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Ken Leishman was the unlikeliest of folk heroes. Despite numerous trips to, and escapes from, prison in the 1950s and ’60s, the "Flying Bandit" wasn’t considered a public enemy. Instead, he became a media celebrity and a respected community leader.

William Kenneth Leishman was born on a farm near Holland, Man., July 20, 1931, the middle child of Norman and Irene Leishman.

The March 1966 gold heist from the Winnipeg International Airport made headlines around the world.</p></p>

The March 1966 gold heist from the Winnipeg International Airport made headlines around the world.

Throughout the Depression years, the family jumped from community to community in search of work.

In 1938, Ken’s parents separated, leaving Irene to raise their three children. She found work in a rural community as a live-in domestic for a widowed farmer who did not take kindly to young Ken.

She told the Free Press’s Gordon Sinclair in 1966, "He used to beat Kenny with a stick of stove wood. He pounced on him for everything."

Mrs. Leishman was given an ultimatum by her employer: leave her job (and home) or get rid of Ken.

As a single mother in the midst of Depression-ravaged rural Manitoba, she felt she had no option and the seven-year-old spent the next few years bouncing from relative to relative, then foster home to foster home, never staying more than a few months at any one place.

A feature of Leishman’s teenage years was bad luck that surfaced whenever he seemed to be getting his life on track. From the age of 14 to 16, he lived on his grandparents’ farm, a relatively tranquil period in his upbringing that was marred by accidents, including being kicked in the head by a horse, (something his mother blamed for some of his later behaviour.)

Leishman then moved to Winnipeg to reunite with his father. After a few months, he was off to Kenora, Ont., to work at a summer resort, an opportunity that was thwarted by a broken ankle soon after his arrival. Later that year, a chance to work on a ship in the Great Lakes also ended abruptly when his appendix burst.

In 1950, at the age of 18, Leishman married 17-year-old Elva Shields and the two settled in Winnipeg. The marriage got off to a rocky start when he was soon arrested for stealing some of the items used to furnish their first home and spent four months in jail.

University of Manitoba Archives / Winnipeg Tribune Collection</p><p>Ken Leishman’s mugshot taken after he was charged in connection with the March 1966 gold heist.</p></p>

University of Manitoba Archives / Winnipeg Tribune Collection

Ken Leishman’s mugshot taken after he was charged in connection with the March 1966 gold heist.

Throughout the remainder of the decade, the couple, who would have seven children, lived at a different address every year or two as Leishman bounced from job to job as a salesman or repairman. He had a pilot’s licence and owned his own plane, so some of those jobs required flying into rural communities.

It turns out one of those fly-in jobs was one he kept hidden from his family, that of a bank robber.

Leishman’s first known bank robbery took place Dec. 17, 1957. He flew into Toronto on a commercial flight, rented a car and put himself up in a posh hotel. The next day, Leishman went to a TD Bank branch on Yonge Street and asked to meet with the bank manager, claiming to be a businessman from Buffalo, N.Y., looking to open an account.

Once inside the manager’s office, Leishman calmly produced a gun from his briefcase and told the manager to write a cashier’s cheque for $10,000.

The two men waited their turn in the teller’s queue and Leishman made small talk about the manager’s family to pass the time. Once the money was handed over by the unsuspecting teller, Leishman calmly walked out of the bank and disappeared onto Yonge Street. That night, he returned to Winnipeg and a family that assumed he had been away on one of his legitimate work trips.

A Canadian Press story called the Toronto holdup "one of the most daring robberies on record." The bandit was described in the media as well-spoken, nattily dressed and gentlemanly.

Leishman returned to Toronto on March 17, 1959, looking to score $25,000 from a Bank of Commerce at Bloor and Yonge streets.

This time, Leishman got an unexpected reaction when he produced his gun. The manager became angry and exclaimed "You won’t get away with this!" As he made for his office door to tell his staff to sound the alarm, Leishman rushed past him and out of the building.

Pursued by two bank employees as he sprinted down Yonge Street, Leishman tripped over someone and fell to the sidewalk. The employees held him until a nearby police officer arrested him.

Leishman pleaded guilty to the two robberies and, in April 1958, was sentenced to 12 years in prison. At his sentencing hearing he told the judge, "I had no reason for doing it and many reasons for not doing it. I regret the shame it has brought on my family and which it will continue to bring them."

He told Toronto police he stole the money to finance a fishing camp that he and his father wanted to build in northern Manitoba, but he likely had more pressing debt issues.

Leishman, top, being escorted back from Gary, Indiana where he was captured after his escape from Headingly Jail in September 1966.

UNIVERSITY OF MANITOBA ARCHIVES / WINNIPEG TRIBUNE COLLECTION

Leishman, top, being escorted back from Gary, Indiana where he was captured after his escape from Headingly Jail in September 1966.

Though he made a decent living, Leishman liked the finer things in life. He drove a Cadillac and dressed in designer clothing. In his private plane he went off to watch Grey Cup games and the year before his arrest, flew the family to Texas for vacation. It was all too much while juggling mortgage payments and providing for his then five children.

Leishman was allowed to serve his sentence at Stony Mountain Institution and was released in less than four years. The warden noted he was courteous, well behaved, had upgraded his high school courses and learned a trade. He was a model prisoner.

After his release, Leishman appeared to be get his life together. By 1963, the family owned a home on Mark Pearce Avenue in North Kildonan and he began a long-term job as a fly-in salesman for World Wide Distributors, sellers of stainless-steel cookware and kitchen appliances.

What people didn’t know was during his time in prison Leishman began planning a heist that would make his Toronto jobs pale in comparison.

As a pilot, Leishman knew that regular flights delivered gold bullion produced at Red Lake, Ont., to the Winnipeg International Airport. From there, it was transferred to an Air Canada plane destined for Ottawa, where the Royal Canadian Mint was located at the time.

Leishman assembled a group of four accomplices. The supplies they needed consisted of white coveralls on which they stencilled the Air Canada logo, a blank waybill form doctored to look like a legitimate cargo transfer, and an Air Canada van, which they stole.

On March 1, 1966, two of the men drove the van through a back gate of the airport grounds and onto the tarmac to meet the Red Lake plane. The cargo was transferred to the van, the paperwork was signed and they drove away with 12 bars of gold valued at $363,000. It remains Canada’s largest gold heist.

Though the theft itself went without a hitch, as usual, luck was not on Leishman’s side.

The following day, a snowstorm began that would turn into one of the worst blizzards in Winnipeg’s history. It ground traffic to a halt and covered the city in a deep blanket of snow, which made properly disposing of the stolen van and burying the stolen gold impossible.

Phase two of Leishman’s scheme involved selling the gold on the black market in Hong Kong. The man chosen to go there with one of the bars to make the deal, a local lawyer, had his passport application rejected due to insufficient paperwork. It was then decided Leishman would go in his place.

Leishman didn’t know police were already on the trail by the time he boarded the plane in Winnipeg. While waiting for his connecting flight in Vancouver, he was arrested by RCMP officers. (The gold bar he was travelling with was never discovered.)

The blizzard of 1966 began the day after Leishman's gold heist preventing the gang from properly disposing of the stolen van and burying the loot.

UNIVERSITY OF MANITOBA ARCHIVES / WINNIPEG TRIBUNE COLLECTION

The blizzard of 1966 began the day after Leishman's gold heist preventing the gang from properly disposing of the stolen van and burying the loot.

Leishman was returned to Winnipeg and charged with parole violation for leaving the province. This gave police time to build their case against him for the robbery.

Thanks to his reputation as a bank robber, Leishman was considered a prime suspect by Winnipeg police as soon as the gold theft was reported. They also discovered his name when they traced airline tickets purchased from Winnipeg to Hong Kong, knowing it would be one of the few places in the world one could go to offload that much gold.

The nail in the coffin, though, was that one of the accomplices was tracked down after police found his fingerprint in the stolen van. He confessed. One by one, the other accomplices were questioned and charged.

On Sept., 1, 1966, while awaiting trial for parole violation, robbery and conspiracy at Headingley Jail, Leishman masterminded a jail break involving 10 prisoners. The group overpowered a guard, grabbed his keys, broke into the office to steal weapons and fled the institution.

Leishman and three other prisoners, a murderer, a rapist and someone awaiting transfer to Selkirk Mental Hospital, stole a car and made for the border.

Listening to the news as they drove, it was clear they would not make it to their destination by car. In what was described in one newspaper story as "the largest manhunt in Manitoba’s history," every RCMP officer in the province was called in to set up roadblocks at the entrances to major communities. Airports and border crossings were also put on notice.

The escapees stopped in Steinbach where Leishman stole a plane and flew them to the U.S. They were discovered the following day in Gary, Ind., after a bartender recognized their faces from local news coverage. After a brief standoff with police, they were arrested and returned to Winnipeg.

By this time, Leishman was an instantly recognizable celebrity and justice officials thought it was best to keep him segregated from other inmates while he awaited trial. He was held at the Vaughan Street Jail in a small, empty wing.

Because there were no other prisoners, Leishman at times had access to the corridor outside his cell to allow him to exercise. On the evening of Oct. 31, 1966, he decided to use that to his advantage and attempted another jail break.

At around 7 p.m., he picked the lock at the end of the corridor and overpowered three guards, tying one up with a bedsheet and threatening two others with a steel pipe. He made it out of the building and set off another huge manhunt.

This time, though, there was a less thrilling ending to the escape. Leishman was arrested without incident nearly four hours later by West Kildonan police at a phone booth at Main Street and Jefferson Avenue.

The picking of the industry standard prison lock from the inside baffled officials and the director of the jail invited Leishman to come back and re-enact how he did it. He complied, showing them all he used was a long strip of cloth from a bedsheet and a piece of wire. With them, he was able to remove a horseshoe-shaped pin from the locking mechanism and the lock was free.

Leishman pleaded guilty to a list of nine charges and on Nov. 1, 1966 was sentenced to seven years. This was on top of the eight years he that he now had to resume serving for his Toronto robberies because of the parole violation.

Denied parole in 1974, Leishman requested an official review of the length of his sentence, which was a complicated web of timelines, some running concurrently and some consecutively.

The parole board agreed, and during the review a number of mathematical errors were found. When calculated as laid out in official documents, it turned out Ken Leishman had already served his time and the board had no option but to release him. (The discovery prompted a review of hundreds of other cases in Manitoba’s justice system.)

After prison, Leishman was finally able to bask in his celebrity status with numerous media interviews, including a national TV appearance on Peter Gzowksi’s 90 Minutes Live during which he charmed the host and the studio audience.

Hollywood also came calling in the form of actor Darren McGavin, who bought the rights to Leishman’s life story. The two men spent time together in California and McGavin came to Canada to scout out filming locations. For reasons unknown, the film project never proceeded.

In 1977, the Leishman family relocated to Red Lake, Ont., where Elva and Ken opened a clothing and gift shop. The couple were so popular that Ken was elected head of the town’s chamber of commerce the following year.

While he may have given up his life of crime, Leishman did not give up his love of flying.

On Dec., 14, 1979, he was piloting a medi-vac flight from Red Lake to Thunder Bay with a patient and medical escort aboard. The plane never arrived.

Despite an extensive search and rescue operation the plane’s wreckage was not discovered until the following spring. The bodies of the two passengers were identified but all that could be found of Leishman were scraps of clothing and a chewed-up wallet.

On Dec. 16, 1980, Ken Leishman was declared legally dead at the age of 48. He left behind his wife of 30 years, seven children, and quite a legend as Canada’s Flying Bandit.

Christian Cassidy writes about local history on his blog, West End Dumplings.

Christian Cassidy

Christian Cassidy
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Christian Cassidy believes that every building has a great story - or ten - to tell.

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