© 2008, 2011, 2026, Christian Cassidy. Please respect my research.
I first wrote this post back in 2008, (before West End Dumpling even existed!) and have updated it a couple of times over the years to fix broken links and other formatting issues. It is likely my most popular post, as it still falls inside my top 20 most-read blog posts each year, and I am often asked to contribute to news stories about Leishman. I thought it was finally time to bring it over to West End Dumplings on the 60th anniversary of Leishman's great heist!
I will leave the old post up as it has generated many comments over the years, some from people who knew Ken!
William Kenneth Leishman, also known as the 'Flying Bandit' or 'Gentleman Bandit', has been referred to as “one of the most beloved of Canadian criminals.” This is thanks to his family man persona and polite demeanour.
In the 1950s and early 1960s, he committed numerous crimes, including warehouse thefts, bank robberies, and prison breaks. His piéce de resistance was the March 1, 1966 heist of nearly $400,000 worth of gold bullion from the Winnipeg International Airport, which was the largest gold theft in Canadian history until a 2023 heist at Toronto's Pearson International Airport.
Instead of being labelled a public enemy, the North Kildonan kitchenware salesman and father of seven charmed Canadians and gained a sort of 'criminal folk hero' status, which is pretty rare in this country.
Here is a look back at the life of Ken Leishman.
William Kenneth Leishman was born on a farm in Holland, Manitoba, on July 20, 1931, to Norman Allan Leishman of Treherne and Irene Beatrice Agarand of Holland.
The couple married in Winnipeg on September 25, 1928 and the 1931 census entry above shows them, just weeks before Ken was born, living at the Agarand farm with daughter Elizabeth. They would go on to have a third child named Robert.
Norman was good with his hands and worked fixing farm machinery.
Holland was a pretty typical Manitoba farming community. At the time, had at least three or four grain elevators that were serviced by the two railway lines that passed through town. It also had a bustling Main Street thanks to the 400 or so area residents.
This prosperity changed as the Depression wore on. The effects of drought and bottomed-out commodity prices rippled from farmers to farm workers to townspeople.
Norman and Irene separated in 1938, not long before he went off to serve in the Second World War, and they divorced in 1943. This left Mrs. Leishman in the terrible predicament of being a single mother of three in rural Manitoba at the tail end of the Depression.
She made what must have been a wrenching decision to send Ken into foster care and he bounced from foster home to foster home, then landed in a residential orphanage after Children's Aid seized him from an abusive household.
After the Leishman divorce was granted in 1943, Irene married William "Bill" Brooking of Treherne, Manitoba. He, too, had issues with Ken and at age 14, he was sent to live and work back on his grandparents' farm.
The farm brought a stability to Ken's life, though he was prone to accidents. One time he was kicked in the head by a horse, something Irene claimed in the 1960s may have accounted for some his bad behavior (source: Winnipeg Free Press Nov 2, 1966).
At age 16, Ken tried to reconcile with his father and came to live with him in Winnipeg.
Norman had served with the A15 Infantry Training Centre at Shilo, Manitoba, where he reached the rank of lance-corporal. There, he met Norah Nancy Michels, who had enlisted with the Canadian Women's Army Corps and was also assigned to Shilo. The two married in 1944.
After the war, the couple settled in Winnipeg, where Norman worked for Western Elevator and Motor Company and Norah for Eaton's. They initially lived in a small apartment on Garry Street before moving to a house on Lipton Street in the West End. Ken stayed with the couple on Lipton Street.
In the summer (likely of 1947) Ken went to cottage country to work at a resort in Kenora. He ended up breaking his ankle not long into the job and had to return to Winnipeg.
Wedding photo (Source: Leishman family, Calgary Sun archives)
At age 17, Ken returned to one of the towns he stayed at when he was a child, likely Holland or Treherne, to attend a funeral. There, he met Elva Shields, who would later say that it was "love at first sight". The two stayed in touch and were married on February 25, 1950, in Winnipeg.
Elva got a sign of things to come when Ken spent a few months of their newlywed year in jail.
Ken worked part-time with his father at the elevator repair company, which gave him access to a variety of buildings. He cased the interior for products he wanted, then came back after hours to break in and, posing as an employee of that company, called a transport company to deliver the goods to the couple's suite on Gertrude Street.
In February 1950, weeks before his wedding, his thefts included: a radio from a downtown building; a fridge and range from the Westinghouse building; a chesterfield suite, dinette suite and chairs from a Genser's warehouse on Market Street; a bed and kitchen suite from the Genser's warehouse on Ross Avenue. The total value of the goods was just under $1,000.
The arrest came in early March while at a return visit to Genser's Ross Avenue warehouse. The transport company dispatcher was suspicious of getting a call so late at night and tipped off police.
Ken pleaded guilty and was sentenced to nine months in jail. He apparently got out in three due to good behavior.
After his release, Ken pursued another interest of his: flying.
It is unclear where this love came from. He could have been exposed to small planes in his youth through crop-dusters servicing Manitoba farmland. It could also have been during the Second World War when southwest Manitoba was dotted with hangars, airfields and control towers for the British Commonwealth Air Training Plan.
Ken took flying lessons, bought a plane, and began a series of fly-in machinery repair and sales jobs to rural communities. (In October 1953, he received a two-year suspended sentence for flying without a pilot's license - it is unclear whether he obtained one after that, or if he just kept flying.)
Winnipeg street directories show that through the 1950s, the Leishman family lived at various addresses, usually a new one every year. They included: 752 Seven Oaks Avenue in West Kildonan (1951–1952), 113 Roberta Avenue in East Kildonan (1953), 661 Pembina Highway (1954), 525 Castle Avenue in Elmwood (1955), 1904 Dawson Road near Navin (1956), and 874 Lindsay Street in River Heights (1957).
When Ken first got out of jail, he was a switchman with the CNR, then in 1951 he rejoined his father, who had become general manager of Mid-West Elevator. He worked at both the elevator company and seasonally for several companies and flew into rural and remote communities to do machinery repairs or sell things like cutlery, pots and pans, and household utensils. The companies were Machine Industries, International Steel, Reno Wear Distributors, and Ken-Mae Enterprises.
In March 1957, Ken was a member of the newly founded Manitoba Volunteer Air Patrol, a civil defense organization, and was in charge of organizing a national meeting in Winnipeg on the topic of having a nationwide VAP. This involved meeting high-level officials in Ottawa.
December 18, 1957, Canadian Press
Outward appearances were that Ken was doing well with a big family, a house in the suburbs, a plane, a Cadillac and an expensive wardrobe. The truth was that he was living well beyond his means and in 1957, he started to supplement his income by robbing banks.
Ken decided that he would go to Toronto to commit the robberies. He later told police that while Manitobans had money, it was usually tied up in land, equipment and other investments. Toronto, he felt, was where cash flowed more freely.
In December 1957, he boarded a commercial flight to Toronto, rented a nice car and checked into a luxury downtown hotel. The following day, after some clothes shopping, he committed what the Canadian Press reported was “one of the most daring robberies on record.”
Posing as "Mr. Gair", a Buffalo businessman, he entered the Toronto-Dominion Bank at Yonge Street and Albert Avenue and asked to meet with the manager. Inside the office, Ken produced a gun, forced the manager to write a cashier's cheque for $10,000, and stayed with him while he cashed it at one of the tellers. He had the manager escort him to his car, then wished him and his family a very Merry Christmas before speeding off.
Witnesses described Ken as well-dressed, polite and dignified, which led to the "Gentleman Bandit" nickname.
Ken returned the car and took his return flight to Winnipeg that evening. His family thought he had been on one of his fly-in sales jobs.
While fleeing the building, Ken tripped over someone on the sidewalk. Another pedestrian, a minister, kicked the gun out of his hand. Bank staff then held him until police arrived.
Ken's arrest and the exploits of "The Flying Bandit" were front page news across the country. The fact that this daring robber wasn't some gangster, but a well-dressed kitchenware salesman from River Heights, gave the story extra life.
As for Elva, who was expecting the couple's sixth child at the time, she claimed she knew nothing of the robberies and only learned about his arrest when two of her children came home from school in tears after having been teased about it by fellow students. She said, "I never pry into his affairs. He is a perfect husband and father and just a wonderful guy."
Ken pleaded guilty to the two robberies and he was given a 12-year sentence at Stony Mountain Penitentiary. He was paroled in just 3.5 years after being described by Stony’s warden as a ‘model prisoner’.
To put food on the table while Ken served his sentence, Elva operated Elva's Gift Shop at 2635 Portage Avenue in St. James.
After jail, Ken went back to fly-in sales with a company called World Wide Distributors, selling kitchenware and silverware. After a couple of years with the company, he was made a supervisor and the family purchased a new home at 482 Mark Pearce Avenue in North Kildonan.
Despite appearing to settle down, Ken was actually plotting his biggest caper yet.
March 12, 1966, Winnipeg Free Press
The next time Winnipeggers saw Ken Leishman on the front page of the papers was in March 1966, after he was arrested at Vancouver's airport for a parole violation. He was returned to the city under RCMP escort on March 11 in what the Winnipeg Free Press called "one of the hushiest hush-hush police operations on record in Winnipeg."
Proceedings soon got underway to return Ken to Stony Mountain to fulfill the remainder of his 12-year bank robbery sentence, while Winnipeg police worked behind the scenes to charge him for something bigger: the Winnipeg International Airport gold heist of March 1, 1966.
Through his connections in the local aviation community, Ken knew that TransAir, an airline that connected Northwest Ontario and Winnipeg, regularly flew gold bullion from Red Lake, Ontario, to the Winnipeg International Airport where it was transferred to an Air Canada Cargo flight bound for Ottawa and the Royal Canadian Mint. (This was a decade before the mint's coin striking facility opened in Winnipeg.)
Ken's plan was both daring and simple: intercept the gold on the tarmac and drive off into the sunset.
Unlike his previous thefts, Ken needed accomplices for this one. They included three bar buddies and a Winnipeg lawyer named Harry Backlin. While studying law, Backlin visited prisoners at Stony Mountain. He and Ken hit it off and even went into business together after Ken was released in a cleaning supplies wholesale company.
Items required for the heist were assembled. Blank waybills were taken from an Air Canada Cargo counter. Two pairs of white coveralls, similar to what Air Canada Cargo ground crews wore, were purchased and crude Air Canada logos were stencilled on using red markers. The parking lot where the airline kept its cargo vans after hours was also scouted.
An accomplice in Red Lake tipped Ken off that a TransAir bullion flight would arrive in Winnipeg on the night of March 1, 1966, and the plan was put into motion.
Before the flight touched down, two of the bar buddies hotwired an Air Canada Cargo van and drove onto the tarmac through a back gate. They met the plane, showed the TransAir crew a fake waybill, and the gold was loaded into the van.
The two drove away with nearly $400,000 in gold bullion, each of the twelve bars in its own wooden box. It was Canada's largest-ever gold heist. (Edit: It may still be Canada's largest. The 2023 Pearson International Airport heist made off with $23 million in gold and some call that the largest. To compare apples to apples, you would need to take the number of ounces stolen in 1966 and put it through a gold inflation calculator to find its 2023 value.)
After the heist, the two men drove about a kilometre away where they had stashed a getaway car. The gold, which weighed about 600 pounds, was transferred in its boxes to the new vehicle and driven to the small warehouse that Ken and Backlin ran their cleaning supply business out of.
The plan was for Ken to then drive the gold to the farm of a relative of Backlin's a couple of hours away from the city, but Mother Nature interfered.
A Colorado Low was sweeping into the province with strong winds and heavy snowfall. In the next 24 hours, it would become one of Winnipeg's worst blizzards.
Ken knew that minutes after the heist, when the real Air Canada Cargo crew showed up for the gold, the alarm would be raised and that could mean Winnipeg Police or RCMP roadblocks. With the car heavily weighed down and the weather worsening, he realised it would be a much longer and riskier drive than he had anticipated.
The "plan B" was to take the gold to Backlin's home at 119 Balfour Avenue in Winnipeg's Riverview neighbourhood. Backlin was out of town and unaware of the plan, but his mother was housesitting. She opened the door for Ken, who told her he had the boxes of moose meat that Backlin had ordered. He was shown the chest freezer in the basement and stashed the gold there.
When Backlin returned home, he was unimpressed with Ken's decision and took the gold and buried it in the snow in his back yard to avoid raising his wife's suspicion.
The two men had to act fast as the snow wasn't going to stay around for long in early March. They decided to forego stashing it somewhere else for the longer term and instead try to sell it on the black market in Hong Kong.
Unfortunately, both men had passport issues.
Backlin had recently anglicized his name, and his old passport was at the passport office while he awaited a new one. Ken was still on parole, and if someone checked the name on his passport they would find that he could not leave Manitoba, much less the country.
Desperate to get rid of the gold in a hurry, they decided to take a chance. Backlin bought a ticket to Hong Kong, and Ken travelled using his own passport.
Ken reached the Vancouver airport with part of one of the gold bars in his luggage to show potential buyers the quality of his product. Some sources say he noticed a strong police presence, others say that he was paged over the PA system to report to customer service. Whichever it was, Ken got spooked and ditched the gold outside the terminal. To this day, nobody knows what happened to it.
The RCMP closed in, and to Ken's surprise he was arrested for parole violation with no mention of the gold.
Ken was returned to Headingley Jail for the parole violation and was awaiting his hearing that would return him to Stony Mountain to serve out the rest of his "flying bandit" sentence. Behind the scenes, Winnipeg police were working hard to pin the gold heist on him.
The abandoned Air Canada van was found with a fingerprint of one of the accomplices inside. Police eventually tracked down the two drivers, and through interviews and the use of a cellmate informant, the story of the heist was laid bare.
On March 20, 1966, Ken and four accomplices, including Backlin, were charged with conspiracy and robbery. Of the twelve bars of bulion, ten were dug up from the snow drift behind Backlin's house and another was found at his Portage Avenue office. Part of the twelfth was ditched by Ken at the Vancouver International Airport and it is unclear what happened to the rest of it.
The arrest of Backlin was quite newsworthy as he was a fairly well-known lawyer by that time. The man who defended him in court was a young Roland Penner, who would go on to be a long-time Manitoba MLA and attorney general.
September 6, 1966, WInnipeg Free Press
While at Headingley Jail, Ken masterminded the escape of ten prisoners, himself included.
On the evening of September 1, 1966, one member of the group overpowered a guard and stole his keys. Others entered the guard office and stole weapons. Within fifteen minutes, they were outside the gates.
Ken, along with three other prisoners (a murderer, a rapist, and someone awaiting transfer to Selkirk Mental Hospital) stole a Chevrolet from the prison parking lot and took off. This started what is believed to be Manitoba's largest manhunt.
Every municipal police force was placed on high alert and told to set up roadblocks at the perimeter of their communities. Manitoba RCMP called in every officer on the force and manned their own roadblocks on highways throughout southern Manitoba. Bordering provinces and states were also alerted.
Ken and company made it to Steinbach, where he stole a small plane and the four headed across the border. They landed in a farmer's field outside Gary, Indiana, where Ken sweet-talked the farmer into giving them a ride into town.
The men rented a hotel room and went down to the bar to celebrate. The bartender recognized them from a news report. Their use of Canadian bills to pay for their room and drinks helped confirm his suspicion.
When police arrived, Ken and one of the escapees gave themselves up. The other two led police on a foot chase and were captured. The four arrived back in Winnipeg on September 9, 1966.
Ken found himself at the Vaughan Street Jail awaiting his hearing for an even longer list of charges. By this time, the jail was used mainly as a remand centre, as Winnipeg's Public Safety Building had just opened, so Ken was held in an empty wing and had access to the corridor outside of his cell.
On October 30, 1966, Ken picked the lock on the old steel door at the end of the hall, overpowered three guards, and escaped through a back door to freedom.
Four hours later, Ken called his lawyer from a phone box at Main Street and Jefferson Avenue. The lawyer either convinced him to give himself up, or he turned him in, as minutes later two officers from the West Kildonan Police Department showed up and Ken surrendered peacefully.
The next day, jail administrators had experts examine the massive, ancient steel door to see how Ken managed to turn the locking bolts. They were baffled and called the escape 'miraculous'. (After his conviction, Ken was asked to demonstrate his MacGyver-esque moves for them. He used just a strip of cloth and a piece of wire.)
On November 1, 1966, Leishman pleaded guilty to all nine charges against him. He received a sentence of nearly 15 years, seven for the gold heist and escapes, plus the remaining eight years left on his Toronto bank robbery sentence.
Ken spent his years in prison reading and writing poetry, but he had one more escape up his sleeve.
In June 1974, he applied for parole and was denied. He then requested an official review of the length of his sentence, which was a complicated web of various sentences dating back to Toronto, some to be served concurrently and some not. The parole board panel did the review and found that his sentence HAD been improperly pieced together at his last sentencing. It ruled that because of the error, Ken should be released immediately!
The ruling sparked a review of hundreds of similar sentences across the country.
After his surprise release in 1974, it appears that Ken was ready to settle down and make up for lost time with his family.
By 1977, the Leishmans had moved to Red Lake, Ontario, where Ken took a job as a bush pilot and opened a tourist gift shop that he ran with Elva. The couple, who became devout Mormons, were well-liked by community members. Ken served as the chair of the local Chamber of Commerce for a time and lost a 1978 bid to become reeve by just 75 votes.
There was also time to enjoy wider-scale notoriety of being the 'Flying Bandit', the mastermind behind Canada's largest gold heist, and an adept escape artist. There were newspaper and magazine interviews, and likely his biggest audience was on the February 21, 1977 edition of the short-lived Peter Gzowski TV talk show, 90 Minutes Live. (Sadly, that clip has disappeared from the internet.)
Ken had become a folk hero. A charming but unassuming family man who tried his best to "stick it to the man" by robbing banks, stealing from the mint, and breaking out of jail. All done with a healthy dose of Canadian courtesy and manners.
Ken was working on a manuscript about his life in 1979, and according to Tribune entertainment columnist Gene Telpner, actor Darren McGavin bought the rights to the story. Ken said that he and his wife went to California to meet McGavin and potential filming locations were being scouted north of the border. It is unclear what happened as the project never materialised. (And, surprisingly, nobody else from Hollywood has ever picked up on Leishman's story in the decades since!)
Ken continued to fly and performed midi-vac flights for the area.
On December 14, 1979, he was performing such a flight with a twin-engine Piper Aztec from Sandy Lake First Nation to Thunder Bay when his plane disappeared. Several searches of the dense bush were done, but it was not until spring that a Canadian Forces search flight found the wreckage.
The bodies of the patient and medical assistant were positively identified, but all they could find of Leishman was his wallet and some scraps of clothing.
Given his colourful past, there was speculation that the Flying Bandit may have escaped again. At the inquest into the deaths, however, experts concluded that he likely could not have survived the crash, much lass walk for hours through the dense bush. It concluded that his body was likely taken away and eaten by wolves.
On December 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.
Elva Leishman moved to Gridley, California, in 1980, where her daughter and family lived, and remarried. She died in 2021 at the age of 93.
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