Refresh Canadiana: The Unbelievable Tale Of The Flying Bandit

Less than a week before Christmas in 1957, a man walked into a TD bank in Toronto and asked to see his friend, the bank manager. Once face-to-face with the manager, who didn't recognize him, he pulled out a gun and made his demands. The manager would write him a check, and then they would, together, go cash the check at a teller in the same bank. Ken Leishman, the man with the gun, walked out with $10,000 cash.

The second time Ken tried this, at a CIBC bank branch nearby, he failed. Ken was sentenced to twelve years in prison. What the authorities didn’t know, was that Fleishman only used this time to plan the largest gold heist in the history of Canada. When he was paroled after just three years of incarceration, Ken had his plan ready.

In the time preceding his incarceration, Ken had watched planes take off and land at Winnipeg International Airport. He owned a plane himself, which he had used to make extra cash in exchange for transporting passengers around rural areas of Manitoba. He was a flying enthusiast, and could always be found in and around planes and airports. He loved watching the activity buzz around the Winnipeg International Airport and the more he did this, the more he noticed. The transportation of gold bullion began to stand out to him and he would memorize the times when bullion would arrive at the airport from Red Lake to be flown to Ottawa.

The charismatic Ken would begin looking for partners in crime. This was never difficult for him, as he was described as a kind, easy going gentleman. People were drawn to his style and personality. He had no trouble drawing people into his schemes and in no time, he had four men signed up for the job.

On March 1st, 1966, with Air Canada uniforms handmade by Leishman himself, two of his hired guys stole an Air Canada truck and Air Canada waybills and headed to the airport. The men talked the attendants watching a gold bullion shipment into loading the gold onto their stolen Air Canada truck, and just as easy as that, they drove off with $385,000 worth of gold bullion.

The gold thieves drove the gold to one of their accomplice's homes and hid it in the freezer, on the way abandoning the stolen Air Canada truck for Leishman’s car. Unfortunately, for Leishman and crew, they weren’t thorough enough in cleaning the truck, because police recovered a fingerprint not too soon after. By March 20th, Leishman was charged with conspiracy and robbery. He made headlines around the world as, “The Flying Bandit”.

Fortunately, for our own, selfish entertainment value, the story doesn’t end there. No, Leishman didn’t like the idea of going back to prison and before he stood trial for his charges in the gold bullion heist, he sat in his cell and planned a prison break. Along with ten other men, Leishman fled the prison in September, 1966. He found a Chevy on the grounds, which he stole and used as his getaway car. He drove to an airport, where he quickly stole a plane and flew to Gary, Indiana of all places. He was accompanied by men awaiting to be tried for violent crimes. When the Manitoba RCMP finally caught up with Leishman’s gang of misfits in Gary, a standoff ensued before the men were captured and brought back to the Great White North. Police thought they could rest easy with Leishman finally locked up at the Vaughn Street jail.

They thought wrong. In October, 1966, Leishman freed himself from lock up once more by hopping the fence. It didn’t last long though. Four hours later, he was back in police custody, this time for good. He was sentenced to fourteen years in prison.

Soon after he was released by the parole board, in the late 70s, Ken Leishman is thought to have lost his life while attempting to perform a good deed. During an emergency medical evacuation flight, his plane disappeared, and the legend that was The Flying Bandit, was finally declared officially dead in 1980.

Do you know of any strange or interesting tales from Canadian history? Let us know in the comments!