The Montreal Canadiens with 24 (23 during the NHL era, and 1 win predates the NHL) are the winningest team in the NHL. The second most have been won by the Toronto Maple Leafs with 13, although they have not won since 1967.....
The Montreal Canadiens won the most championships in the NHL.
Montreal Canadiens
Chicago blackhawks
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.
Bill Russell
Wayne Gretzky
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
Phil Jackson
Joe DiMaggio has the most, that I know of. He won 9 with the New York Yankees.
Sam Jones (Boston) 10