History’s Boldest Gold Heist: The Flying Bandit’s Great Escape

You've probably heard tales of daring heists and smooth criminals, but Kenneth Leishman's gold bullion caper stands apart. As Canada's most notorious "gentleman thief," he pulled off what many considered impossible: stealing 600 pounds of gold from a heavily guarded airport in broad daylight. His story isn't just about the gold, though – it's about how a charming small-town pilot orchestrated one of history's most audacious crimes and captured a nation's imagination along the way.

A Gentleman Among Thieves: Meet Kenneth Leishman

Kenneth Leishman, a charismatic figure born in rural Manitoba in 1931, defied the stereotypical image of a bank robber.

With his charming demeanor and an IQ of 146, he crafted a masterful dual life that captivated the public's imagination.

You wouldn't have guessed this well-dressed gentleman was anything but successful.

After dropping out of school, he worked as a traveling mechanic and even purchased his own aircraft in 1952. His childhood was marked by significant upheaval when his parents' marriage ended in divorce in 1943. During his early years, he endured a severe injury when he received a kick to the head from a horse.

In River Heights, Winnipeg, he maintained the perfect facade: a beautiful home, seven children, and a devoted wife who called him the perfect husband.

Yet beneath this polished exterior lay a calculating mind that would earn him the nicknames "Flying Bandit" and "Gentleman Bandit" – titles that perfectly captured his unique blend of sophistication and criminal enterprise.

The Perfect Storm: Planning Canada's Biggest Gold Heist

While serving time at Stony Mountain Penitentiary, Leishman crafted his most audacious scheme yet – Canada's largest gold heist. His inspiration came from watching gold shipments at Winnipeg International Airport, where Transair flights regularly delivered precious cargo from Red Lake mines to Air Canada for transport to Ottawa's Royal Canadian Mint. After successfully pulling off the heist, the thieves managed to steal approximately $385,000 worth of gold.

The heist logistics required precise timing and a trusted team. Leishman recruited four key accomplice roles: Harry Backlin as financier, John Berry and Richard Grenkow as thieves, and Paul Grenkow as the Red Lake lookout. Similar to the recent case where nine suspects were involved in Canada's largest gold heist at Pearson International Airport.

They meticulously prepared by acquiring white coveralls with stenciled Air Canada logos, stealing waybills from unmanned desks, and creating fake documentation. The team coordinated their movements to exploit security gaps during shift changes, waiting for their lookout to confirm a significant gold shipment.

The Day of Deception: Inside the Airport Operation

On March 1, 1966, as the morning shift change created its usual chaos at Winnipeg International Airport, Leishman's team executed their meticulously planned heist.

Their deceptive tactics were flawless – two accomplices donned counterfeit Air Canada uniforms with stenciled logos and drove onto the tarmac in a stolen cargo van.

You'd never have guessed they weren't legitimate employees as they confidently approached the TransAir ground crew with forged waybills stolen from Air Canada's cargo counter.

The gold was initially kept in an unassuming accomplice's freezer before being moved to a more secure location.

The heist's mastermind had recruited a lawyer and four accomplices to help orchestrate the operation.

Airport security didn't bat an eye as the team loaded 12 wooden boxes of gold bullion, weighing 600 pounds, into their van.

Within minutes, they'd driven a kilometer from the terminal, transferred the $400,000 cargo to their getaway vehicle, and vanished toward their cleaning supply business hideout.

Manhunt: The Race to Catch the Flying Bandit

The discovery of the missing gold bullion sparked the largest manhunt in Manitoba's history.

Understanding fugitive psychology, the RCMP mobilized every officer in the province, deploying sophisticated manhunt tactics including roadblocks, airport surveillance, and border crossing alerts.

You'd have thought such an extensive operation would quickly corner Leishman and his accomplices, but they proved remarkably elusive. His gregarious and charming personality had earned him widespread public sympathy during the pursuit.

Their daring escape showcased brilliant improvisation – stealing a Chevy from the prison parking lot, making it to Steinbach, and commandeering a plane to cross the border.

The chase finally ended in Gary, Indiana, where a vigilant bartender's tip led to their capture.

Two fugitives surrendered immediately, while Leishman and another accomplice attempted a brief foot chase before being apprehended.

Their audacious flight had come to an end.

Breaking Free: The Daring Prison Escape

After months of meticulous planning, Kenneth Leishman orchestrated one of Canada's most audacious prison breaks from Headingley Jail on September 1, 1966.

His escape tactics were remarkably efficient – overpowering a guard, seizing keys and weapons, and leading nine other inmates through the gates in just 15 minutes.

Prison security proved no match for his cunning.

Less than five years earlier, he had been a model prisoner at Stony Mountain Institution where he focused on education and learning trades.

You'd be amazed at what happened next.

escaping a Michigan prison, Leishman's daring breakout shocked authorities.

Leishman and three others stole a Chevy from the parking lot, made it to Steinbach, then boldly commandeered a plane to fly across the U.S. border.

They landed near Gary, Indiana, where they convinced a farmer to drive them into town.

Their freedom was short-lived, though.

A bartender's sharp eye and their Canadian currency gave them away, leading to their capture and return to Winnipeg.

The Final Flight: Legacy of a Criminal Folk Hero

Despite his efforts to reform, Ken Leishman's life ended in tragedy during a December 1979 mercy flight.

While piloting a Piper Aztec with two female passengers, his plane vanished just minutes before its scheduled landing in Thunder Bay. After a 10-day search yielded no results, the wreckage was finally discovered in May 1980, about 40 kilometers north of the city.

The final flight marked the end of Leishman's remarkable journey from notorious criminal to respected community member in Red Lake, Ontario. His position as chamber of commerce president demonstrated his commitment to community leadership. During his time in Red Lake, he skillfully operated as a bush pilot while managing a local gift shop.

You'll find his enduring legend lives on as "The Flying Bandit" and "The Gentleman Bandit," cementing his place as one of Canada's most beloved outlaws. His charismatic personality and daring exploits have inspired books, documentaries, and even a 2022 film starring Josh Duhamel.