Coming from a troubled home, he dropped out of school before graduating, and worked various jobs before marrying Elva Shields at the age of 17.

Sometime in the summer of 1951, Leishman started working as a travelling mechanic for Machine Industries, repairing straw cutters in southern Manitoba.

At some point in the next five years, Machine Industries closed its doors, and Leishman started working for Queen Anne Cookware.

[4] On December 17, 1957, Leishman, by posing as a friend of the manager, robbed the Toronto-Dominion Bank on the corner of Yonge Street and Albert in Toronto, Ontario.

Three months later, on March 16, 1958, Leishman attempted to rob the CIBC bank on the corner of Yonge Street and Bloor, in Toronto.

On his most famous robbery, Leishman and four accomplices stole almost $385,000 (just over $3.5 million 2023 dollars) in gold bullion being transported by TransAir to Winnipeg where it would be shipped via Air Canada to Ottawa, Ontario.

Grenkow's brother Paul was recruited to go to Red Lake in the guise of a salesman to watch for a large shipment to leave.

[8] The plan was to leave the gold there overnight, before moving it to a farm in Treherne, belonging to Leishman's uncle, but a blizzard on March 3 and 4 prevented them from recovering it.

Most of the gold bars ended up buried in Backlin's backyard, but were soon unearthed by the local police force who were investigating all of Leishman's suspected associates.

[4] Imprisoned again as a result of the gold heist and awaiting trial, Leishman, assisted by some accomplices, managed to escape from Headingley Jail in September, 1966, and stole an aircraft from Steinbach, Manitoba, reinforcing his reputation as the "Flying Bandit.

[11] With him on the plane was a patient, Eva Harper, who had broken her hip in a snowmobile accident, and medical escort Janet Meekis.

[13] A 2005 television documentary, written by Bob Lower and directed by Norma Bailey, entitled Ken Leishman: The Flying Bandit recounts his life and career as a criminal.