This presentation chronicles 200 years and more of bad behaviour, murder, bootlegging, infidelity, fatal dues and riots in the street of Toronto.

Over the years Toronto has been given the nickname of “Toronto the Good”, because of our city’s supposed lack of any sinful behaviour. But there are all sorts of scurrilous stories in Toronto’s past, if you only know where to look. This presentation will introduce you to some of the skeletons in Toronto’s historical closet. Some of the cases included in this talk include the following.

THE 1800 DUEL BETWEEN JOHN SMALL & JOHN WHITE. One of these luminaries was the clerk of the province’s executive council, and the other was no less a personage than the Attorney General. However, their wives fell out, and there were acrimonious allegations of adultery. The quarrel came to a head at a Christmas party in 1799, and a few days later, White and Small faced one another with pistols. One man would walk away under a cloud of scandal, while the other one wound up dead, and never walked anywhere ever again.

THE MURDER OF THE LIGHTHOUSE KEEPER. On a solitary point across the harbour, at the Toronto Islands, there stands a lighthouse that has looked over the lake for more than two centuries. The first keeper of the lighthouse met a bloody end, when his bootlegging business turned sour, and he was dismembered by angry customers. It’s every entrepreneur’s worst nightmare, and perhaps the ghostly legend that goes with the story will give you nightmares, too.

THE PARKDALE MYSTERY. On an autumn night in 1894, young Frank Westwood was shot to death on his front doorstep on Jamieson Avenue. Police spent months searching for the culprit of this apparently inexplicable murder in vain. Then, a mysterious woman entered the story. She had been hard to identify, because of her penchant for dressing up like a man. However, she was known to police because she’d been previously arrested for impersonating a university professor, a clergyman, and a police constable. The story of the Parkdale Mystery is probably the most bizarre case to have ever been heard in a Toronto courtroom. There was even a surprise ending!

THE GRISLY STORY OF DR. H. H. HOLMES. Set against the backdrop of the bright shining lights of the Chicago World’s Fair, held in 1893, a more sinister story was unfolding. Enter Herman Webster Mudgett, better known under his alias of H. H. Holmes, who would become one of the most prolific serial killers you’ve probably never heard of. Over a period of about six years, he murdered 27 victims. Well, those are the number that he confessed to. Some crime historians have estimated that he might have killed as many as 200 people. Although much of his story was set south of the border, it was his nefarious activity in Toronto that led to his capture. This is a crime story that is not for the faint of heart!

THE MASSEY MURDER. The Massey family was one of the most pre-eminent families in Toronto’s history, but every family has secrets to keep. Charles Albert Massey, known to his friends as “Bert”, was a family outsider who liked fast cars and fast women. His wife was away one winter’s evening in 1915, and Bert Massey got a little too close for comfort with a young woman who didn’t share his enthusiasm. Bert Massey would pay with his life, and the young woman that he accosted would be at the centre of one of Toronto’s most famous court cases.

These are just a few of the compelling True Crime stories from Toronto’s past that we can present. If you enjoy “True Crime” you can also have a look at the presentations on the Boyd Gang, as well as the one on the History of Policing and Prisons in Toronto.