10 most notorious prisoners of the maximum security Kingston Penitentiary

It opened in 1835, and though it was men-only in recent years, it used to have women and even child inmates. The prison is slated to close by 2015.

1. Grace Marks: Employed as a maid, 16-year-old Marks was convicted in 1843 of murdering her boss Thomas Kinnear and his pregnant housekeeper, who was also his mistress. Because of her age and gender, Marks was sentenced to life behind bars, while her accomplice, stable hand James McDermott, was hanged. She was pardoned in 1873 and moved to New York state. Her life was the inspiration for Margaret Atwood’s 1996 novel, Alias Grace.

2. Marie-Anne Houde: In 1920, Houde and her husband were arrested after an autopsy on the body of her 11-year-old stepdaughter, Aurore Gagnon, revealed 54 wounds that “could only have been the result of the blows to the child’s body.” Rumours swirled that Houde was also involved in the death of Aurore’s younger brother and mother, since she had been living in the house at the time and married the father a week after his wife’s passing. Houde was sentenced to hang, but the execution was delayed so she could give birth. On July 8, she gave birth to twins. A wave of public pity coupled with a clemency campaign paid off two days before she was scheduled to die in Quebec City, when her sentence was reduced to life in prison and she was sent to Kingston. Today, Aurore Gagnon, known as “Aurore the martyred child,” remains a popular icon in Quebec.

3. Norman ‘Red’ Ryan: Also known as “Canada’s Jessie James,” Ryan was a career criminal, first charged with theft at the age of 12 in 1907. By 17, he was serving his first of many stints in Kingston for “shooting with intent.” At the outbreak of the First World War, he enlisted rather than face decades in prison but soon returned to his old ways. By the early 1920s he was an enthusiastic bank robber. Along with a gang of prisoners, he escaped from the pen and went on a crime spree that ended in Minneapolis. After returning to the pen, he became a model prisoner, and with the support of prime minister R.B Bennett and MP Agnes Macphail, Ryan was paroled in 1935. After his release he hosted a radio show denouncing crime and advocating prison reform. In 1936, he was killed outside a liquor store in Sarnia, Ont., after a botched armed robbery attempt.

4. Tim Buck: As the general secretary of the Communist Party of Canada, he was convicted of “Communist agitation” in 1931 and lived in the Kingston Penitentiary from 1932-34. Buck was involved in the violent riot in 1932 that lasted six days. During the chaos, at least five bullets were fired into his cell. Later, the government admitted that the shots were a deliberate attempt to “frighten” Buck.

5. Edwin Boyd: By the time of his incarceration in the 1950s, Boyd was a celebrity. The leader of his own bank robbing crew, the Torontonian had achieved folk-hero status after several well-executed bank heists and two successful breakouts of the Don Jail. He spent a decade in the Kingston prison. In 2011, Canadian actor Scott Speedman stared as Boyd in the movie Citizen Gangster based on his life.

6. Roger Caron: A career criminal and prison escape artist, Caron wrote several books describing his experiences in prison. Go-Boy! Memories of a Life Behind Bars won him the 1978 Governor General’s Literary Award for non-fiction.

7. Wayne Clifford Boden: Known as the “Vampire Rapist” because he bit the breasts of his victims, Boden was sentenced to three life sentences for the rape and murder of three women in Montreal and a high school teacher in Calgary. For the first time in North American history, the Crown used forensic odontological evidence to convict him. Boden began his sentence in 1972 and died of skin cancer in 2006.

8. Clifford Olson: Convicted of killing 11 children, Olson spent 10 years—from 1982 to 1992—in the pen, which he called a “rat hole.” He was often in trouble. In 1990, he was charged with possessing eight grams of hashish while in isolation. Two years later, he was caught hiding a handcuff key in his rectum and had his telephone privileges cut due to phone “abuse.” After a broom handle was found in his cell, he was moved to a prison in Saskatchewan. Olson died from cancer in 2011 at the age of 71.

9. Paul Bernardo: Since his conviction in 1995 for the murders of teenagers Leslie Mahaffy and Kristen French, Bernardo has been in segregation, locked in an eight-foot-by-four-foot cell for 23 hours a day for his own safety. Shortly after his imprisonment, he confessed to a series of sexual assaults that terrorized the Toronto suburb of Scarborough.

10. Russell Williams: In 2010, the former air force commander of CFB Trenton pleaded guilty to 88 criminal offences, including the murders of Corp. Marie-France Comeau and Jessica Lloyd. He was given an automatic sentence of life in prison with no possibility of parole for 25 years.

Sources: The Trials of James McDermott and Grace Marks, (1843); Dictionary of Canadian Biography; Canadian Encyclopedia; Maclean’s; New York Times; CBC; Owen Sound Sun Times; Kingston Whig Standard; The Worker; Toronto Sun

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