Scotty Bowman

Regarded as one of the greatest coaches in the history of sports, Scotty Bowman has won the Stanley Cup 13 times throughout his legendary career.  9 of those Cups have comes with him in the role of head coach. 5 of those Cups came when he was head coach of the Montreal Canadiens in the 1970s, one as head coach of the Pittsburgh Penguins in 1992, and three as head coach of the Detroit Red Wings championship teams in 1997, 1998 and 2002.  In addition Bowman won the Stanley Cup with the 1991 Pittsburgh Penguins as Director of Player Development, the 2008 Detroit Red Wings as a consultant, and in 2010 and 2013 in his current job as Senior Adviser of Hockey Operations with the Chicago Blackhawks.  He also served as head coach and General Manager of the Buffalo Sabres in the 1980s.  Bowman got his first NHL coaching job with the expansion St. Louis Blues.  He led the Blues to the Stanley Cup Finals in each of their first three seasons.  Although they never won the cup, this put Bowman on the radar of the Montreal Canadiens, and the rest is history.