Prime minister John Diefenbaker was a very good friend who visited Leonard in the hospital and wrote the eulogy at his funeral.
He worked as a merchant and technician, and served in the Royal Canadian Air Force from 1940 to 1946, spending three and a half years overseas and reaching the rank of Flight Lieutenant.
In the 1960s he owned and operated a hardware store on Sherbrook Street in Winnipeg with his supportive wife Sarah (Sadie) and three young children; Marilyn, Robert and Anne Claydon.
The Claydon Hardware Store sold the first black and white televisions to Winnipeggers and stocked an assortment of appliances, toolkits of hammers, nails and radios.
Leonard helped find an apartment that accepted a guide dog for a blind tenant and woman who was Deaf in search for a job and lodgings.