When you think of the worst trades in Montreal Canadiens history, one sticks out like a sore thumb. The situation was avoidable from the start, and the players brought in only made matters worse. The Patrick Roy trade stands alone as the worst trade in Canadiens history.
To get a better picture of why the trade happened, you need to go back to the start of the 1995-96 season. The Canadiens fired Jacques Demers four games into the season and hired Mario Tremblay as his replacement. Roy and Tremblay were former teammates, but did not have the best of relationships. Tremblay would regularly mock Roy and was very critical of him on his radio show.
The tension was already high between the two, and it only got worse 24 games into the 1995-96 season. During a game against the Detroit Red Wings, Roy was not at his best. He gave up five goals in the first period, and instead of pulling him from the game, Tremblay chose to keep him in. Tremblay finally pulled Roy after he let in the ninth goal as the Canadiens lost 11-1. Roy immediately walked past Tremblay and went to talk to team President Ronald Corey, and told him, "It's my last game in Montreal." Roy felt like Tremblay left him in the game to humiliate him in front of the Canadiens' fans.
Four days after the game against Detroit, Roy was traded, alongside captain Mike Keane, to the Colorado Avalanche for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko. The trade was perceived as one-sided at the time, and hindsight has only confirmed it.
For the Canadiens, the centrepiece of the trade was Thibault, who was coming in to replace Roy as the starting goalie. He spent parts of four seasons in Montreal before being moved to the Chicago Blackhawks. In his time in Montreal, he was fighting a losing battle. Coming in to replace the best goalie in the league is a tough act to follow. He showed flashes that he could be a good goalie early on, but that quickly faded. In 158 games in a Canadiens sweater, Thibault has a 2.73 goals-against average and a .908 save percentage.
Arguably, the best player the Canadiens acquired in the trade was Rucinsky. He spent parts of seven seasons in Montreal, and in 432 games, he had 134 goals and 297 points. He was good early on, scoring 60 points in his first season with the Canadiens in 56 games. He followed that up with two 50-point seasons before the production started to fall off. The final piece of the trade, Kovalenko, spent one season in Montreal before being traded in the offseason to the Edmonton Oilers.
For the Avalanche, this was a big move for the franchise, which had just relocated from Quebec City. In Keane, they acquired a veteran leader, but a player whose production was on the decline. He spent two seasons in Colorado, playing 136 games, recording 20 and 47 points before leaving in free agency to sign with the New York Rangers.
Now, let us get to the main asset in the trade. Roy was not spectacular in his first regular season with the Avalanche, posting a 2.68 goals-against average and a .909 save percentage, but that all changed in the playoffs. He was a monster in the playoffs as the Avalanche won the Stanley Cup in their first season in Colorado. He spent the rest of his career with the Avalanche, winning another Stanley Cup in 2001, where he took home the Conn Smythe Trophy. Roy played 478 games with Colorado, posting a 2.27 goals-against average and a .918 save percentage, on his way to becoming a legend in the city, getting his 33 jersey retired in 2003.
Roy made the Canadiens regret the trade from the very start, helping the Avalanche to two Stanley Cup victories, while the Canadiens are still searching for their first one since 1993. The Canadiens fans may have turned against him for a little bit, but he could not really hear them with his two extra Stanley Cup rings, "plugging his ears." It will always be remembered as the worst trade in Canadiens history.