Scotty Bowman
23
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
The Canadians
Bowman won 9 Stanley Cups between 1973 and 2002 as head coach of the Montreal Canadiens (1973, 1976, 1977, 1978, 1979), Pittsburgh Penguins (1992), and Detroit Red Wings (1997, 1998, 2002). He also was a front office member when the Penguins (1991), Red Wings (2008), and Chicago Blackhawks (2010) won Stanley Cups.
ken dryden -6
ken dryden
Canadiens
Montreal Canadians with 24
Toronto
The Montreal Canadiens have won 24, which is the most by far.
No, the Montreal Canadiens have won the most Stanley Cups.
Montreal Canadien won this and most Stanley cups.