Kenneth Leishman - The Flying Bandit (UPDATED)

© 2008, 2011, Christian Cassidy

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.”

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 latter was, and remains, the largest gold theft in Canadian history.

Instead of being labelled a public enemy, the North Kildonan kitchen wear 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. In 1938, his parents separated and his mother took a job as a live-in housekeeper for a local widower. The man and seven-year-old Ken did not get along and the boy was subjected 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 began a childhood of bouncing from foster home to foster home, eventually landing in a boys' home after Children's Aid seized him from an abusive household.

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 12-year-old Ken. He again was sent away, eventually ending up living and working on his grandparents' farm at the age of fourteen. Life was relatively good there, though Ken received a number of injuries, including a kick in the head from a horse. His mother later said this may have accounted for some of his bad behavior, (Winnipeg Free Press Nov 2, 1966).

At age 16, he tried to reconcile with his father and came to live with him in Winnipeg.

Later that year, he was off 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 Great Lakes ship gig after a burst appendix and a CNR yard worker after being struck by a boxcar and knocked unconcious.

At age 18, Ken seemed to be getting things together when he met and married Elva Shields. Unfortunately, he stole the furniture used to furnish their first apartment and spent a few months of their newlywed year in jail.

Leishman loved flying and got his pilot's license and eventually bought his own plane. He sought out jobs that enabled him to fly into rural communities, such as salesman or repairman.

Even though he was earning a decent income he was falling onto debt. The plane, a Cadillac, suburban home and Ken's love for nice clothes and living the good life were all too much when he had, at the time, five children to feed.

That's when he decided to start robbing banks.

Second Toronto Bank robbed by Leishman (Ottawa Citizen)

Leishman decided to rob the banks in Toronto, later telling police that while Manitobans had money, it was usually tied up in land, equipment and other investments. Toronto was where cash flowed more freely. In December 1957 Leishman boarded a plane to 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 called “one of the most daring robberies on record”. 

Posing as "Mr. Gair", a Buffalo businessman, he entered the Toronto-Dominion Bank at Yonge and Albert and asked to meet with the manager. In his office, he produced a gun, forced him to write a bank cheque for $10,000 and stay with him while he cashed it at one of the tellers.

Leishman returned to the airport and flew back to Winnipeg that night to a family who thought he was off on a repair trip to rural Manitoba.

In March 1958, he was back in Toronto and tried to rob another bank at the busy intersection of Bloor and Yonge. This time, the manager became angry when the gun was produced and sounded the alarm. While fleeing, Leishman tripped over someone on the sidewalk outside and was held by bank staff until the police arrived.

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 near his family at Stony Mountain Penitentiary in Manitoba. He was paroled after just 3.5 years, described by Stony’s warden as a ‘model prisoner’.

Leishman's next brush with the law came in March 1966 when he was arrested for  parole violation at Vancouver's airport after arriving on a commercial flight. The RMCP retunred him to Winnipeg on march 11, what the Free Press referred to as "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 bank robbing sentence were underway, 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. It was then 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, two of the men drove onto the tarmac, showed some doctored paperwork, and even had two TransAir employees help them load the 12 bars of gold worth $383,000 from the plane to the van before driving off.

It was Canda's largest-ever gold heist.

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 with a fingerprint inside and police were zeroing in on a couple of the accomplices. To make matters worse, Winnipeg was experiencing a winter storm which culminated in the legendary Blizzard of 1966, 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 11 bars of gold in their possession. Leishman, it turns out, was off to Hong Kong with a twelfth bar of gold to broker a sale on the black market. (That 12th bar of gold was never found, it was assumed he was suspicious of the RCMP presence at the airport and buried it outside.)

On March 20, 1966, 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 stole his keys. Others entered the office and stoll weapons. Within 15 minutes, they were outside the gates. Leishman, along with three other prisoners,
a murderer, a rapist and someone awaiting transfer to Selkirk Mental Hospital, stole a Chevy from the prison parking lot.

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 officer and manned their own roadblocks on highways throughout southern Manitoba. Bordering provinces and states were also alerted as were airports.

Returned from Indiana (source)

Leishman's crew made it to Steinbach where he stole a plane the four headed across the border.

The following day, a bartender in Gary, Indiana
recognized Leishman from news coverage and called the police. After a brief stand-off, the men were captured and returned to Winnipeg.

The arresting officers (source)

Leishman was then held at the Vaughan Street Jail to await trial on an even longer list of charges.

He was held in an empty wing and had access to the corridor outside his cell. On October 30, 1966Liehsman managed to pick the lock at the end of the hall, 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 street and Jefferson Avenue. 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, Leishman plead guilty to all nine charges against him. He received a total 15 year sentence, seven for the gold heist and escapes plus the remaining eight years left on his Toronto sentence.

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 jail time was made up of 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, the Leishman family moved to Red Lake, Ontario where Ken took a job as a bush pilot and opened a tourist shop. They also became devout Mormons.

The couple were, by all accounts, well liked by community members and Ken even served as the chair of the local Chamber of Commerce.

On December 14, 1979, Leishman was performing a medi-vac 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 read posts showing that there is still a great deal of interest in Leishman and his antics.


I wasn't around at that time, so I can only guess that being an "everyday man", (a kitchenware salesman from North Kildonan with a wife and kids), pulling off relatively victim-less crimes worthy of a Hollywood film was a huge factor.

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 his demeanor appears not to be something just for the cameras. 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.

Anonymous 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.

Anonymous 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.

Anonymous said...

This is so interesting . If I recall correctly I went to school with his son Trent. They owned what I thought was called the Trading Post in Red Lake at the time also. They were all a very nice family. I was a teenager than , not sure about the political end of it. Wonder what happened to the rest of the family. This was a great read . Brings back memories.

Anonymous said...

Interesting to read these stories and connections of my grandpa Leishman whom I never met.

Allicity said...

Nice information...Thanks for sharing such a lovely post.
Family law is a complex field, and it can be particularly daunting for clients when emotions and personal relationships are involved.
Best Family lawyer winnipeg

Winnipeg said...

Amazing post..nice information.Keep sharing on more.
McJannet Rich, our lawyers have decades of professional experience in the Manitoba legal system. Our Winnipeg practice covers a wide range of fields, and we always fight to achieve the best possible resolutions for our clients’ cases.
Employment lawyer Winnipeg

Anonymous said...

My mom was a young war bride from London England in 1946. My dad was from Treherne.Ken was a young man who took a fancy to my mom and followed her around town offering to carry her groceries.. My mom used to say he was quite the charmer.. We had a good chuckle when he had been picked up at Jefferson and Main, since we lived on Jefferson, we would tease my mom that Ken was coming to see her

Jay Tiwari said...

Looking for taxi to halifax airport? Deeplink Taxi provides reliable taxi and limo services to get you anywhere safely. We also provide Airport Taxi from Halifax airport at economical rates. Call us now.