He began playing organized baseball in Canada and Michigan and played one season of Major League Baseball as an infielder for the Indianapolis Hoosiers in 1884. He was a manager of five major league clubs and several minor league clubs, including stints with the Indianapolis Hoosiers (1884–85), Detroit Wolverines (1885–1888), Kansas City Cowboys (1888–89), St. Louis Browns (1893) and Pittsburgh Pirates (1898–99). He led the 1887 Detroit Wolverines to the first professional sports championship for Detroit with a National League pennant and a victory over the St. Louis Browns in the 1887 World Series. He was also the business manager of the 1914 Indianapolis Hoosiers team that won the Federal League pennant, the first and only major league baseball championship for Indianapolis.\n', '

Watkins was born in Brantford, Ontario, Canada, in 1858. His parents, John Harton Watkins and Eliza Jane (Tyler) Watkins, were immigrants to Canada from Wales and Ireland, respectively. His mother died in 1868, and he was thereafter raised by his maternal grandparents in Erin, Ontario. Watkins attended Upper Canada College in Toronto for one year, and he began playing organized baseball in 1876 as part of "the academy team" in Milton, Ontario, a suburb of Toronto. He also held jobs as an apprentice for a manufacturer of novelty games and with a branch of the Ingles Corliss Engine Works. In 1879, at age 21, Watkins moved to Port Huron, Michigan, where he lived for the next 40 years.\n', '

From 1879 to 1880, Watkins played for the Maple Leafs of Guelph in Southwestern Ontario. The Maple Leafs won the Canadian amateur championship while Watkins was a player. In 1881 and/or 1882, he was a player-manager for the Atlantic Club of St. Thomas, Ontario (part of the London, Ontario metropolitan area). He led the Athletics to the Ontario provincial baseball championship in 1881.\n', '

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