Accused in crossbow killings robbed banks after racking up debt in romantic relationships

The man charged with killing his mother and two brothers in the so-called crossbow slayings turned to robbing banks in 2009 to pay more than $60,000 in debts he'd largely accrued in two romantic relationships, according to parole and bankruptcy documents.

Brett Anthony Ryan, 35, was diagnosed with depression when he had psychological counselling during the 15 months he spent in jail and reports said depression over his debt burden was a factor in the robberies. Before he was released on day parole in April 2010, he was termed an apparent model prisoner who was considered at low risk to re-offend, Parole Board of Canada documents show.

A psychiatric report entered into his January 2009 sentencing hearing found that he showed no signs of aggression or violence, but a psychologist noted in jail that he'd had issues with unhealthy romantic relationships.

Ryan now stands charged with three counts of first-degree murder in east Toronto, charged exactly three weeks before he was to be married.

The couple met before Ryan's parole would have ended. He would have had to report the relationship to his parole supervisor as a condition of his release, because the board considered a past breakup a trigger for the robberies.

"The board noted that you had undergone a number of personal and financial setbacks and that, rather than being open about these factors, you chose not to share these concerns with your family or others, and believed that robbing banks was your only way out of your dilemma," a November 2010 parole decision reads. "You told the board that you had invested everything in your two previous relationships and were let down on both occasions."

Robbing 14 banks

Ryan robbed the first of 14 banks on Oct. 20, 2007, telling the parole board he felt a thrill during the first bank robberies, but later felt remorse as the eight-month spree continued across the Greater Toronto Area.

He had a rotation of different disguises, including bandages wrapped up his face or a fake beard. Some days he limped, others he presented himself as a businessman.

Each time, however, Ryan would slide a note to the teller saying he wanted them to place $2,000 or $3,000 in a bag and that he had a gun.

Police never found a firearm, however, and the Crown withdrew a weapons possession charge against Ryan along with 12 other robbery-related offences when he pleaded guilty on Jan. 26, 2009.

He told police he never carried a gun; when he was arrested officers found pepper spray on him. He reported "feeling relief" when he was caught, the parole documents show.

Ryan told the board that he regretted what he had done and understood that he'd inflicted psychological trauma on the bank employees he'd targeted.

Records showed that he stole about $28,000. Most of that was never recovered, the parole documents show.

Diagnosed with depression

Ryan began counselling in jail, something that he was ordered to continue as a condition of his day parole. He still had the stress of more than $60,000 in debt hanging over him and the board noted that he needed to work on his "financial stressors" on his release.

Although a psychiatric report at his sentencing hearing found that he was at risk "for developing a more serious form of depression" because it ran in his family, it found no evidence of psychopathic behaviour, personality disorders or aggression or any other significant mental illness.

The psychologist Ryan saw in jail recommended he would be a good candidate for a day parole, provided he continue counselling. He would need help to "manage emotional and relationship issues" within his family and intimate relationships and other "reintegration stressors," the decision reads.

While in jail, however, Ryan reconnected with his family after an unknown period of estrangement. They helped pay off some of his debt and there was a possibility his family would help him pay for two summer university courses if he were released on day parole, according to the board.

"You told the board that previously you would withdraw and shut down, resorting to "Band-aid" solutions to deal with your depression, but now you communicate with family and supports," the decision reads. "You have spent significant time re-establishing these relationships since your incarceration [and you said] that there has been significant progress in this regard."

Ryan's mother, Susan, his father and one of his brothers attended his hearing for day parole in April 2010.

His father, William, died within the last two years, property records show. His mother died from strangulation last Thursday, while two of his three brothers were killed with a crossbow bolt and an arrowhead at their mother's home on Lawndale Road in Scarborough.

Full parole

Ryan was released to a halfway house in May 2010 where he picked up a part-time job at a restaurant, earned weekend passes, and signed up for university courses.

Six months later, he was given full parole after declaring bankruptcy and an intention to complete his biophysics degree while working part-time.

During that November 2010 parole hearing, Ryan's psychologist noted that he no longer needed counselling. He did, however, still need to tell his parole officers of any new relationships given that his past breakup had been considered "a significant stressor."

It's unclear exactly when Ryan met his fiancée.

A post on her Facebook profile in September 2012 announced they were marking their one-year anniversary, a milestone celebrated by several friends who left comments. Another picture — of roses, a framed photo and a book marked Our Story — was posted in September 2013, indicating they were celebrating their second anniversary.

There's no indication in the parole board documents whether Ryan reported the relationship to his parole officer.

He and his fiancée had been set up for their first date, according to the couple's wedding website, which was recently taken down.

They would have been married Sept. 16.