Henri Richard of the Montreal Canadiens leads with 11 Stanley Cups as a player. Jean Beliveau and Yvan Cournoyer also of Montreal, have 10 cup wins each as players.
Toronto
Henri Richard, with 11
Henri richard with 11 cups
The team with the second most Stanley Cups is the Detroit Red Wings, with 11,although they haven't won a championship since 2008 Detroit Red Wings - Second - 11 cup championships. Toronto Maple Leafs - Third - 11 cup championships.
Red Kelly is the most successful NHL player who never played for Montreal. He won 8 Stanley Cups with Detroit and Toronto between 1950 and 1967.
The Montreal Canadians with 24 Cups. The team in second place is Toronto Maple Leafs with 13 Cups.
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
Henri Richard with Montreal canadiens - 11 times
The Canadians
Scotty Bowman
Henri Richard won eleven (11) Stanley Cup championships playing as a member of the Montreal Canadiens.
Not even close Montreal tops the list and then Toronto is a distant second after that everyone else is not even close, Detroit is the American team that has the most Cups I believe.