The player with the most championships is Henri Richard who won 11 Cups with the Montreal Canadiens.
Heneri Richard (The Pocket Rocket) with 11
The Montreal Canadiens have 24 NHL titles.
Wayne Gretzky has won the NHL MVP award (Hart Memorial Trophy) a record nine times during his career, eight consecutively.
The Montreal Canadians
Montreal Canadiens (24)
The Montreal Canadiens won the most championships in the NHL.
Yogi Berra won the most World Series championships as a player with 10.
The player with the most NHL championships is Henri Richard. He won the Cup 11 times with the Montreal Canadiens, matching Hector (Toe) Blake who won 3 Cups as a player and 8 as coach of the Montreal Canadiens. Only Scotty Bowman has more Stanley Cup championships as a coach with nine.
This year, both the Pittsburgh Steelers (NFL) and the Pittsburgh Penguins (NHL) won their championships. It was the first time both an NFL and an NHL team won from the same city.
Bill Russell- 11 championships
Joe DiMaggio has the most, that I know of. He won 9 with the New York Yankees.
Sam Jones (Boston) 10