Leonard Patrick "Red" Kelly was a Canadian professional hockey player and coach. He was also a Liberal Member of Parliament for the Toronto-area riding of York West from 1962 to 1965, during which time he also won the Stanley Cup—twice—while actively playing for the Toronto Maple Leafs. Kelly played on more Stanley Cup-winning teams (eight) than any other player who never played for the Montreal Canadiens; Henri Richard (11), Jean Beliveau (10), Yvan Cournoyer (10) and Claude Provost (9) won their Cups with the Canadiens. He was also one of the only two players to have never played for the Canadiens and to be part of two of the nine dynasties recognized by the National Hockey League (NHL) in its history. In 2017, Kelly was named one of the '100 Greatest NHL Players' in history.

John James "Jolly Jack" Adams was a Canadian professional ice hockey player, coach and general manager in the National Hockey League and Pacific Coast Hockey Association. He played for the Toronto Arenas, Vancouver Millionaires, Toronto St. Patricks and Ottawa Senators between 1917 and 1927. He won the Stanley Cup twice as a player, with Toronto in 1918 and Ottawa in 1927, and was inducted into the Hockey Hall of Fame.