One of Manitoba’s most notorious criminals wasn’t infamous for the usual reasons. He wasn’t a stalker, a murderer, or at all prone to violence. No, he was a thief. A thief, with a small plane, and big plans.
Kenneth Leishman was born on a farm in Holland, Manitoba on June 20th, 1931. When he was young, his parents divorced, leaving his mother single with young children to care for. She gained employment as a live-in household caretaker, and thought she was doing the right thing by her children.
However, young Ken did not get along with his mother’s employer. She was left with two choices, leave, or send Ken away. It was an impossible decision, but, ultimately, Ken’s mother sent him away so that she could remain employed, and care for her other children.
Ken bounced around from foster home to foster home, none any better than the others. Ken suffered abuse at the hands of these homes, and, when he was 16, decided he wanted to try to reconcile with his father, dropping out of school in favour of working rather than learning. But that didn’t mean Ken didn’t harbour sharp wit, and vast intelligence.
Ken moved to Winnipeg, where he lived with his father, and his second wife. He worked part-time with his father at an elevator repair company. Here, Ken gained vast skills, knowledge, and even met his wife. He married Elva Shields when he was 17.
While gaining access to a number of buildings due to his job, Ken started thinking. And plotting. He was living in a new apartment with his wife, and it needed to be furnished.
Ken schemed. He would pick out the items he wanted from the building he was in, and then return later, posing as an employee of that building, call a transport company, and have his hand-pickings delivered to the apartment he shared with his wife. It didn’t take long for him to be caught, and he spent a portion of his honeymoon in prison.
When he was released, he and his family moved back to the southern Manitoba farmlands, where Ken began working as a travelling mechanic in 1951 for Machine Industries. Ken travelled a lot, repairing straw cutters, and other farm equipment.
Early in 1952, due to the success of his career, Ken bought himself his pride and joy – an Aeronca aircraft. He used it to expand his business, and fly out to farms that required his services further out. He also cashed in on additional income by providing short rides in his plane.
When Machine Industries closed down, Ken found work with Queen Anne Cookware. He worked with them until 1957. The company went bankrupt, and Ken needed another plan to support his growing family.
On December 17th, 1957, Ken took his small aircraft, and flew from Winnipeg to Toronto. Once he’d landed, he headed toward a TD Bank on the corner of Yonge and Albert. Once he arrived, he put a smile on his face, and every bit the snazzily-dressed, good-looking, friendly man that he was.
He arranged to meet the bank manager, stating that he wanted to discuss a business loan. Once he gained entry into the manager’s office, he produced a gun, and, with a smile on his face, demanded a cheque for $10,000. All the while, he talked to the man, asked him questions about his friends, and family. By all means, Ken was being friendly and charming.
Once he had the cheque, and the information he wanted, in hand, Ken coerced the manager into taking him to a bank teller. Once in front of the teller with the manager, Ken demanded that the cheque be cashed. He used the information he’d learned to earn the teller’s trust, showing her that he and the bank manager were good friends.
Once Ken had the cash in hand, he led the bank manager out of bank, inviting him out for a drink. Once Ken led him to his getaway car, he let the manager go. He’d never intended on hurting anyone. He just wanted the money to support his family.
On March 16th, 1958, Ken attempted the same ploy again, his confidence having been bolstered by his success back in December.
This time, Ken wanted to rob a CIBC bank on the corner of Yonge and Bloor, in Toronto. He tried the same gambit – asking about a business loan, being shown into the manager’s office, and then pulling out a gun. The manager, however, had other ideas. He fought back.
Ken knew the jig was up, and attempted to flee the bank. As he was escaping, he was tripped by, and then tackled by a teller. He’d barely managed to get a block away from the bank.
Ken was arrested. He plead guilty to charges against him, and was sentenced to serve 12 years in Stony Mountain Penitentiary. The warden described him as “a model prisoner”.
On December 21st, 1961, Ken was paroled, and was once again faced with the arduous task of supporting his wife, and now seven children. Though one of the conditions of his release was that he couldn’t leave the province of Manitoba, Ken made it work. He worked as a door-to-door salesman. He had every intention of staying on the straight and narrow. But his family needed him, and his meagre income just wasn’t enough.
While he’d been in prison, Ken had taken some time to think. He knew the ins and outs of the Winnipeg International Airport, and he knew the basic schedule of certain shipments and deliveries. And so, in his free time, now that he’d been released, Ken would stop, and he would watch the comings and goings of the airport.
Ken knew that a TransAir flight from Red Lake would fly into Winnipeg with gold bullion, where it would be transfered to Air Canada, and flown to the mint in Ottawa. It was risky, and dangerous, and incredibly ambitious. Ken would need help.
Ken recruited four people he trusted to help him with his heist.
The first was Harry Backlin, a friend, and lawyer, from Winnipeg who provided financial backing for the heist. After that, Ken approached John Berry, and Richard Grenkow. They would be necessary for getting the gold. Ken was a familiar face around the airport, and to police. He’d never be able to gain entry. Richard’s brother, Paul, was also recruited. His job was to go to Red Lake, pose as a salesman of sorts, and alert them when the shipment was ready to leave.
Ken was also prepared with props for John and Richard. He purchased a set of winter coveralls, and stenciled the Air Canada logo on them. He also pinched some Air Canada waybills by biding his time, and waiting until the desk at the airport was unmanned, and then taking them.
March 1st, 1966 was go time.
Paul called from Red Lake, and alerted the team that the gold was being flown into Winnipeg. Richard and John donned the faux Air Canada coveralls, and then stole an Air Canada truck in order to drive onto the tarmac, and meet the TrainsAir plane.
Then, they explained that there had been a sudden change in regular procedure. Rather than wait for the usual Air Canada flight, they’d chartered a flight that was leaving immediately. No one seemed suspicious. The two men looked the part, had the truck, and had the waybills.
The gold was loaded off of the TransAir flight, and onto the stolen truck. The pair drove off, and met up with Ken where the gold was moved from the truck, to his car, all undetected. From there, Ken took the gold to Harry Backlin’s home, where he stashed it in the freezer while Harry and his family were away on vacation.
The group had successfully heisted $385,000 worth of gold.
The gold was intended to stay overnight, and then picked up in the morning to be moved to a farm in Treherne, Manitoba, which belonged to Ken’s uncle. However, Ken was stopped from retrieving the gold by a sudden snowstorm.
Harry wanted as much distance from the heist as possible, and insisted that the gold needed to be moved. Most of it ended up buried in his backyard.
Of course, the robbery was soon discovered, and the police were alerted. They found the stolen Air Canada truck, and managed to pull fingerprints off of it. It really didn’t take them long to peg Ken Leishman as a suspect. It fit his M.O – no violence, in and out quickly, friendliness, and deception.
Police investigated Ken, and his known associates, and soon found the gold buried in Harry’s yard.
On March 20th, 1966, Ken Leishman was arrested and charged with conspiracy and robbery.
As he awaited trial, Ken, assisted by accomplices, escaped the Headingly Jail in September of 1966. From there, he made his way to Steinbach, Manitoba, where he stole and aircraft and fled. The papers began calling him The Flying Bandit, and the Gentleman Bandit, for his calm, charming, thieving demeanour.
Ken took three of the ten accomplices who broke out of prison with him when he stole the aircraft. They managed to fly to Gary, Indiana.
However, they were recognized in town by a local barman, and police soon surrounded them. After a short standoff, Ken Leishman was once again arrested, and brought back to Manitoba. When he was brought off the transport plane, a crowd cheered. He smiled at the crowd, and the cameras.
Once again, Ken was awaiting trial when ambition took him. He managed, somehow, to open a foolproof locked gate. He overpowered three guards, and climbed the fence of the Vaughn Street Jail, and ran to freedom. He was caught in a phone booth a few hours later. He didn’t escape this time, pleading guilty, and serving his jail sentence.
In 1974, Ken was released from prison. He moved to Red Lake, Ontario, in 1977 where he managed Tomahawk Airlines, flying planes, chartering flights, and offering his skills as an air ambulance. He was invested in the community, and the community embraced him. He even became chairman of the Chamber of Commerce.
In 1979, Ken Leishman took on a medivac mission. While in flight, his plan disappeared in the wilds of Northern Ontario. A year later, the wreckage was spotted. The bodies of the patient, and medical assistant were found. However, Ken’s was not.
An official report and inquest theorized that Ken’s body had, perhaps, been taken by wild animals, like wolves.
On December 16th, 1980, The Flying Gentleman Bandit was officially declared dead.
But. Was he?
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Sources:
Canada history: Mar. 1, 1966: the Great Winnipeg Gold Heist – Marc Montgomery – Radio Canada International
Refresh Canadiana: The Unbelievable Tale of the Flying Bandit – The Refresher
Kenneth Leishman – The Flying Bandit – Christian Cassidy – This Was Manitoba
Ken Leishman Wikipedia page