Montreal Canadiens fans will always tell you that the worst coach in franchise history is the guy doing it right now, whenever "now" may be.
Company man Claude Ruel hated coaching Les Glorieux. He took over a team of veteran stars who had served under Toe Blake, the greatest coach in Montreal history, and had trouble getting them to listen to him, let alone give him respect. He was vilified by his players, the press, and the fans, and earned a reputation as one of Montreal's worst coaches ever. And in two stints as the coach of Les Habitants, he had a winning percentage of .648.
What other sports organization on Earth could call a coach who won a championship and won nearly two-thirds of regular-season games one of the worst in team history? For most organizations, this man would be considered one of the best to ever coach the team.
Unfortunately, Ruel won his single Stanley Cup in 1968-69. It was the end of an era in which Montreal won four cups in five years. This was Toe Blake's team winning a cup; Claude Ruel was just standing in his shoes. The next year, when Montreal missed the playoffs for the first time since 1948, it was Ruel who was blamed.
Al MacNeil was brought in from the Nova Scotia Voyageurs to replace Ruel. He coached the team for a mere 55 regular season games and to one of the most unlikely championships in Montreal Canadiens' history. The experience was so unpleasant for him that he never coached in Montreal again.
The young, monolingual MacNeil was pilloried in the press by the French veterans on the team. Henri Richard particularly complained about his coaching methods and line combinations. Additionally, veteran John Ferguson responded very negatively to being benched for the fast, young Massachusetts born prospect Bobby Sheehan. Al suffered death threats throughout the playoffs and was only vindicated when they won the Stanley Cup.
Neither of these men were the all-time worst coaches of the Canadiens, but at the time the fans, the press and even the players seemed to think so. The standard is higher in Montreal. A highly regarded coach like Pat Burns could be nominated for this list just because he never won a cup in Montreal. Cup winners like Jean Perron and Jacques Demers might make the list because they didn't win enough.
It's a horrible job trying to be the Montreal Canadiens coach and live up to that history and the expectations that come with it. An organization that boasts the likes of Toe Blake, Scotty Bowman and Dick Irvin clearly has a high standard for success.
Special thanks to D'arcy Jenish for his book The Montreal Canadiens 100 Years of Glory and Claude Moutons' The Montreal Canadiens: An Illustrated History of a Hockey Dynasty for detail as well as stories from the eras I didn't live through.