A 22-year-old accused of fatally stabbing a teenager at Keele Station over the weekend was released on a probation order just weeks earlier, tied to a sexual assault charge, court documents show.

The court documents obtained by CTV News Toronto chronicle years of criminal charges filed against Jordan O’Brien-Tobin throughout the short duration of his adult life. Thefts, threats, assaults with a weapon and continuous failures to comply with probation orders are just a number of the interactions he has had with the criminal justice system since he’s become of legal age.

On Saturday night, O’Brien-Tobin allegedly killed 16-year-old Gabriel Magalhaes in what police are calling an “unprovoked” attack while the teenager was sitting on a bench in the station. The accused of no fixed address was subsequently arrested and charged with first-degree murder.

Just weeks earlier, on March 10, an Ontario judge sentenced O’Brien-Tobin to a two-year probation order for a sexual assault that took place in October 2021 and a failure to comply with a release order in April 2022.

O’Brien-Tobin was also charged with mischief for damaging an ankle monitor and assaulting a police constable in October 2021. A few months later, in May, he faced charges of sexual assault, assault, theft and uttering death threats.

Less than a year later, the accused was sentenced to 36 days in a Toronto jail paired with 12 months of probation after his release for assault and uttering threats to cause bodily harm. That September, he was sentenced to another 30 days in custody.

jordan o'brien-tobinThe 22-year-old has been involved in more than 20 criminal matters at just one Toronto courthouse, along with being ordered to stay away from a dozen businesses and a handful of people.

His criminal history also spans outside of the province of Ontario. For nearly two years, a warrant has been issued in a Newfoundland courtroom after he allegedly broke a probation order in connection with a number of charges laid against him in 2020.

The conditions of his most recent probation order included counselling for substance abuse and sexual boundaries, along with prohibiting contact with the sexual assault victim and the possession of any weapons.

Court documents did not address the judge's justification for signing off on the latest probation order, following the accused’s history of non-compliance.  

With files from CTV News Toronto's Beth Macdonell.