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.
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
The Canadians
Scotty Bowman
Sidney Crosby
ken dryden
Canadiens
ken dryden -6
Montreal Canadians with 24
Toronto
The Montreal Canadiens have won 24, which is the most by far.
Montreal Canadien won this and most Stanley cups.
No, the Montreal Canadiens have won the most Stanley Cups.