treatment, but it’s never clear from the records if he was ever able to actually get help.

In court, Cutruzzola noted his client had not received treatment in jail and that no programs were set up for him upon his release.

“His most recent time in custody for six months, nothing was done at the institution, no treatment plan was prepared, no release plan was prepared,” he said.

That story is not unusual, said Jessyca Greenwood, a criminal defence lawyer in Toronto who focuses on mental health. People with mental health issues often don’t get any treatment at all in custody or may be in seclusion or voluntary confinement, she said. There are also limited resources to help them plan for their return to the community.

“I think it probably is true that people in our community are upset when they see someone who’s out on bail and commits an offence that’s upsetting and it offends our community standards. But what the public doesn’t see is how people with mental health issues are often not well treated in jail,” she said.

“None of those pieces helps set that person up for success when they may be struggling.”

On a recent release from custody on March 2, Cutruzzola noted O’Brien-Tobin had been ordered to attend a shelter in North York, but because there was a lack of beds in a city in the midst of an ongoing housing crisis — his spot had been given away before he was released.

O’Brien-Tobin instead went to a hospital for addiction treatment, Cutruzzola said, but he was nevertheless arrested again on March 6 for failing to comply with the order to live at the shelter.

O’Brien-Tobin faced other logistical hurdles that are common for people who face similar challenges. For example, as of March 10, he had yet to obtain an Ontario Health card — a key step to accessing various provincial supports and services. Without one, someone could have a more challenging time, for example, getting prescription medicines.

Jennifer Stone, the executive director of Neighbourhood Legal Services in the city’s downtown east, says even just getting a health card can be challenging for someone with mental health concerns — making the appointment, getting to the appointment on time and not becoming agitated in the waiting room.

“The profile is just so familiar to us.”

She said so many of their clients need case management to deal with their complex and overlapping needs — everything from precarious housing, evictions, immigration status, mental and physical health, poverty and criminality — which is hard to come by.

“We struggle to try to connect people to services,” Stone said, with long waiting lists and care that can sometimes be temporary — just months at a time — before a new program needs to be found.

At the same time, legal aid funding clinics like hers rely on money that was cut by the Ford government in 2019 — cuts she said they’ve never recovered from. Only two staff are assigned to housing files at their clinic she said, describing the challenge like “drinking out of a fire hose.”

“We’re just doing so much more with less,” she said.

Following her son’s death, Andrea Magalhaes, the mother of 16-year-old Gabriel, spoke about how she sees the problem:

“People with mental health issues need more access to services,” she said. “It’s not about just adding more security; you have to provide the tools for people with mental illness to cope with life.”

Stone, told the Star she has been thinking about Gabriel’s mother. She has twins who are 16 years old and use that subway route. One of them knew the slain teen.

“It could have easily been my family,” Stone said. “My heart goes out to her and her family.”

With files from Wendy Gillis, Dhriti Gupta and The Canadian Press

Jennifer Pagliaro is a Toronto-based crime reporter for the Star. Follow her on Twitter: @jpags

Kelly Skjerven is a Toronto-based general assignment reporter for the Star. Reach her via email: [email protected]

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