1. Mario Tremblay
Mario Tremblay is best known as the man who forced star goaltender Patrick Roy out of Montreal. He was hired back in 1996, technically replacing Jacques Lemaire, but in reality, he was replacing Jacques Demers. Tremblay was a former Canadiens player who had some issues with Roy. That should have been a huge red flag, but for some reason, the Habs ignored it.
The two didn’t get along and the tension between the two kept rising until it boiled over in December of 1995. Tremblay kept Roy in a game against the Detroit Red Wings even after he allowed eight goals. Eventually, he got pulled after allowing his ninth goal of the evening. But before Roy went into the locker room, he told team president Ronald Corey that he would never play for the Canadiens again.
At this point, the Canadiens had a choice. Either get rid of Tremblay or get rid of their star goalie. They chose the latter and they chose poorly. This trade is how the Canadiens went from winning the Stanley Cup in 1993 to being a shadow of their former selves.
Tremblay had a little bit of success in Montreal during his two-year tenure, but he’ll always be remembered as the guy who made Patrick Roy want to leave the Canadiens.