Kenora Thistles
Donated in 1892 by Lord Stanley of Preston, the Governor General of Canada, the Stanley Cup was originally awarded to the top amateur team in Canada, who would then accept challenges from the winners of other leagues. From its inception until 1912, the Cup was nearly always won by teams from Montreal, Winnipeg, and Ottawa. In 1903 Ottawa won the Cup, after finishing the season tied for first in the Canadian Amateur Hockey League with the Montreal Victorias. They played a two-game, total-goal series for the league championship. The Montreal Hockey Club, who had held the Cup, finished third in the league and therefore lost the right to keep it.
Cully Wilson
Wilson began his professional career with the National Hockey Association's Toronto Blueshirts in 1912. The next year, he won his first Stanley Cup when the Blueshirts beat the Montreal Canadiens. He was a part of the "first" expansion of professional hockey when the Pacific Coast Hockey Association agreed to compete with the NHA in an east-west rivalry for the Stanley Cup championship. As a member of the Seattle Metropolitans, Wilson won the Stanley Cup for a second time in 1917, again beating the Montreal Canadiens.