Ten Infamous and Notorious Canadian Bank Robbers

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Canada is overall a safe country to live in with the crime rate being not as high as in other countries or parts of the world. When researching for this article I could not believe how hard it was next to other countries to locate famous bank robbers but after hours of searching, I did manage to find 10 of the most infamous bank robbers in Canadian history. If you enjoy history then this little piece should be entertaining. Enjoy!

Stephen Reid

Stephen Reid got his infamous bank robber title after him and his crew known as the “Stop Watch Gang”, robbed over 100 banks across Canada and the United States.

Reid was born in Massey, Ontario on March 12, 1950. At the young age of 16 he turned to criminal activities, which eventually lead to his arrest and incarceration at age 21, after he took part in a theft of gold bars in Ottawa, Ontario. It was in the late 70’s when Reid manages to escape from prison along with Patrick Mitchell, Lionel Wright and that is when the famous “Stop Watch Gang” was formed.

During the gang’s bank robbing sprees, it is said that they had stolen at least $15 million Canadian between the 70’s and early 80’s. FBI finally caught up with Reid in 1980 and he was sentenced to serve time in the “Marion Pen” in Illinois until his extradition to Canada. After serving sometime in Canada, he was paroled in 1987 and a year later went on to publish his book “Jack Rabbit Parole”, and then got married and had two daughters and moved to Vancouver, Island.

Life seemed to have turned around for Reid but in 1999, while high on cocaine and heroin and struggling with addiction he again attempted to rob another bank but was caught very quickly. This time Reid was sentenced to 18 years in a British Columbia jail.

Last I heard Reid was released on a day parole in January 2008.

Edwin Alonzo Boyd

Boyd is known for starting the infamous Canadian “Boyd Gang” in the late 40’s which pulled off a string of bank robberies across Ontario, Canada.

Boyd was born in Toronto, Ontario on April 2, 1914 and was the eldest son to a police officer. During the depression on the 1930’s he had minor scrapes with the law but nothing really serious. Boyd then went on to join the Canadian Army in WWII, but when he returned he couldn’t find steady work and once again turned to crime.

One afternoon, Boyd was reading the local newspaper article on how a kid the day before robbed a bank with no gun and got away with it. This got him thinking and soon after Boyd had a plan of his own. He went to his closet and pulled out a pistol which he brought home from the war and got a disguise. He then went to a bank and successful robbed it which started the next series of events. Sometime in the 40’s Boyd had been caught and was serving time in jail when on November 4, 1951 him, Lennie Jackson and Willie Jackson all escaped from jail and met up with getaway driver Valent Lesso and formed the “Stop Watch Gang”. Within months of their escape the gang had pulled off a string of daring robberies including the biggest robbery in Toronto’s history. About a year later Lennie and Valent where pulled over on March 6, 1952 by a detective when a gun fight broke out and the officer was shoot dead. A short time later Lennie and Valent where both caught after being injured in a shootout with police and Boyd was later tracked down.

Then on September 8, 1952 Boyd, Lennie and Valent and escaped once again and became the subjects of Canada’s largest manhunt in history but only after 10 days 2 of the men were captured and Boyd was caught 8 days after that. Boyd received 8 life sentences with a possible of parole and Lennie and Valent were hung on December 16, 1952 back to back for the death of the Toronto police detective.

In 1966 Boyd was paroled and soon moved to British Columbia where he married a disabled woman whom he cared for the next 35 years, till they were both placed in a home for seniors. Edwin Alonzo Boyd died May 17, 2002 at the age of 88.

Ken Leishman

Ken Leishman is known in Canadian history for pulling the biggest gold heist Canada has ever seen.

I couldn’t find much on the history of Ken but what I did find was interesting. It turns out that he was a polite bank robber who never used a gun and who made a series of daring getaways using stolen airplanes he had hot wired, earning him the name the “Flying Bandit”.  He is best known for his March 1, 1966 heist of gold bars from Winnipeg National Airport. He forged some documents and him and his crew went to the airport and simply picked up the $400,000 in gold and drove off.

Ken was caught a short time later but the all the gold except 1 bar had not been recovered. He was released from jail in 1977 and went on to be the President of the “Red Lakes” Chamber of Commerce in 1978. As far as I know he is still alive somewhere.

Monica Proietti

Monica Proietti is probably best known as “Machine Gun Molly”, a ruthless female gangster from the 50’s and 60’s.

Molly was born February 25, 1940 in Montreal, Quebec to a poor immigrant family, many of whom were involved in crime at someway. At the very young age of 13, Molly had become a prostitute to help support her family while her grandmother ran a school of crime for the neighborhood children. In 1956 at age 17, she had married Anthony Smith who was 33 and an Irish gangster and the couple had 2 children. By 1961, Smith had been deported from Canada for crimes he committed here and again Molly was on her own. She soon started to date another gangster named “Viateur Tessier” but after a short romance he was caught for a pervious bank robbery and received 15 years.

Molly then went on to become a getaway driver for a group of bank robbers but eventually ended up running the gang in the end. It was finally on September 19, 1967 when police had caught up with Molly and after a vicious gun fight and high speed car chase; she was shot and killed by police at only age 27.

It was said that Molly was suspected in robbing over 20 banks and got away with over $100,000.

Ivan Grose

Ivan may not be as infamous as the previous robbers you have read about, but none the less he is still famous here for what he went on to do after he served his time for bank robbery.

Ivan was born October 8, 1928 in Toronto, Canada. He never had trouble in school and was an ideal child growing up. From 1947 to 1951 he served in the Royal Canadian Air Force. For some reason in 1957 only 6 years after getting out of the Air Force Ivan then age 29, decided to hold up a bank in Hamilton, Ontario. During the robbery he took a 22 year old male as a hostage while trying to escape with $6,000 but didn’t make it far before authorities captured him.

Because of Ivan’s service in the Air Force and for not being a career criminal, the judge only sentenced him to 19 months in jail which he was a model prisoner for his stay. After being released from prison Ivan was finished with the criminal life and went on to be a pretty successful business man.

Last I heard in 1993, Ivan Grose became the first Liberal MP elected for Oshawa, Ontario in 47 years.

Alvin Karpis

Alvin is another famous Canadian gangster from the 1930’s who is known for his crimes across the United States mainly.

Alvin was born August 10, 1907 in Montreal, Quebec but his parents moved and raised him in Topeka, Kansas. He started his life of crime and the very young age of 10 and by 1924 had been sentenced to 10 years for burglary to a reformatory. In 1931, Alvin was released from prison and soon joined the “Ma Barker” gang which down the road became known as the “Karpis-Barker Gang”. They had become one of the most formidable gangs of the 1930’s and had committed every crime you could think of. Authorities finally caught up with Alvin in 1936 and he was sentenced to life imprisonment at the new “Alcatraz” at the time.

Alvin served about 25 years before he was moved out of the infamous prison that was being shut down, and was moved to finish serving his time in another prison. In 1969, he was paroled and deported back to Canada were he wrote his first book in 1971 and then a second in 1979 which toured across Canada.

Alvin then moved to Spain in 1973 and on August 26, 1979 he was discovered dead in bed. At first it was said that he had committed suicide by taking to many sleeping pills, but shortly after doctors confirmed he had died of old age.

Roger Caron

Roger Caron had spent his whole life in trouble with the law and eventually wrote a series of books describing the series of events.

He was born April 12, 1938 in Cornwall, Ontario and had his first brush with the law at age 12 when he and a gang of children broke into a box car to steal can goods. He got away but later was caught when some of the boys told police who he was when they got caught. Roger then went on with his criminal activities until they eventually landed him in jail. While in prison in 1978, he got his memoir “Go-Boy” published which was about his 23 years of life behind bars and soon after got 2 more books published.

After being released Roger went on to lead a pretty quite life until April 1, 1992 when high on cocaine and shaking from Parkinson’s disease, he robbed a Zellers and tried to escape from police on a public bus but within minutes was captured. While waiting to be sentenced for the Zellers robbery, Roger had made 9 escape attempts. He ended up receiving 9 years and 3 months for his crime and the escape attempts.

While serving the 9 years and 3 months Roger had received, he ended up having 2 heart attacks and later on married a legal secretary. He once again was paroled on December 10, 1998 but less then 3 years later, police acting on a tip arrested Roger with a loaded gun which was against his parole conditions. In February 2004, he received 20 months for possession of a loaded gun and 15 other counts of robbery where dropped due to lack of evidence.

In April 2005 at age 67, Roger Caron was once again released and was considered a “Free Man”. Shortly after getting out of prison, he and his wife moved to Barry’s Bay in Ontario where they live today.

Tyrone William Conn

Tyrone was born to a 15 year old mother who eventually gave him up a short time later when she turned 18.

He was born January 18, 1967 and was raised in Belleville, Ontario by his adoptive parents. Tyrone was eventually given back to the adoption center because he was considered too much trouble and spent most of his young life going from one home to another. It was of no surprise to anyone when he was 16 he robbed his first bank. He was only on the run a short time before being captured by authorities.

In his 16 years as a criminal, Tyrone had spent half his life in prison and between the years 1983 to 1992, had been charged with over 30 different offences. By age 25 he had been sentenced to 47 years in prison and was due to be released in the year 2032, even though he had no prior history of violence.

On May 28th, 1998 Tyrone was transferred to the “Kingston Penitentiary”, one of Canada’s most secure prisons after successfully escaping from 3 other prisons. This jail couldn’t even hold him because on May 6, 1999 Tyrone became known as the only inmate to escape over the wall in the last half century. 12 days later on May 12, 1999 after robbing and escaping another bank robbery, police caught up with Tyrone in a basement apartment where he barricaded himself and had a standoff with police.

During the 90 minute standoff with police, Tyrone was in constant contact with CBC producer Theresa Burke on the phone. After 90 minutes and entering the apartment, police announced that Tyrone Conn had died of a self inflicted gun shot wound to the head.

Bill Miner

Bill Miner is not a bank robber but actually Canada’s first train robber.

Miner was born in 1847 in Bowling Green, KY and was never actually a Canadian resident but most of his crimes where committed in Canada. At age 19 he was sent to “San Quentin” prison for his part in a robbery. He became known as Canada’s first train robber on September 10, 1904 when he robbed a train of its gold dust contents worth $6,000 dollars at the time.

Miner was not a very smart criminal and it showed when he tried to rob 2 different train shipments of gold dust and failed. First train was the “Canadian Pacific Railway Transcontinental Express No.1” which didn’t go as plan. Him and a few other guys ended up using too much TNT when trying to blow open the door to the train car which contained the money, they ended up blowing the box car totally away. The second train was the “Canadian Pacific Railway Imperial Limited” which was also a total failure. After getting aboard the train, Miner and the crew had not been able to locate the box car with the money and gold dust in it so they stole liver pills.  

On September 2, 1913 at age 70, Bill Miner had died of liver disease but had robbed over 30 trains and stage coaches and escaped prison 10 times through out his life. He was also known as the “Grey Fox” or “The Gentleman Bandit” because he never used violence during his crimes.

Through out the years there have been many movies, books and re-enactments made of Bill Miners life and criminal career which makes him infamous in my eyes.

John Hamilton

Little is known about this mysterious mans early life, until about the 1920’s when he started his criminal career. None of his crimes where actually committed in Canada but he is still widely known across this country because he was born here somewhere.

Hamilton’s criminal career started off when he rob a gas station in St. Joseph, Indiana and got caught a few days later. He was sentence to 25 years in prison and while incarcerated, Hamilton met fellow bank robbers Russell Clark, Charles Makley, Harry Pierpont, Homer Van Meter and the soon to be infamous John Dillinger. On September 26, 1933 a total of 10 men including Hamilton escaped and eventually went on to meet up with John Dillinger after the gang broke him out of prison.

Hamilton and the gang went on a huge crime spree in1933 that lasted to 1934 when finally John Hamilton was ranked number 3 on Indiana’s list of public enemies. On April 23, 1934 Hamilton was fatality wounded after a shootout with police and never received medical attention for the wound. He would later die on April 30th 1934.

John Dillinger and another member of the gang buried Hamilton’s body after trying to remove his face and finger prints with a type of acid called “LYN”. On August 28, 1935 authorities located the body and compared its teeth to prison dental records belonging to Hamilton and it concluded that it was the body of famous gangster John Hamilton.


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