Henri Richard of the montrea canadiens with 11 cups.
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.
I think it was a Mexican who played in five world cups in a row.
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
Scotty Bowman
The Canadians
Canadiens
ken dryden -6
Montreal Canadians with 24
Toronto
ken dryden
The Montreal Canadiens have won 24, which is the most by far.