This Irish-born athlete immigrated to Canada when he was five, living in Hamilton (Ontario, Canada). In 1902, his sprinting wins qualified him for the 1904 St. Louis (Missouri, United States of America) Olympic Games, an event to which he had to pay his own way. Entered in the 60m, the 100m, and the 200m, Bobby failed to qualify for any of the finals – but took the opportunity to gain valuable experience that helped him dominate the Canadian sprints for the next few years – and earned him selection to the Canadian team for the 1908 Olympic Games in London (England). Leveraging his athletic abilities and experience from the 1904 Games, Bobby took the bronze medal in the 100m in a time 11.0 and the gold in the 200m in a time of 22.6.

Bobby went on to run internationally representing Ireland and Canada until 1912, when he retired from the sport. During his sprinting career, Bobby amassed an extraordinary 400 titles in races ranging from 50m through 440 yards and set six Canadian records along the way.

Bobby gave back to his sport, becoming an official; serving as the captain/manager of the 1928 Olympic Games in Amsterdam (Netherlands) and the 1932 Olympic Games in Los Angeles (California, United States of America); and holding the title of President of the Hamilton Olympic Club. Bobby also took on the role of meet director, an executive with the Canadian Olympic Association and the Canadian AAU – and was a key organizer for the 1930 British Empire Games (now the Commonwealth Games) that were held in Hamilton (1930).

An Irish champion, a Canadian champion, and an Olympic champion, Bobby is a member of the Canadian Sports Hall of Fame (1955) and the Canadian Olympic Hall of Fame (1949).