 McCann was hired by E. P. Taylor as head trainer at Windfields Farm in 1950 where he would spend the next twenty-one years.During his training career, McCann conditioned seven Canadian Hall of Fame horses and six horses that won Canadian Horse of the Year honours including Canadian Triple Crown winners New Providence in 1959 and Canebora in 1963.He also trained six winners of Canada's most prestigious race, the Queen's Plate and overall won seventeen races that now comprise the Canadian Classics.