Accused in Keele subway TTC killing violated probation orders, documents reveal

Open this photo in gallery:

One year before this spring’s fatal stabbing of a teenager at the Keele subway station in Toronto, the man charged with that crime was in jail. And he was facing more than 70 criminal charges.

But Jordan O’Brien-Tobin, now 22, was about to receive a deal. On March 31, 2022, at Toronto’s Old City Hall court, he entered into a plea bargain for his release under a probation order.

Defence and prosecution lawyers had agreed. Because the accused had already spent significant time in jail after his arrests, pending charges against him – involving theft, fraud and drugs – were withdrawn or resulted in suspended sentences. In exchange, Mr. O’Brien-Tobin pleaded guilty to many of the charges, including assault with a weapon. He was released on time served after committing to the standard promise to keep the peace and be of good behaviour.

“You will be placed on probation for a period of two years, That’s 24 months. Are you listening, Mr. O’Brien-Tobin?” asked Ontario Court of Justice judge Malcolm McLeod. “Yes I am,” the accused replied over a video feed from a detention centre.

The terms of the order state that any conviction for a breach of the probation could cost Mr. O’Brien-Tobin up to four more years in jail. He also had to stay away from the stores where he had been caught shoplifting, as well as from several security guards and retail clerks he had assaulted. Weapons, too, were forbidden, including “any sharp implements, including knives.”

TTC stabbing victim Gabriel Magalhaes remembered as an adventurous thrill-seeker who was always smiling

But Mr. O’Brien-Tobin did not keep the peace. He went on to commit at least three more violent assaults, including one with a boxcutter.

He was convicted and sentenced for those crimes, however prosecutors and judges never followed through on the threat to impose a years-long jail sentence if he violated the March, 2022, probation order. Court documents and audio recordings obtained by The Globe and Mail reveal only shorter stints in custody followed by more releases, more probation orders.

Mr. O’Brien-Tobin was charged late last month with first-degree murder in the death of Gabriel Magalhaes, a 16-year-old boy, who was stabbed to death while siting at a subway stop.

The fatal stabbing followed other high-profile incidents of violence on Toronto’s transit system and happened amid a debate about whether courts are too quick to release repeat violent offenders.

The Globe obtained audio recordings from four sentencing hearings involving Mr. O’Brien-Tobin’s assault convictions from the past year. The recordings reveal escalating violence by a young man who was homeless and addicted to drugs – and who did not keep his promises to the courts.

Maher Abdurahman, a spokesman for Ontario’s Attorney-General, declined to comment on Mr. O’Brien-Tobin’s cases because he is still before the courts.

Mr. O’Brien-Tobin was raised in Newfoundland. He came to Toronto in July, 2020, where he got into constant trouble.

In April, 2021, he was arrested for several crimes including an assault on an employee at a big-box store in Toronto’s West End.

“Someone has got to step in and say, ‘Enough is enough,’ ” Mario Shelton, the victim in that attack, told The Globe.

Mr. Shelton recalled that he smelled smoke wafting out from the locked door of a nursing room for mothers. He knocked and told the person inside to leave. That’s when Mr. O’Brien-Tobin came out of that room with a crack pipe and glazed eyes – and then, flying fists.

“I kept ducking and moving,” said Mr. Shelton. He said he was not seriously hurt, even though the larger man was “wailing” on him with more than 30 swings up and down grocery aisles.

Fighting or fleeing is no answer

Later in 2021, there were similar assaults at other stores. That September, he threw a pair of scissors at a security guard, defence lawyer Robert Cutruzzola said during a legal proceeding last year. Mr. Cutruzzola also referenced a “minor stabbing” by his client where “minimal injuries were suffered.”

All this was a prelude to the March 31, 2022 hearing at Old City Hall known as a global sentencing resolution to deal with all the charges Mr. O’Brien-Tobin had been racking up in Toronto, Mississauga and Brantford, among other jurisdictions.

The suspended sentences and withdrawn charges included several alleged assaults – including the attack on Mr. Shelton – as well as dozens of charges that Mr. O’Brien-Tobin had breached conditions and probation orders imposed on him in past sentencings.

Records show prosecution and defence lawyers agreed that the 204 days Mr. O’Brien-Tobin spent in jail after his many arrests could be considered akin to a 500-day jail sentence. Justice McLeod agreed to the joint proposal for a probation order.

Three weeks later, on April 17, 2022, Mr. O’Brien-Tobin was lying inside the doorway of a high-rise on Elm Street, when a security guard told him to leave. He punched the security guard in the head, according to a court recording. He also threated to stab the guard with a knife.

Mr. O’Brien-Tobin was released on bail after five days. Later that month, he stole a 32-inch Samsung TV from a Walmart in Richmond Hill and took a swing at an employee who tried to stop him. During that arrest, he told authorities he had just consumed 20 pills and was concealing a bag of fentanyl.

Last summer, he pleaded guilty to both of these crimes. During a June hearing in Newmarket, he was given a 90-day jail sentence, as well as a three-year probation order with a condition to stay out of all Walmarts in Ontario.

“You’ve been on probation before, sir, but I’m hoping that now that you’re a bit older that you’ll take the probation seriously – because that will be the way that you will get yourself back on track,” said Justice Simon Armstrong.

Last August at Old City Hall in Toronto, Mr. O’Brien-Tobin got a 45-day jail sentence and 12 months of probation for the assault on the security guard. Justice Victor Giourgas told Mr. O’Brien-Tobin that he had to work closely with a probation officer and line up drug counselling.

In September, Justice Sandra Caponecchia meted out a 150-day jail sentence for assault with a weapon for another crime.

Mr. O’Brien-Tobin had barricaded himself in a Boston Pizza washroom in Mississauga. When a manager asked him to leave, he lunged with a boxcutter. Police arrived and tasered him.

During that hearing, Justice Caponecchia told Mr. O’Brien-Tobin that the court appreciated his guilty plea – but he had “many, many breaches of court orders.” Records show she convicted him of breaching his weapons prohibitions. A charge that he violated his March 31, 2022 probation order was withdrawn.

“The public will be at risk if he doesn’t get the rehabilitation that he so clearly needs,” Justice Caponecchia said. She imposed new conditions for his eventual release. “You’re making an appointment to see a doctor and going to see that doctor every month for 18 months of your probation.”

Systemic problems exist in Ontario in the administration of probation orders, according to critics. For example, union officials representing probation officers say that workloads in the province are the highest in Canada and that recidivism rates are the highest, too. These officials also say that prosecutors are not pursuing breach-of-probation charges in court like they used to.

“We’re seeing increasing numbers of our breach packages being withdrawn by the Crown,” said Scott McIntyre of the Ontario Public Service Employees Union.

“You’ve got to scratch your head and ask why aren’t they being incarcerated for the breach?”

With a report from Stephanie Chambers