Legend – Jockey

During an era when thoroughbreds were often trained and ridden by the same man, Dick O’Leary was considered without equal. Born in Port Credit, Ont., O’Leary earned the nickname “Tricky Dick” because of his skillful and clever handling of horses during the 1870s and 1880s. Often described as “cagey” and “crafty”, he was acclaimed as Canada’s greatest jockey and was the first to ride three Plate winners – Fearnaught in 1872, Bonnie Bird in 1880 and Colonist in 1889.

O’Leary was so sure of winning the Queen’s Plate in 1888 that he put his young son Charlie on the back of the winner – Harry Cooper. It marked the only time in Plate history a father-son combination had scored in Canada’s oldest stakes race.

The following year he was back in the saddle of Plate winner Colonist, Toronto newspaper The World said he was the oldest jockey active in America. “He’s in the neighbourhood of fifty-five and as to his skill in the saddle, though probably not what is was a few years ago, he’s still an excellent judge of pace. As a trainer, however, it is an undeniable fact that he has no equal in Canada.”

O’Leary was also the first trainer to saddle four Plate winners – Fearnaught, King George, Harry Cooper and Colonist. O’Leary often skipped school classes in Port so that he could hang around the horses at the old Carleton course in West Toronto. At age 14 he ran away from home and was smuggled across the border to ride in the U.S.