How should I go about this one?
Option 1: When it comes to Holidays, the one that counts the most is the one with ''the big man'', coming to bring you presents, and in the hockey world, as far as coaches are concerned, there is no one alive bigger than Scotty Bowman, who brought his teams Stanley Cups like Santa Claus fills Christmas stockings.
Or Option 2: Every team needs a head coach, even my all-time Habs Numbers Project team, and what better way than with the winning-est coach of all time, Scotty Bowman?
Either way, I win:
He rarely comes back to his hometown these days, living in the U.S. on a permanent basis for the past 30 years, and most team functions he attends are those of the Detroit Red Wings or, in working duties, the Chicago Blackhawks, with whom he serves as a consultant for GM Stan Bowman, his son.
Like many things related to the Montréal Canadiens of the 1950s-1980s (and again under Bob Gainey's watch in the 2000s), Bowman didn't always have it easy in Montréal. He coached the Habs-affiliated Ottawa Canadiens in the Québec Junior League to a championship, and led the Peterborough Petes to the Memorial Cup, then more championships with the NDG Monarchs and Montréal Junior Canadiens, but still didn't get his first taste of the NHL with the Canadiens, instead starting as an assistant with the St. Louis Blues, but taking over head coaching duties mid-season and leading them to three straight Stanley Cup Finals in his first three seasons at the helm before bowing out in the first round in his fourth season.
Come 1971, he was appointed to coach the Habs, replacing Al MacNeil, who not only didn't speak French but favoured playing anglophones (Frank and Pete Mahovlich over Jean Béliveau, Yvan Cournoyer and Jacques Lemaire up front, Terry Harper over Guy Lapointe, Serge Savard, Jean-Claude Tremblay and Jacques Laperrière on defense, Phil Myre in 30 games in goal despite his statistics being far from Rogatien Vachon's). The farthest thing from a ''player's coach'', Bowman was strict and at times even mean, but apart from teaching someone a lesson / showing them who was boss, he gave the best players the most ice time and was deemed more fair than his predecessor. His goal was to win the Stanley Cup every year, and he would do anything he had to to get there.
On a team that included Guy Lafleur, Steve Shutt, Lapointe, Yvon Lambert and Mario Tremblay among the renowned partiers, the fact that Bowman wouldn't begrudge his players' off-the-rink habits as long as they performed well during games kept the locker room balanced. The coach also had tricks up his sleeve to disrupt the opposition, knowing when to use his tough guys (John Ferguson played under his watch), but also using the city's rabid hockey fanbase and his contacts to have the fire alarm sound off at the hotels where opposing players were staying in the middle of the night, so they'd be tired when it came time to play against the Habs.
And just like it didn't start like a fairy tale for Bowman with a stint in St. Louis before getting the call in Montréal, it ended abruptly when he wasn't offered the general manager's job when his mentor, mastermind Sam Pollock, retired.
The Buffalo Sabres came calling, offering him the dual GM/head coach job. In seven seasons in Buffalo, he held the head coaching job for four full seasons and parts of three others, where he served as interim bench boss after firing whoever he'd appointed when they couldn't do the job.
He stepped down and took some time off from the daily grind of the game, appearing occasionally on CBC's Saturday-night show Hockey Night In Canada for the end of the 1980s, until he became director of player personnel with the Pittsburgh Penguins in 1990, winning the Stanley Cup with the team in that role. However, after the Cup win, head coach Bob Johnson was diagnosed with cancer, and Bowman replaced him behind the bench, leading the team to its second straight Cup.
He left after the 1992-93 season, after the two-time champs and regular-season leaders were ousted in the first round, signing with the Wings, where he coached for 9 years, winning three more Cups in the process while playing in the same conference as the Colorado Avalanche (winners of two themselves), and losing in the Finals to the New Jersey Devils in 1994-95, also known as the Year Hockey Died.
He helped bring the Wings back to respectability, and had the team's old-timers be proud to walk into the Joe Louis Arena every game again. Detroit became an attractive place where superstars could come win a Cup before they retired (Brett Hull, Brendan Shanahan, Luc Robitaille).
By then he had adapted his coaching style, softening it to become a better teacher, communicating more, developing strategies to make use of the NHL's modern landscape, such as having five Russian players - or five Swedes by the end of his tenure - play together and communicate only in their own language on the ice to foil the opposition with tactics they could only see but not hear; he also made the ''left wing lock'' (where the left winger is more of a defensive rover) a common thing to counter the straight-up trap the Lemaire-coached Devils used to kill the game.
He is the NHL's all-time leader in regular-season wins (1244) and postseason wins (222), and counting all Cups at every level, his 13 as a coach and executive rank second only to Jean Béliveau's 17 (10 as a player, 7 as an executive). The way the Hawks are built, he could very well earn a couple more before he decides to step away from the game completely.