Jean Beliveau has won 17 Stanley Cups. (10 as player, 7 as executive)
Henri Richard has won 11 Stanley Cups, all as a player.
The Montreal Canadiens have won the most Stanley Cups with 24.
The Montreal Canadiens have won the most Stanley Cups, as of 2014.
Mike Gartner, Luke Richardson and Harry Howell played well over 1400 games without winning a Cup. Many have played over 1000 games without winning. However, these guys at least made the playoffs once in a while. The most unusual is probably Guy Charron who played 734 regular season games with Montreal, Kansas City, Detroit and Washington and not only never won a Cup but never once made the playoffs.
it is Toronto with 13 Stanley cups
Manny Ramirez has the most postseason games played as a non-member of the Yankees. He played in 111 games.
Wayne Primeau who has played 90 games in the playoffs but has won no Stanley Cups. Miikka Kiprusoff and Jarome Iginla have both played 47 playoff games for the Flames.
Red Kelly is the most successful NHL player who never played for Montreal. He won 8 Stanley Cups with Detroit and Toronto between 1950 and 1967.
Most recently, in the 2013 Stanley Cup Playoffs, the Chicago Blackhawks won the Stanley Cup, beating the Boston Bruins in 6 games.
The first year the Chicago Blachawks won the Stanley Cup, they beat the Detriot Red Wings. They won three out of the four games they played. Four years they won the Stanley Cup again, in 1938, they were able to beat the Toronto Maple Leafs, by winning three out of the four they played. Then next time they won the Cup was in 1961, when they beat the Detriot Red Wings, by winning 4 out of they six games they played. The third time the hawks took the cup was in 2010. They played the Philadelphia Flyer and beat them by winning four of the six games they played. The most recent Stanley Cup they won was in 2013, when the Hawks took the victory over Boston Bruins in a four to two game series.
the Detroit Red Wings