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A fire which broke out on May 15, 1934, in the change room at Kingston Penitentiary and caused dense columns of smoke to spread across the city.


The first prisoner was Mathew Tavender, who was sentenced to three years for grand larceny. John Hamilton was the second inmate, also sentenced to three years for a felony. Mr. Tavender and Mr. Hamilton were both whipped on Aug. 30, 1835, implying they had tried to make contact, which was against prison rules. The third inmate, Edward Middlehurst, was sentenced to five years for grand larceny but he was released a year later after he became sick. Historians suggest he may have received a pardon, a common way to deal with sick prisoners to avoid spreading illness or paying for a gravedigger in the case of death. John O'Rourke, inmate No. 4, was beaten with a rawhide whip two weeks after his arrival. The fifth inmate, John Dayas, was appointed as the cook on his second day at the prison. Joseph Bonsette was the sixth inmate, shuffling through jobs until he was made a shoemaker. He was released in 1840.


By the fall of 1835, there were 52 male inmates and three women. Susan Turner, Hannah Downes, and Hannah Baglen were the prison's first female inmates, sentenced on Aug. 28, 1835 for grand larceny. Women were housed in the prison's north wing before the separate Prison for Women opened in 1934. The men were held in the south wing and immediately put to work constructing other cell blocks and a wall around the jail.


On April 25, 1904, a Kingston prison guard foiled an escape plot after a bogus nun smuggled money to the men convicted for an attempt to blow up the Welland Canal. They planned to bribe a guard and flee. Authorities alleged the woman accompanied a legitimate nun on a spiritual meeting with the inmates. A guard said he saw one of the nuns slip a package to one of the three convicts, who was found with money hidden in the lining of his coat. The package supposedly held $1,000, though most of it was not recovered.


Some of the prison's most infamous prisoners include Steven Truscott, who was sentenced to death for the murder of Lynne Harper but later acquitted; child killer Clifford Olson; killer Paul Bernardo; and Ty Conn, who escaped from the prison in 1999.


When the notorious gangster Norman 'Red' Ryan escaped from Kingston Penitentiary with four other men on Sept. 10, 1923, The Globe made it front-page news for weeks. The convicts set fire to a barn full of hay and the smoke blocked the prison guards' view as the five men used a makeshift ladder to scale the prison's 24-foot wall. Mr. Ryan, the last to climb the wall, hit Chief Keeper Matt Walsh with a pitchfork before fleeing in an old Chevrolet with the other escaped bandits. Ernest Hemingway reported on the story for the Toronto Star.


On April 14, 1971, a riot broke out in the prison's gymnasium. Six guards were taken hostage, their keys seized and the whole prison population was released. Two inmates were killed before the riot ended. Prison authorities negotiated by telephone with a committee of inmates who demanded to speak with a Kingston radio journalist, Gerry Retzer, to inform the public about their grievances, including total isolation from society that the prisoners felt was failing to help them re-integrate upon release. The army was called in to helped restore control.