He spent the first eleven years of his life on his family's farm in Charlottetown, where he began his work with horses.
[1] Due to his family's economic circumstances, Wilson had to stop attending school after eight grade to take a job as a messenger boy at the Frost Forwarding Company.
Three years later, Wilson joined the A. Towle Company, a larger competitor of Frost Forwarding, as an equal partner.
[3] On January 12, 1921, Wilson was elected president of the Short Ship Circuit, a harness racing chain.
[5] In 1932 Wilson played an instrumental role in bringing the Grand Circuit back to Rockingham Park.
He served as manager of the meet, which was sponsored by the Boston Garden Corporation in connection with its New England States Fair.
He was asked to stay on as chairman of the board, but declined because he wanted to cut down on his business and racing responsibilities.