Kenneth Leishman - The Flying Bandit (UPDATED)

William Kenneth Leishman, the 'Flying Bandit' or 'Gentleman Bandit', has been referred to as “one of the most beloved of Canadian criminals.” During the 1950s and early 1960s he committed numerous crimes, including bank robberies, plane thefts, prison breaks and, his piéce de resistance, the March 1, 1966 heist of nearly $400,000 worth of gold bouillon from the Winnipeg International Airport – the largest gold theft in Canadian history.

Instead of being labelled a public enemy, the North Kildonan cutlery salesman and father of seven charmed Winnipeggers and gained a folk hero status thanks to Canadians who fell for his smile, suave demeanor and snappy outfits !
Holland, MB ca. 1910 (Source: Peel's)

Leishman was born in Holland, Manitoba on July 20, 1931, the oldest of three children. In 1938 his parents separated and his mother took a job keeping house for a local widower. The man and seven-year-old Ken did not get along and subjected him to physical abuse.

Mrs. Leishman was given an ultimatum. In order to keep her live-in job, something hard to come by for a woman in rural Manitoba during the Depression, Ken had to go. He did and ended up in seven foster homes in one year, finally landing in a boys' home after Children's Aid seized him from an abusive home.

The Leishmans reunited for a couple of years before finally splitting and
divorcing in 1943.

Mrs. Leishman remarried, but her new husband wanted nothing to do with twelve-year-old Ken who was sent to live at his grandparents' farm. There, he received some education and a part-time job, but received a number of injuries, including two blows to the head from kicking horses that his mother later said may have accounted for some of his bad behavior, (Winnipeg Free Press Nov 2, 1966).

At age fifteen, he tried to reconcile with his father and came to live with him in Winnipeg. Things did not go well and Ken went to Kenora to work at a resort. His bad luck continued as he had to return home after breaking an ankle. Other jobs, too, ended due to injury: a merchant navy gig after a burst appendix; at a CNR yard after being struck by a boxcar, (he spent three days in a coma.)

At age 18 Ken seemed to be getting things together when he met and married Elva. Unfortunately, he stole the furniture used to furnish their first apartment and spent some of his time as a newlywed in jail, (source).

Leishman was serious about flying and set himself up as a fly-in farm machinery repairman, then salesman for a cookware company. Even though he was earning a decent income, the plane, the nice home in River Heights and his first children were hard to support given Ken's love for nice clothes and living the good life.
That's when he turned to bigger crimes.

Second Toronto Bank robbed by Leishman (Ottawa Citizen)

Though living in Winnipeg, 26-year-old Leishman planned a series of Toronto bank heists.

On December 16, 1957 Leishman flew himself to Malton Airport in Toronto, rented a car and checked into a luxury downtown hotel. The following day, after some clothes shopping, he committed what a Canadian Press story from the day called “one of the most daring robberies on record”. 

He entered the Toronto-Dominion Bank and Yonge and Albert and asked to see the manager. When introduced, he produced a gun and forced him to write a bank cheque for $10,000 and cash it at one of the tellers. He then had the manager escort him to his rental car. Leishman returned to the airport and flew himself back to Winnipeg.

In March 1958 he again flew out and robbed another Toronto bank at the busy intersection of Bloor and Yonge. A teller was able to press the emergency alarm and Leishman was caught on the pavement outside the bank after tripping over a woman.

April 17, 1958, Winnipeg Tribune

Leishman plead guilty to the two robberies, no one was sure if there were more, and was given a 12-year sentence to be served at Stony Mountain Penitentiary in Manitoba, near his family. He was paroled after just 3.5 years, described by Stony’s warden as a ‘model prisoner’.

Leishman's next brush with crime, as far as the public knew, was an arrest for parole violation when he left the province of Manitoba in 1966. He was picked up by RCMP when he got off a commercial flight in Vancouver. On March 11, 1966 the Mounties escorted him back to the city in what a Free Press story of March 12, 1966 called "one of the hushiest hush-hush police operations on record in Winnipeg."

March 2, 1966, Winnipeg Free Press

While proceedings to have Leishman returned to Stony Mountain to fulfill the remainder of his 12-year sentence went on in the courts, Winnipeg police were working hard to get him for something bigger; the Winnipeg Airport gold heist of March 1, 1966.

Leishman had been planning the heist for years. He knew that regular TransAir flights of gold bullion were made from Red Lake, Ontario to the Winnipeg Airport where it was transferred to an Air Canada flight bound for the Royal Canadian Mint in Ottawa. Working with four accomplices, Leishman's plan involved the impersonation of Air Canada employees complete with home-made ground crew uniforms and a stolen Air Canada cargo van. 

When the flight arrived, they drove onto the tarmac, showed some doctored paperwork and even had two TransAir employees help them load the 12 boxes from the plane to the van before driving off.

March 22, 1966, Winnipeg Free Press

The crime may have appeared simple, but the aftermath was anything but.  

The abandoned Air Canada van was found soon after, with a fingerprint inside, and the police were zeroing in on a couple of suspects. They favoured Leishman as the mastermind behind the heist. To make matters worse, Winnipeg was experiencing bad weather which culminated in the legendary Blizzard of 1966 two days later, making the plan to properly hide the gold bars impossible. 

By the time Leishman was arrested in B.C. the police already had his four accomplices and the 12 bars of gold in their possession. On March 20th Leishman was charged with conspiracy and robbery.

Sept 2, 1966, Winnipeg Free Press

While awaiting trial at Headingley Jail, Leishman masterminded the escape of ten prisoners, himself included. On the evening of September 1, 1966 one member of the group overpowered a guard and within 15 minutes they had made their escape. Some were on foot but Leishman left in a Chevy that he stole from the prison grounds.

News of the escape set off what is believed to be Manitoba's largest manhunt. Every municipal police force was placed on high alert and told to set up road blocks at the perimeter of their communities. The RCMP called in every on and off-duty officer and manned their own roadblocks on highways throughout southern Manitoba. Bordering provinces and states were also alerted, (as Leishman was an experienced pilot.)

Returned from Indiana (source)

Leishman made it to Steinbach, stole a small plane and with three other escapees, (
a murderer, a rapist and someone awaiting transfer to Selkirk Mental Hospital), headed for Gary, Indiana. They were discovered the next day when a bartender recognized Leishman from news coverage. After a stand-off, the men were captured and returned to Winnipeg.

The arresting officers (source)

Leishman again escaped custody, this time from the Vaughan Street Jail on October 30, 1966. The only prisoner in that wing of the detention centre, Leishman was allowed access to the corridor outside his cell for exercise. One day he managed to open the door at the end of the corridor, overpower three guards and escape over a fence. (By this time, he was receiving international attention for his moves.)

St. James Police Department mug shot

Four hours after the break, Leishman was caught at a phone booth at Main and Jefferson. The next day, jail administrators had experts go over the door to see how he managed, without a key, to turn the locking bolts and mechanisms on the ancient door. They said it was 'miraculous' that he was able to do it. (After his conviction they had Leishman re-enact his MacGyver-esque escape for them. He used a strip of cloth and piece of wire.)

On November 1, 1966 it was announced that Leishman was pleading guilty to all nine charges against him. He received a total 14 year sentence, eight for the gold heist and escapes, plus six for the original Toronto robbery and parole break.

November 2, 1966, Winnipeg Free Press

Leishman spent his years in prison reading and writing poetry.

In June 1974 he applied for parole and was denied. He then requested an official review of the length of his sentence as his time in jail was a complicated mesh of various sentences spanning years. Some allowed for time to be served concurrently, some not. Leishman struck gold a second time when the Parole Board ruled that, indeed, his sentence had been improperly pieced together and that he was to be released immediately ! The ruling sparked a review of hundreds of similar sentences around the country.

In 1977 Ken moved to Red Lake with his wife and two of their children to take a job as a pilot and opened a tourist shop. He was well liked by community members and even served as chair of the local Chamber of Commerce.

On December 14, 1979, Leishman was performing a medivac flight out of Red Lake when his plane disappeared in Northern Ontario. The following spring a Canadian Forces search flight found the wreckage. The bodies of the patient and medical assistant aboard 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 had escaped again. At the inquest, however, experts concluded that his body was likely taken away and eaten by wolves.

On December 16, 1980, Leishman was declared legally dead at the age of 48. He left behind his wife of 30 years, seven children and quite a legend.

His obituary, which makes no mention of the time before his release in 1977, includes a poem written by Leishman:

The day's are long and endless
And the sun does not take rest
Tis a barren hostile country
And man is put to test.

Yet there's a compelling remote beauty
In this land so fresh and clean
With it's waters pure as crystal
And trout that few have seen.

I've drunk of nature's beauty
And I've suffered natures pests
I've co-existed with God's creatures
And I've met and passed the test.

But this is a land of special beauty
It's a land for special men.
When I leave I'll do so gladly
But I know I'll come again.

I'll bear memories of kind people
Of sunsets without end
I'll respect and fear the northland
And I'll do so as a friend.

Source: Winnipeg Free Press, May 7, 1980

Update 2011:

I originally posted this in 2008, (this is a 2011 update.) Since then, it has remained one of my most popular posts showing that there is still a great interest in the man and his antics.


I wasn't around at that time, so I can only guess that being an everyday man, (a cutlery salesman in a modest home in North Kildonan with a wife and kids), pulling off crimes usually reserved for Hollywood movies was a huge factor. He also has the sad luck of always getting caught, coupled with the good luck of 'the system' always coming out in his favour. Mix in a dose of style and charm that seemed to enthrall people and you really had quite the figure.

As you will see in the comments below, and I have had from emails that I have received behind the scenes, the charm offensive was not something just for the cameras or part of his criminal persona. He appears to have been a genuinely charming person, well liked and respected by those who knew him.

Online news stories

Ottawa Bound Bullion intercepted at airport 
Canadian Press, March 1966

He went on business trips - to rob banks
Saturday Magazine, Ottawa Citizen, July 18, 1958

Flying Bandit out again - this time it's legal 
Canadian Press May 1974

Other items

RCMP Court Briefing for 1966 Trial of Ken Leishman et al

The Flying Bandit - What Next? blog

Additional Media
- a play (The Flying Bandit, by Lindsay Price);
- a book (The Flying Bandit by Heather Robertson);
- a documentary (Ken Leishman: The Flying Bandit - trailer above).
- at the time of his death, the late actor Darren McGaven had the film rights for a movie on Leischman's life.


Anonymous said...

This article brings back some old memories. I well remember the days of "The Flying Bandit" and the gold heist. If I'm not mistaken he was also elected as the mayor of Red Lake when he was there. I also don't seem to recall if his body was ever positivly identified since I don't believe all 3 bodies were recovered from the crash site.

JR said...

You are right no bodies were ever recouvered from the crash site, only some personel effects ie: wallet, watch and purse. I was part of the crew on the serach and rescue helicopter that found the site the followin spring.


Anonymous said...

Ken Was My Dad's Cousin, I Remember Canada Post Coming To Our House In The Early 80's With A Parcel. Inside That Parcel Was Something That Made My Dad So Happy, It Was The Book The Flying Bandit With His Cosins Signature "" To Big John ( Al ) I'll See You Sone"" The Initials J,R Are My Dads And It's True No Body"s Were Ever Found

Lorne Ransome

mrchristian said...

That is so interesting. I guess if he were to disappear a touch of mystery would have been appropriate. If we lived in the US the guy would be a hollywood folk hero !

Tyler said...

I'm sitting in a pub in Winnipeg with a man who just told me this story. It's Ken Leishman's son. I looked this up on my phone wanting to know more. This has turned out to be an amazing night.

mrchristian said...

That's very cool ! I will have to keep my eyes an ears open at local pubs from now on !!

Anonymous said...

Glad to see someone is keeping his memories afloat. My Mom tells me stories of when they hung around together with my Dad. My Mom remembers Ken inviting them over to his apartment to see all the new furniture him and his wife bought. My Mom never new he stole it from Eatons! LOL. She said he was the nicest man. They lost touch after my parents moved to Ontario.

Anonymous said...

I lived in Red Lake from 78 to 81. Ken made a t shirt for me at his store. A month after he was legally declared dead ( 1 year after the crash, his body was never found) his wife sold the store in Red Lake and moved to California.

mrchristian said...

Thanks to everyone who has commented on this post. It's great to hear more about the man !

Today I have done a major updating of the post. Lots of new material !

Fat Arse said...

An excellent read, thoroughly enjoyed it. Who says our history is boring? Not me. Well done.

winnipegcrime said...

Truly a great post. Fascinating guy.

Loryl Shields Tkachuk said...

So glad I came upon this. Ken's wife Elva Shields was a 1st cousin to my father. They often visited my parents & older siblings. Being the youngest in my family I only have one memory of him which would have been around 1978-79 when he got out of jail. I would have been 10 yrs old.There was a big party at a house & his son had a pet tarantula that he left out under some papers on a coffee table. LOL. In walked Ken & I remember how distinguished he a movie star with his pencil thin mustache. My parents had said that he had asked my dad once if he would be able to store some gold bars on the farm, apparently my dad didn't want any part of it. (Must have been a thought when planning their big heist.) I remember when the news story broke in 1980 that his plane crashed and watching it on TV....their sons walking through the snow looking for the plane. Elva & their kids still keep in touch with my mom. Over the years its been great hearing the stories & getting to know the man behind the mustache. Makes for a great movie someday.

Kerry White said...

Ken's wife, Elva, is my husbands aunt. Ken and Elva attended our wedding in 1979.
Ken was a fun loving exuberant person and he was missed by his family when he died in the plane crash.
Elva is still living in California.

Anonymous said...

I first met Ken Leishman after he was released from prison and came to Sioux Lookout to resume his flying career. He was employed with the same company as my husband and often came to our home along with the other pilots. He was one of the most charming and likable men I have ever met. His wife occassionaly came for a visit and she too was a delightful, fun-loving person who obviously adored her husband. In early 1979 I was doing a medi-vac to Winnipeg in a Piper Aztec that went down into a lake.Fortunately I survived. Among the first people to call me were Ken and Elva Leishman, who were living in Red Lake by then. Ken promised to make me a t-shirt in his shop with my picture as "Lady Aztec" on it; something I never received as later that same year he too went down in a Piper Aztec but sadly did not survive.

Anonymous said...

I enjoyed reading the article. I am Ken's granddaughter and I was just looking to see if I could find any great photos of him online and came across your article. By the way, Grandma's name is Elva, not Alva.

mrchristian said...

Thanks anon. Nice to hear from you. I have made the correction to Elva's name.

Anonymous said...

Yes it is does bring back many memories. The kitchen cookware set, sure does he used to sell kitchen queen. Good cokeware.

Fred Dalkeith said...

I was attending Red River Community College at a Sales Course when the students were required to introduce themselves to the rest of the class. Ken stood up, buttoned his suit jacket and said, "Good Morning. My name is Ken Leishman. Perhaps you've heard of me". At that time he was on a temporary absence from Stony Mountain. The whole class cracked up.

Anonymous said...

he has been seen (by someone who has met him in Steinbach, MB years ago) working in a jewelry store in Victoria, BC... great place to sell his stolen gold turned into jewelry.

Anonymous said...

There's a dentist in White Rock/Surrey. Is he the same person that robbed Air Canada?

mrchristian said...

He died in 1979, so it wouldn't be him !

Anonymous said...

I grew up in Red Lake. My grandparents also ran a store in Red Lake, and knew Ken while he was there (I was born in 1990, so never had the chance to meet him personally).

My grandmother always said he was extremely nice, and even though he was technically a thief, "You were still comfortable letting him in to your home because you knew he would only ever take from those who could afford it."

Anonymous said...

I work with Kens son, heard some fascinating stories about the man!

samsan crow said...
This comment has been removed by a blog administrator.
Anonymous said...

I know an Elm Creek man that was best friends of Kenny in their childhood years and still believes that some of Kenny's gold ingots are buried under a YVR runway. He also became a pilot because of Kenny. Another Winnipeg man I know used to date a daughter of Kenny in his teens. I live very far from Winnipeg but he is well known to me.

Bob Barker said...

Ken came from Holland Manitoba, the same farming village I grew up in.
I had heard many stories about Ken while I was growing up from the local people as well as my parents. Every body seemed to like "Ken"
The locals kinda sat back to see what he was going to do next (:-).
It is too bad that we don't have more down to earth people such as him.

thedevilcorp said...

Good site.

Anonymous said...

I am ken Leishman.

I survived the crash and hitchhiked to B.C. My injuries from the crash were fairly severe and rendered me unrecognizable.

I sell jewelry and keep a low profile.

My work is not done.

Shelley McKenzie said...

I live in Red Lake and as youngsters we had very little. My older sister who couldn't be more then 13 at the time when she bought me a t-shirt from Ken Leishman's store. It was blue t-shirt that had a puppy on it holding a heart and it said "puppy love". I was so proud of that shirt. My sister later told me that Mr. and Mrs. Leishman allowed her to charge the t-shirt so she could buy it for me. Now...doesn't that say a lot of a man and of his wife. My sister paid for it but really...who lets a 13 year old open a charge account. Mr. Leishman was a good man and died trying to save someone else's life. May he rest in peace.

Randy Chevrier said...

Ken was a personal friend of my parents. We spent many hours houseboating and sitting around the campfire. He was one of the most interesting people I have ever met. He was very highly respected in red lake.

Randy Chevrier said...

Ken was a personal friend of my parents. We spent many hours houseboating and sitting around the campfire. He was one of the most interesting people I have ever met. He was very highly respected in red lake.

Anonymous said...

Mr. Kenneth Lieschman was a con artist smooth talker and genuine thief. I was in Red Lake in 1977 and he was alive and had a store there. He \is book the flying bandit has a lot of false information(of course he's a criminal , he would lie.) the gold was never all found and his partners. This was known in Wpg. He had different businesses and was a major criminal who should of been held in prison for the crimes he committed . unfortunately I had the undue pleasure of knowing this criminal and having him inflict his torment in my and our lives. I have no respect for him or his family.

Big bad John said...

He also had family in Treherne Manitoba the Gates family I believe.

Anonymous said...

I remember him well, I worked with him as a salesman at Silverline Mfg. (selling furnaces) My wife and used to go bowling with Ken and his wife. One of the nicest man you could go out with, that was around 1961.

j lander said...

He was my cousin it seems.(5th)
Interesting what can be found on the family tree.