Ken Leishman, always smiling, always well-dressed, and ever-entertaining as a guest on the Peter Gzoski TV show in 1977, probably the best-iked criminal in Canadian history

Ken Leishman, always smiling, always well-dressed, and ever-entertaining as a guest on the Peter Gzoski TV show in 1977, probably the best-iked criminal in Canadian history
Photo Credit: CBC-monarch films

Canada history: Mar.1, 1966: the Great Winnipeg Gold Heist

If this was the US they would have made a blockbuster crime-thriller feature film about one of the biggest heists in Canadian history, and the dapper mastermind behind it.

Just on his other escapades alone Ken Leishman’s story would have made a great Hollywood-style film, but surely the Great Winnipeg Gold Heist would be the icing on the thrilling cake so-to-speak.

A gentleman bandit

In a strange twist, one of Canada’s most notorious criminals was actually admired by Canadians. Why not? He was astoundingly bold, was an open friendly likeable guy, he was always well-dressed, always well-spoken, and no-one was ever hurt in his crimes.

Well-dressed, well-spoken, Canada’s gentlemen bandit, a dapper and daring folk hero.

In the 1950’s and 60’s Leishman stole planes. He robbed banks across Canada. He  staged prison breaks. Then he committed one of Canada’s greatest robberies.

Born in Manitoba, Ken Leishman had had a very rough life as a child. His parents divorced when he was a child and he spent time in a variety of foster homes with abuse thrown in for good measure.

He later ended up at his grandparents farm, but was twice kicked in the head by horses, leading to who knows what exactly kind of long term brain injury of character alteration.

Later he tried his hand at a number of jobs, but bad luck followed him, and in addition to things like a broken ankle and burst appendix, he suffered another concussion while working on the railway and was in a coma for three days, all this while still a teenager.

At 18 he married, but his life of crime also began when he stole furniture for the new apartment. Arrested, he spent part of his honeymoon in jail.

Later he seemed to get his life together and after taking a couple of flying lessons, bought a plane and although he never actually bothered with the formality of getting a pilot’s licence, he became a flying farm machinery repairman. Later, he became a salesman for cutlery and cookware.

But he had a wife, and now children, a house in Winnipeg and a plane to support.

Ken Leishman, well-liked family man, here with his wife and seven children, but the mastermind of the most daring robberies and jailbreaks in Canadian history. © Telefilm Canada
Ken Leishman, well-liked family man, here with his wife and six of eventually seven children, but secretly the mastermind of the most daring robberies and jailbreaks in Canadian history. © Telefilm Canada

In addition he was a snappy dresser and loved a good life. It was too much for his acceptable but insufficient income.

In November 1957 when he was only 26 years old, the cookware company where he was a salesman closed and he would soon be in deep financial trouble.

A month later Ken Leishman legend began as he staged the first of many extremely bold robberies.

He flew the over 1500 kilometres from Winnipeg to Toronto, a daring feat in itself in a Canadian winter in a small plane.  After spending the night in a luxury hotel, he entered a bank downtown and on the pretext of a business loan got to see the manager. Behind closed doors he pulled a gun and forced the manager to write a $10,000 cheque.

He then questioned the man about his life and family, which might seem odd at, first but Leishman was smart.

Heading to the teller with the nervous manager beside him he used the information he had just been told in a friendly conversation to easily convince the teller he was a good personal friend of the manager. The teller obligingly cashed the cheque with a smile. Leishman, maintaining the ruse, had the manager accompany him to the getaway car outside, thanked him, and sped away, leaving the manager somewhat flummoxed on the sidewalk.

He drove to the airport and flew back to Winnipeg. The police were of course baffled; who was this guy? Where did he come from and go? None of their usual sources had any idea, and the style of the crime was entirely new to them.

A few months later in March 1958, he tried the same thing, but this time he was caught outside after a teller pressed the emergency button, and he tripped over a passer-by outside.

Sentenced to twelve years, he was out in three and half after being what the warden described as “a model prisoner”.

One of his conditions was that he couldn’t leave the province of Manitoba.

For the next few years, things were quiet, (as far as we know) but then on March 11, 1966 he was picked up by police in Vancouver for parole violation for having left Manitoba, and sent back to serve the rest of his sentence in prison in that province.

Boldest and biggest gold heist in Canada

But police were already desperately trying to connect him to perhaps the boldest and biggest robbery in Canadian history which had taken place a little over a week earlier.

From his experience of flying out of Winnipeg airport, Leishman knew that gold bullion from the mines in Red Lake in northwestern Ontario were flown in on small planes to the Winnipeg airport on a semi-regular basis. They would later be transferred to larger Air Canada planes for the flight to the national mint in Ottawa Ontario.

Leishman  worked out a plan.  He gathered four accomplices including a lawyer to finance the plan.  One of the gang was sent up to Red Lake airport in Ontario. That man was to advise the others when a gold flight had taken off from the little airport there for the approximately three hour flight.

On March 1st, 1966 the call came that a gold flight was on its way to Winnipeg.

Leishman, being too well known hismelf, had two others disguised with coveralls as Air Canada employees.  With fake Air Canada waybills that Leishman had snatched from an unattended counter, and an Air Canada truck they had stolen.  The two men drove out to meet the arriving plane.

They explained to the crew that there had been a change of plans and Air Canada had a chartered plane ready to go instead of waiting for the regular flight.

With an Air Canada truck, uniforms and apparently proper waybills, the boxes of gold bars were loaded onto the truck which drove away.with about $385,000 dollars worth of gold, something in the neighbourhood of $3 million in today’s value.

A bold brilliant well-executed plan, again with no one hurt.  The spectacular robbery made headlines across Canada and indeed around the world.

The plan went perfectly, but for a very simple flaw.

Police soon discovered the abandoned Air Canada truck and found fingerprints. Suspecting the well-thought out plan had to be the work of a mastermind, they suspected Leishman and began investigating all his contacts.

It didn’t take long before the found the trail.  They eventually recovered the gold buried in a backyard,  and connected Leishman to the daring robbery.

By this time, though Leishman was already something of a folk hero, as an “everyday” working man but who carried out these bold robberies without hurting anyone. His ever-present smile, friendly demeanor, and snappy dress didn’t hurt his image either.

On March 20, he was charged with conspiracy and robbery.


That’s not the end of his bold adventures though as he later organized a breakout of ten prisoners. In spite of roadblocks and a massive manhunt Leishman, with three others, stole a plane and flew to Gary Indiana in the USA. This was a reinforcement of his reputation as the “flying bandit”

Recognized from news reports by a local barman,, police surrounded them and after a brief shootout and standoff they were returned to Manitoba, where Leishman, still smiling, noticed the crowd which had come to the airport to see him and cheered him as some kind of modern Robin Hood.

Leishman (top right) in custody after being returned from Indiana
Leishman (top right) in custody after being returned from Indiana ©  U Manitoba- Tribune collection

His story is still not over. As the lone prisoner in the old  Vaughn Street jail in Winnipeg, he managed to open a supposedly foolproof locked gate, overpowered three guards and clambered over a fence to freedom.

It was short –lived as he was picked up at a phone booth a few hours later, and spent the next several years in jail.

Released in 1974, he moved to Red Lake in 1977, where as a pilot and local businessman he was well-liked and became chairman of the local Chamber of Commerce and began using his flying skills as an air ambulance.

The end..or maybe not?

In 1979 as the pilot of a medivac mission, his plane disappeared over northern Ontario. The wreckage was spotted the following year and the bodies of the patient and medical assistant were found, but not Leishman’s . This led to speculation that he had “escaped” again.

An inquest later speculated that animals, perhaps wolves, had taken the body away and eaten it. He was declared officially dead on December 16, 1980.

The gentleman thief’s story lives on however through a 2005 television documentary, written by Bob Lower and directed by Norma Bailey, entitled Ken Leishman: The Flying Bandit recounts his life and career as a criminal.

There was also a theatrical play in 2007, The Flying Bandit by Lindsay Price, a book ,The Flying Bandit by Heather Robertson) and a “non-fiction novel” based on his life, called Bandit: A Portrait of Ken Leishman by Wayne Tefs.

However, one wonders why there isn’t a Canadian feature film on one of the most colourful (and likeable) bandits in Canadian history?

Of note, about twenty years later, another Canadian robber would also take the title of “The Flying Bandit” using much the same methods and robbing dozens of banks across Canada from his home in Ontario. His name is Gilbert Galvan

TRAILER- YOUTUBE- Monarch Films documentary

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