Player and coach together : Henry Richard, of the Montréal Canadiens, won the cup 11 times. Hector "toe" Blake won the cup 2 times as a player of the Montréal Canadiens and 8 times as a coach of the Montréal Canadiens for a total of 10 cups. Next, there is Jean Beliveau and Yvan Cournoyer who won the cup 10 times. As a coach, Scotty Bowman has won it nine times.
Montreal Canadians with 24 Stanley cups
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 won 6 Stanley Cups in a career that only spanned 8 years.