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”. Between the late 50s and 60s he committed a number of crimes including bank robberies, stealing planes and escaping custody. His piĆ©ce de resistance was 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 seen as a dangerous 'public enemy', the North Kildonan metalware salesman and father of seven, charmed Winnipeggers and gained a sort of “folk hero” status to millions of Canadians due to his smile, suave demeanor and snappy dressing !

Leishman was born in Holland, Manitoba on July 20, 1931, the oldest of three children.

In 1938 his parents separated and Mrs. Leishman took a job keeping house for a widower. The man and seven year-old Ken did not get along and he was physically abused. Mrs. Leishman was given an ultimatum: to keep her job and place to live, (hard to come by in rural Manitoba during the Depression), Ken had to go. So he did and he ended up in seven foster homes in one year, finally ending up 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 his grandparents' farm. There, he got 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 and work with him in Winnipeg. Things did not go well and soon 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 ended with a burst appendix, a CNR yard job ended after being struck by a boxcar, (he spent three days in a coma).

At age eighteen he seemed to be getting things together. 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 and as a salesman for a cookware company.

Even though he was earning a decent income, the plane, the nice home in River Heights and now children were hard to support given Ken's love for nice clothes and living a good life.
That's when big-time crime entered the picture.

Though living in Winnipeg, 26 year-old Leishman’s first heist took place in Toronto on December 17, 1957. In what a Canadian Press story from the day called “one of the most daring robberies on record”, he entered a bank and asked to see the bank manager. When introduced, he produced a gun and forced the manager 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 fled back to Winnipeg.

He used the same m.o. in Toronto again in March 1958 but that time a teller pressed the emergency alarm. Leishman was caught on the pavement outside the bank after tripping over a woman.

He plead guilty to the crimes 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 (leaving the province of Manitoba) in 1966. He was picked up by RCMP getting off a commercial flight in Vancouver. On March 11, 1966 the Mounties escorted him back to the city in what a Free Press story (March 12, 1966) called "one of the hushiest hush-hush police operations on record in Winnipeg".

While proceedings to have Leishman returned to Stony 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 some years. He knew that regular 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 4 accomplices Leishman's plan involved the impersonation of Air Canada employees complete with home-made ground crew uniforms and a stolen Air Canada van. They 'intercepted' the 12 bars of gold right on the tarmac.

The crime may have been easy but the aftermath, not so much. The abandoned Air Canada van was found soon after the incident and the police were zeroing in on a couple of suspects.
One of them named Leishman as the mastermind behind the heist. The blizzard of 1966 hit right after the heist making the transportation and hiding of the gold bars nearly impossible.

By the time Leishman was arrested in B.C. the police already had the 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 do road blocks at their communities. The RCMP called in every on and off-duty officer and to man 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.

He was caught almost four hours later at a phone booth at Main and Jefferson. The next day, jail administrators had experts going 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 in which he used a strip of cloth and piece of wire).

On November 1, 1966 a surprise announcement was made. Leishman was pleading guilty to all nine charges against him. He received a total fourteen year sentence. Eight for the gold heist and charges relating to his escapes and the remaining six from the original Toronto robbery and parole break.

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 stint was cobbled together from numerous crimes over a number of years, some time was to be served concurrently, some not. Incredibly, the Parole Board ruled that his sentence had been improperly calculated and that he should be immediately released ! It 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.
Winnipeg Free Press, May 7, 1980


I originally posted about Leishman in 2008 or so (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 he being an everyday man, (a cutlery salesman in a modest home in North Kildonan with a wife and kids), pulling off crimes usually seen in 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.

The comments below, and emails that I have had behind the scenes, show that the charm offensive was not something just for the cameras or part of his criminal persona. He remained a well liked and respected man until the end.

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.

News stories:

Ottawa Bound Bullion intercepted at airport - Canadian Press, March 1966
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
- Account of the Flying Bandit - Roland Penner (a lawyer representing an accomplice of Leishman).


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.

Muhammad Amjad said...

That is so interesting.....and cool.This has turned out to be an amazing night.

Hotel furniture

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.