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7 Most Famous Canadian Prisoners Who Have Escaped from Prison

7 Most Famous Canadian Prisoners Who Have Escaped from Prison

Ever think that highly-organized prison escapes were only stories you see on movies? Well think again. Canada is home to some of the most intriguing felony escapes in North America. Follow along as we name some of the most infamous jailbreaks in Canadian history.

#1 “Dear Mr. Prime Minister, Thanks For The Skates!”
Famous, robber and drug smuggler, Lucien Rivard escaped a penitentiary in Montreal with the help of another inmate. The two inmates executed their plan by offering to water the prison ice rink and then using the hose as a rope to climb over the prison wall. Not only was Rivard successful, but he even took the time to mail Prime Minister Pearson saying “Life is short, you know. I don’t intend to be in jail for the rest of my life.” Talk about an exit story.

Rivard’s escape was the talk-of-the-town for many months at the time. It inspired the song “A Government Inquiry” by the group “The Brothers-in-Law” in their album “Oh, Oh Canada.” Comedian, Rich Little, did a parody on Prime Minister Lester Pearson while singing “Old Man Rivard.” As if there wasn’t enough proof that Rivard was the most news-worthy and beloved felon of all time, The Canadian Press voted him the Canadian Newsmaker of the Year for 1965—which was the fist time a convicted felon had received the title. Rivard’s cunning escape and the aftermath following his schemes is something made in the movies.

#2 “The Prison Guard With The $50,000 Promise”
Tahvili is the only criminal in the list who escaped with the help of someone on the “inside.” Prison guard Edwin Ticne helped Tahvili escape in exchange for a $50,000 payout. Video cameras caught Ticne leading Tahvili through a series of locked doors within the prison while Tahvili was dressed in a janitor’s uniform. It was reported that Tahvili was the “kingpin” of an Iranian-Canadian organized crime family. He was convicted of kidnapping and sexually assaulting a man and is also wanted in the U.S. for telemarketing fraud, allegedly stealing $3 million from elderly American citizens. The guard was later sentenced to three years in prison in 2008. The most famous part of this escape story is that Tahvili is still on the run today following his escape from the maximum security jail in BC and is currently on the FBI’s Most Wanted list.

#3 “One Hacksaw Blade & One Wooden Leg”
Edwin Alonzo Boyd of the Body gang (whose name was given to them by Toronto newspapers) was convicted for six bank robberies and managed to escape his sentence. In prison, he befriended two other bank robbers, Lenny Jackson and Steve Suchan with whom he was able to escape. The three men were successful in using hacksaw blades to saw the prison bars the proceeded to use bedsheets to climb down to the ground. They managed to smuggle the blades through “Tough Lenny” Jackson’s wooden leg. After their escape, the men went on a robbing spree and killed a police officer while avoiding capture. More robberies followed their escape, including the largest haul in Canadian history (expected to be executed by Boyd). When they were finally captured a second time, they were able to make a shocking second escape with yet another hacksaw, this time with the help of a fourth gang member.  Eventually, however, these members were captured and hung.

#4 “When a Dummy Uses a Dummy”
Tyrone “Ty” William Conn had robbed his first bank when he was 16 years old. Two weeks after his 1999 escape, police tracked him to a basement apartment in Toronto. He managed to escape prison two more times before taking part in one of the most famous prison escapes in Canadian history. He was sentenced to serve at Kingston Penitentiary in 1998 and escaped from there just a mere year later.

Conn was able to get over the 10-metre perimeter fence of the institution at night by using constructing a ladder and grappling hook in the prison shop. hand-made ladder and grappling hook he constructed in the prison shop. The cherry on top of Conn’s escape was the fact that he created a dummy to put in his bunk by stuffing clothes with paper. His escape was not discovered until the next morning when they found the surprise laying in Conn’s bed. Although there had been at least 26 escape attempts since 1836 at Kingston Penitentiary, Conn was the first to succeed since 1958. Two weeks later, surrounded by police in Toronto, Conn committed suicide while speaking on the phone to CBC producer, Theresa Burke

#5 “Two Minute Bank Robberies & A Lifetime To Brag”
It was reported that Lionel Wright, Paddy Mitchel and Stephen Reid stole $15 million dollars from banks in the US and Canada between 1974 and 1980. The FBI called them the “Stopwatch Gang” because each bank heist lasted less than two minutes. Their escapes from prison were said to be as well executed as their robberies. Mitchell escaped through an air conditioning vent at Arizona State Prison in 1986. His departure was said to be movie-esque as it was so well-planned and went on to becoming a famous story. Mitchell, however, was later recaptured in 1994. At different times, members of the “Stopwatch” escaped from Millhaven and Joyceville penitentiaries in Ontario. They fled to the U.S. in 1979 and were captured while living a life of paradise in Sedona, Ariz. The details of their escapes were of so much interest to the general public that a documentary was made in 2013 based on their lives called “The Stopwatch Gang.”

#6 “The Doctor’s Orders”
Infamous murderer, Allan Legree, escaped prison in 1989 after being sent to a Moncton hospital in order to be treated for an infection. The felon used a strip of metal to pick his handcuffs and leg shackles then made a run for it. Along the way he kidnapped a woman and stole her car to further his escape. He then killed four people in the area of Miramichi , N.B., before he was thankfully captured once again, seven months later

#7 “Fire? Stop Drop & Roll Out of Prison”
In 1923 convicted felon, Norman “Red” Ryan successfully carried out an escape from prison along with a number of fellow inmates. Red executed his escape plan by setting a nearby shed on fire to distract the guards while he and his gang used a ladder to climb over the prison wall. The gang then stole a stole a car from a neighbouring property and left the city to never be from again.

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