3. Alain Vigneault
As I mentioned earlier, the Canadiens have only missed the playoffs in three straight years twice in franchise history (though it’s about to be three unless the NHL comes up with a silly playoff format, which obviously can’t be ruled out). Alain Vigneault was the coach for two full years of the second three-year drought, and 20 games of the third year.
Among all Canadiens coaches who coached at least 100 games, Vigneault has the lowest regular season point percentage at .483%. Also, the Habs only won four of their 10 playoff games with him at the helm, as they got swept in the second round during their lone postseason appearance with him behind the bench.
Vigneault wasn’t a good coach with the Canadiens, but to be fair, he wasn’t quite ready to be a coach. He took the lessons he learned from his failures in Montreal and used them to help him have success with the Vancouver Canucks, New York Rangers, and Philadelphia Flyers. Vigneault took the first two to a Stanley Cup Final, though he lost both. And before the 2019-20 season was put on hold, the Flyers were the most improved team in the NHL.
It took him five years to find another job after the Canadiens fired him in 2001. That’s pretty telling of how bad his time in Montreal went.