Toronto Crime Tours: Recent Episodes
Toronto Crime Tours
We are Toronto Crime Tours, the only crime tour in Canada hosted by former Detectives. From our downtown, east end and west end tours, all of which have 15 stops, we present 5 of the more strange stories we present on the tour.
Toronto was a very different city in 1939. The seediest place in town was Jarvis & Dundas, "The Corner". Scruffy bars and hotels could now sell beer by the glass, and the clientele was on rougher side. Bookmaking was a flourishing illegal trade, and The Corner was full of thugs who were quick to strong arm those who wouldn't settle up their bets. Jimmy Windsor owned a few bars in the area. A flashy, confident man, he wore lots of jewelry and always had a stack of bills to proudly display. One night, Jimmy was having dinner with family in Midtown Toronto, when 4 robbers burst into the house brandishing guns. It was a robbery, but Jimmy was taken aback by the gun toting men barging into his home. He froze, which angered the gunmen, who shot Jimmy in the stomach, killing him. They stole his jewelry and fled. The town was in an uproar, with headlines blaring "Is US Mob Style Violence Coming To Toronto?". Hear how the crime shook the police into further cracking down on bookmaking, and the sensational trial of Mickey McDonald, known as the Mad Dog of Jarvis Street.
Norman "Red" Ryan grew up in Toronto's Parkdale/Trinity Bellwoods area in the 1920s. He progressed quickly from a small time crook to an international bank robber. After numerous stints in Kingston Penitentiary, including a rare escape from the fortress like prison, Red Ryan began to turn his life around while serving a life sentence. He repented his crimes, lectured fellow inmates about the perils of a life of crime, and convinced authorities he was a model inmate for the newly emerging prison reform movement, which sought to give parole to offenders. Prime Minister RB Bennett had a personal visit with Ryan, and later signed his "ticket of leave" release. Upon release, he was a "celebrity ex-convict". He was seen at social events and hung out with pro athletes and business owners. However, he was living a double life: Red Ryan returned to his old ways of robbing banks. Hear of the dramatic end of his story during a liquor store robbery in 1936.
The shocking and scandalous murder of Charles "Bert" Massey, of the wealthy, high society Massey family, led to the Trail Of The Century. Hart Massey built a wealthy farm equipment company., and is the family name behind Massey Hall. His grandson, Bert, was from a part of the family that was not privy to the Massey's wealth. Carrie Davies was Bert Massey's live in servant. Bert had allegedly made physical advances upon his servant, who feared her reputation would be ruined. As Bert returned to his Toronto home on February 8th, 1915, his maid met him at the front door and exclaimed "you've ruined my life!". The ensuing trial gripped the city and the entire country, each day of the trial being front page news. Listen to how the courtroom drama unfolded and shocked the city with its verdict.
welcome to Toronto Crime Tours, the only crime tour in Canada hosted by former Detectives. Our 3 tours, east end, west end, and downtown, all have 15 unique stops. From these 45 stories, we present to you the 5 most bizarre crimes in Toronto's history.