On December 14, 1979, a light aircraft of Sabourin Lake Airways disappeared while on an air ambulance flight out of Red Lake, in the Canadian province of Ontario. Aboard were pilot Ken Leishman, nurse Janet Meekus, and patient Eva Harper, an indigenous woman who had broken her hip in a snowmobile accident. So wild and remote was the crash site that it was not discovered until the next spring. Members of the Canadian Armed Forces sent to find the wreckage successfully identified the remains of Meekus and Harper, but strangely those of the pilot were nowhere to be found. Though the Coroner would later conclude that the body had most likely been dragged away and eaten by wolves, others weren’t so sure, for Ken Leishman was no ordinary bush pilot. While outwardly this charming, generous man with an easy smile and Errol Flynn moustache appeared a model citizen and pillar of the Red Lake community, he had, in fact, a long and infamous criminal history. For nearly a decade, Ken Leishman engineered a string of brazen, headline-grabbing robberies including the single greatest gold heist in Canadian history, earning him a reputation as a Robin Hood-like folk hero and the enduring nickname of “The Flying Bandit.”

Kenneth Leishman was born on June 20, 1931in the small farming town of Holland, Manitoba, the second child of Norman and Irene Leishman. Kenneth’s childhood was a troubled one. His father was abusive and an alcoholic, resulting in his parents separating in 1938. His mother, left to raise three children alone in the depths of the Great Depression, soon found work as a live-in domestic for a local widower. Unfortunately, the situation for young Kenneth did not improve, for his new stepfather proved just as abusive as his biological one. Facing the prospect of losing her home and livelihood, Irene Leishman was forced to make the heart-wrenching decision to send her son into foster care.

Over the next few years Kenneth bounced between various foster homes before winding up in a Children’s Aid orphanage. In 1943, after Irene’s divorce from Norman Leishman was granted, she married William Brooking and invited Kenneth to live with the new family in the town of Treherne. Unfortunately, Kenneth did not get along with this stepfather either, and was sent away to live on his grandparents’ farm. Though life on the farm brought much-needed stability to Kenneth’s life, he was beset by bad luck and suffered a number of severe injuries, including being kicked in the head by a horse. This injury in particular would later be blamed for his eventual criminal behaviour.

At age 16, Kenneth dropped out of school and reconciled with his biological father, who had settled in Winnipeg with a new wife and found work with the Western Elevator and Motor Company. For four years Kenneth lived with his father, working half the year at the elevator company and the other half at a cottage country resort in Kenora, Ontario. Then, while attending a funeral in Treherne in the summer of 1947, he met 20-year-old Elva Shields. The two fell immediately in love and were married the next year. It was to prove a tumultuous honeymoon period, for it is around this time that Ken Leishman began his descent into a life of crime. Leishman’s job at the elevator company granted him free access to various office buildings, allowing him to case the properties for furniture and other products he needed to furnish his new family’s home. Once he had located the items he wanted, he would break in after hours and, posing as a company employee, call a shipping company to pick up the items and deliver them to his home. At first this scheme proved extraordinarily successful, with his thefts in February 1950 alone consisting of a radio, refrigerator, kitchen range, Chesterfield suite, dinette suite, and a bed worth the equivalent of $11,000 today. But it could not last, and in March of that year a shipping company dispatcher grew suspicious of Leishman’s late-night calls and alerted the police. Leishman was arrested, plead guilty, and was sentenced to nine months in jail, though he got out on good behaviour after only three.

Upon his release, in 1951 Leishman found work at Machine Industries, travelling around southern Manitoba repairing straw cutters and other farm machinery. He also decided to pursue his lifelong passion for aviation, taking flying lessons and buying his own aircraft in order to more easily reach the remote farms he serviced. He did not, however, bother to obtain a pilot’s license, and in 1953 received a two-year suspended sentence for flying without one.

By the mid 1950s things seemed to be going well for Leishman. He had a stable job, a large house, a Cadillac and a plane, and a thriving family of five children. In reality, however, Leishman was living well beyond his means. Machine Industries had gone bankrupt, forcing Leishman to find a job at Queen Anne Cookware where worked until November 1957 when it, too, closed its doors. Worse still, Leishman had recently invested his life savings in a failing fly-in fishing resort in northern Manitoba. Running desperately low on capital, Leishman did what any reasonable person would do and decided to rob a bank.

On the pretence of making a business trip, Leishman boarded a commercial flight to Toronto and checked into a luxury downtown hotel. He would later claim that while there was money to be had in Manitoba, much of it was tied up in land and investments; Toronto, on the other hand, was a place where cash flowed more freely. On December 17, 1957, Leishman walked into the Toronto-Dominion Bank on the corner of Yonge [“Young”] and Albert street and, posing as “Mr. Gair,” a businessman from Buffalo, New York, asked to speak to the bank manager about a business loan. On entering the office, Leishman produced a gun and forced the manager to write out a cheque for $10,000 – all while questioning him about his personal life. The details he gleaned allowed him to pose as a close friend of the manager as he walked him to a teller and had the cheque cashed. Then, on the pretence of going out for a drink, Leishman escorted the manager out of the bank before hopping in his getaway car and speeding away, leaving the manager – shaken but unharmed – on the sidewalk.

The brazen crime stunned and confounded the nation; nothing like it had ever been seen before in Canada. Polite, charming, and impeccably dressed, Leishman did not fit the profile of a typical bank robber, and the police found themselves without any leads. Buoyed by his success, Leishman returned to Toronto on March 16, 1958, this time to rob the Canadian Imperial Bank of Commerce on Yonge and Bloor Street. However, this time he was not so lucky. The bank manager refused to cooperate and a scuffle ensued, attracting the attention of a teller who proceeded to activate the alarm. Leishman fled the bank but was tripped by a bystander and tackled by bank staff, who held him until the police arrived. Leishman pleaded guilty to both robberies and was sentenced to 12 years at Manitoba’s Stony Mountain Penitentiary.

Leishman took to prison with his usual energy and charm, as his son Ron later recalled:

“He was well liked at Stony Mountain. The warden used to have him over for dinner. They had a Toastmasters club in the prison, and he was the president. He ran the hockey league. If some guy was having a problem with his wife or girlfriend, Dad would write a romantic poem he could send.”

During Kenneth’s imprisonment, Elva Leishman ran a gift shop in Winnipeg to support the family, which had by now grown to seven children. Meanwhile, Leishman’s exploits had turned him into a dashing, romantic folk hero and earned him the nicknames “The Gentleman Bandit” and“The Flying Bandit.”

Described as a “model prisoner” by the warden of Stony mountain, Leishman was released after only three and a half years, on condition that he not leave the province of Manitoba. For a while, at least, things seemed to go back to normal. Leishman got a job as a fly-in kitchenware sales representative for World Wide Distributors and purchased a new family home in a fashionable Winnipeg suburb. But then, in March 1966, Leishman was arrested for parole violation at the Vancouver airport and escorted back to Winnipeg by the Royal Canadian Mounted Police. While at first this appeared to be a minor incident, the RCMP soon became convinced that Leishman was in fact behind one of the most brazen crimes in Canadian history: the theft of 360 kilograms of gold in broad daylight from the Winnipeg International Airport.

The idea for the Great Gold Heist came to Leishman while idly watching aircraft take off and land from the airport. He noticed the arrival of regular Transair flights carrying gold from mines at Red Lake, which were then shipped by Air Canada to the Royal Canadian Mint in Ottawa. Leishman formulated a plan to steal the gold while incarcerated at Stony Mountain, and upon his release he set about assembling a team to pull it off. To finance the operation Leishman sought the help of lawyer Harry Backlin. While a law student Backlin had visited inmates at Stony Mountain and befriended Leishman. The two became fast friends and even went into business together, running a small cleaning supplies wholesale business on the side. As he was by now too well known by the police, Leishman hired two accomplices, Richard Grenkow and John Berry, to actually steal the gold. To help them infiltrate the airport, Leishman bought a pair of white winter coveralls and stencilled the Air Canada logo on them. He also obtained Air Canada freight waybills by waiting around the freight counter until the staff went to lunch and simply helping himself. Meanwhile, Richard Grenkow’s brother Paul was sent to Red Lake  to act as a lookout.

On March 1, 1966, Paul Grenkow called Leishman to report a large gold shipment had just left Red Lake, and Richard Grenkow and John Berry were dispatched to the airport to intercept it. The pair stole an Air Canada truck and made their way onto the tarmac, where the recently-arrived Transair plane was being unloaded. Posing as Air Canada employees, Grenkow and Barry explained that an earlier charter flight was waiting, and that Air Canada wanted to get the gold out sooner rather than later. As the men had the proper uniforms and documents, the ground crew bought the ruse and the shipment was duly loaded onto the truck. Grenkow and Barry then simply drove out of the airport with 360 kilograms of gold worth $385,000 – or nearly $13 million today.

Just a few kilometres outside the airport, Grenkow and Barry ditched the truck and loaded the gold into Leishman’s waiting getaway car. The trio then drove to the house of Harry Backlin. Though Backlin was away on vacation, his mother was home housesitting, and in delightfully Canadian fashion the trio explained they were delivering a load of moose meat Backlin had ordered. Backlin’s mother kindly led them into the basement, where the trio stashed the gold in a chest freezer. Leishman intended to move the gold the next day to his uncle’s farm in Treherne, but in a stroke of bad luck one of the worst blizzards on record foiled these plans. Backlin, who had by this time distanced himself from the scheme, returned from vacation and demanded the gold be removed from his basement. It was instead buried in the snow in the back yard until the weather improved sufficiently to move it.

However, the police were already hot on the conspirators’ trail. The audacious heist was by now front-page news, and the flamboyant nature of the crime led the police to immediately suspect Leishman’s involvement. Furthermore, police informants and fingerprints found in the abandoned Air Canada truck pointed directly to Grenkow and Barry. Realizing it was only a matter of time before they were arrested, the conspirators decided to fly to Hong Kong and sell the gold on the black market. This was a risky proposition, for Leishman was still forbidden by his parole terms to leave the province. Nonetheless, he decided to take the risk and booked a flight to Hong Kong for himself and the gold. On arrival in Vancouver, Leishman noticed a strong police presence at the airport and managed to ditch the gold before he was inevitably arrested. To this day, no one knows exactly what happened to the gold.

On March 20, 1966, Leishman and his four accomplices were charged with conspiracy and robbery and sent to Headingley Jail to await trial. But the “Flying Bandit” wasn’t ready to give up just yet, and on September 1 he and 10 other prisoners staged one of the most brazen prison breaks in Canadian history. After overpowering a guard and stealing his keys, the prisoners broke into the guardhouse, stole eight weapons and 800 rounds of ammunition, and fled the prison in three cars. Leishman and three prisoners made their way to the town of Steinbach where, true to form, they stole a light aircraft and headed south towards the United States. Landing in a field outside Gary, Indiana, they managed to convince a local farmer to drive them into town, where they rented a hotel room and went down to the bar to celebrate. Unfortunately, the bartender recognized the men from the news and called the police. After a brief foot chase the four men were arrested and returned to Winnipeg.

But if you think the story ends here, well then you haven’t been paying attention. While awaiting trial, Leishman was held in an empty wing of Winnipeg’s old Vaughan Street Jail, the only prisoner in the entire facility. On October 30, 1966, Leishman managed to pick the lock on the main wing door, overpower three guards using a piece of steel pipe, and escape by scaling the walls of the exercise yard. However, this escape lasted barely four hours, and Leishman was re-arrested while trying to call his lawyer from a nearby payphone. The police, baffled as to how Leishman had managed to pick the massive prison locks, asked him to demonstrate his method. In ingenious MacGyver style, Leishman had turned the bolts with nothing more than a strip of cloth and a piece of wire.

On November 1, 1996, Ken Leishman pleaded guilty to all nine charges against him and was sentenced to 15 years in prison for the gold heist, his escapes and parole violations, and the remainder of his Toronto robbery sentence. But once again the Flying Bandit managed to escape early – this time using not lock picks and aeroplanes but rather the power of the Law. After applying for and being denied parole in June 1974, Leishman requested an official review of his complicated web of overlapping sentences, some of which were to be served concurrently, others sequentially. Amazingly, the Parole Board determined that the sentences had in fact been improperly pieced together and that Leishman should be released immediately. And so, in 1975, after only nine years in prison, Ken Leishman was once again a free man.

Upon his release, Leishman at last put his criminal past behind him and moved his family to Red Lake, where he worked as a bush pilot for Tomahawk Airlines and ran a gift shop. He became a pillar of the community, serving as chair of the local Chamber of Commerce and even coming close to being elected reeve. Meanwhile, his past exploits continued to attract attention, and he was invited to make countless television appearances and newspaper interviews. Hollywood actor Darren McGavin even bought the rights to Leishman’s life story and began scouting locations for a possible movie. But when Leishman disappeared without a trace in December 1979, many suspected he had in fact returned to his life of crime and used the plane crash to make a clean getaway. But with no evidence either way, Kenneth Leishman, the Flying Bandit, was declared legally dead on December 16, 1980.

Pilot. Gentleman. Poet. Family Man. Thief. Ken Leishman lived the kind of life epic movies are made about. His audacious exploits, easygoing charm, and ‘never-say-die’ attitude captured the imaginations and hearts of the public, and forever cemented the legend of the Flying Bandit in the annals of Canadian history.

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