Red Ryan’s Ultimate Prison Escape

The devil’s greatest trick was convincing the world he didn’t exist.

Norman ‘Red’ Ryan was born 1895 in Ontario to a Catholic family. As soon as he could walk he began getting into trouble stealing chickens and bicycles. These tendencies only escalated with age. He gravitated towards bank robberies where he usually worked alone. His strategy was to walk in with a pistol, vault over the counter and help himself to the cash. Often within a few minutes he had vaulted back over the counter and sauntered off with thousands of dollars. This was no mean feat and required determination and athleticism as typically bank counters were quite high.

Red Ryan was sent to Kingston Penitentiary several times over his lifetime. He was first sentenced for bank robbery aged nineteen. After his release, Red Ryan was involved in multiple robberies and shootings until he was re-apprehended by police and sent back to Kingston. This time, he was expected to serve a long sentence but was released into the army in order to serve in World War I.

After World War I he returned to Canada and was pardoned for his crimes as a result of the war. However, he quickly began getting into trouble again. In 1922, he was once again sent back to Kingston Penitentiary, and sentenced to twenty-five years for armed robbery and shooting with intent to maim.

Red Ryan’s mugshot
[Credit Random House]

During this sentence, he acquired a carpentry job within the prison, and built a ladder tall enough to climb over the prison walls. Red Ryan started a fire to distract the guards and, along with four other inmates, escaped. The escape did not go completely unnoticed however, and the guards were able to put up some resistance. Red Ryan went up the ladder last, holding off the guards to allow his companions to escape. At the start of his career, Ernest Hemmingway was writing for the Toronto Star, and covered the escape in an article which portrayed Red Ryan in a heroic light. It was the first of many similar articles to come. Before long, the newspapers were raving about him and his crimes and he went on to become a minor celebrity.

After his escape, Red Ryan spent a few years in America, continuing to rob banks and, was living the high-life. He was ultimately caught, and extradited back to Canada where he was sentenced to life in Kingston Penitentiary. Due to the severity of his crimes and the length of his sentence, he was sent straight into solitary confinement for the first months of his sentence.

The only visitor permitted to visit Red Ryan was the Chaplin, Father Wilfred Kingsley. Father Kingsley was a firm believer in reforming, rather than punishing prisoners for their whole sentence. In Red Ryan he saw an opportunity to publicise his cause, and in Father Kingsley Red Ryan saw an opportunity to keep his name in the public mind, and thus he reignited his acquaintance with Catholicism.

For several years Red Ryan was the model prisoner. His good behaviour earned him a job in the prison hospital, as well as private living quarters. He even wrote a book called The Futility of Crime which declared his life to have been a series of big mistakes from which he had reformed in favour of atonement. Throughout his prison sentence he was regularly in communication with the Toronto Star, claiming that crime doesn’t pay and that going straight was the best thing he ever did.

The people of Canada started to think that perhaps he should not be in prison any longer, as it seemed like he was a reformed man who would be better off out in the community spreading his message of staying on the right side of the law. The Toronto Star was one of Red Ryan’s main champions for release, publishing multiple interviews with people advocating for his freedom. Many powerful leaders and people of standing also believed Red Ryan should be released.

It might have gone no further than public opinion, were there not an election forthcoming. After a riot at Kingston Penitentiary (notably, Red Ryan did not partake) prison reform was one of the major subjects under scrutiny.

In 1935, Prime Minister Richard Bennett visited Red Ryan in prison. The exact nature of their conversation is not known, but the result was. Despite great opposition from the police and the parole board, in July 1935 (three months before the election), Red Ryan was given a full pardon and released from prison.

During the first week of Red Ryan’s freedom, the Toronto Star ran articles every day featuring him as the hero. He attended events as guest of honour, had photos taken with judges and members of Toronto’s high society and even hosted the Toronto Police Athletic Association Field Day. The Toronto Star gave him a permanent column to write about his life, and was given had his own radio show to mourn his wasted years of crime.

It was all a lie.

A few months after his release, Red Ryan planned the robbery of a liquor store in the small town of Sarnia. The store had one door to enter and another to exit, and locals knew that the exit door typically didn’t shut properly unless locked and so could be used to gain entry. The shop was on the first floor, so upon entering the building, customers were greeted with a flight of stairs.

The robbers entered at about ten to six and waited on the stairs for the last customers to leave before the shop closed at six. They locked the door behind them, preventing new customers from surprising them. One of the customers already in the shop was 25 cents short and looked down the stairs in hope of an acquaintance he could borrow the money from. Instead he was faced with the waiting robbers, forcing them to strike before the shop had cleared. Another customer did attempt to enter and, when he found the door locked before 6pm, decided to try the exit instead. From the stairs he heard the robbery in progress and quietly slipped back outside where he fled to a nearby taxi. The driver contacted the police over his radio and they were soon on their way.

The police arrived and entered the building through the exit. A gunfight broke out between the police and the robbers, while customers and staff hid. Police officer P.C. Jack Lewis was killed during the fight, and both Red Ryan and his accomplice Harry Checkley also died. Because the robbers were wearing masks none of the police realised who they were dealing with until they checked the bodies and found Norman ‘Red’ Ryan was not, and never had been, reformed. Instead he had pulled an incredibly elaborate prison escape.

References:  –  True North Heists  –

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