NHL history: Worst trade in each team’s history: Montreal Canadiens
There are some trades on this list that are just plain easy. This is one of them. This might be the worst trade in NHL history. The Montreal Canadiens were forced to choose between their franchise goalie and their head coach. They picked the head coach, and after that coach left Patrick Roy in to allow nine goals against, embarrassing him in the process. Roy would never play another game for the Canadiens again, and the team eventually traded him to the Colorado Avalanche.
Montreal hasn’t won anything since that day. Roy was in the net for Canada’s last Stanley Cup win. He actually went on to win the Stanley Cup the season he was dealt. It was his first of two Cups in Colorado, as he also led the Avs to a championship in 2001.
Meanwhile, the Canadiens took what they could get. What they could get was not much. Andrei Kovalenko didn’t make it past this season with the Canadiens. He was on the Edmonton Oilers the next season. Martin Rucinsky played seven seasons with the Canadiens. He was a hard-nosed player who was in the penalty box a lot. It’s not exactly what you want for Patrick Roy. Jocelyn Thibault was the replacement in the net, and that just wasn’t fair to him. He was gone in a few years.
Oh, and on top of Roy, the Canadiens traded away their captain Mike Keane. This trade somehow gets worse! He brought a certain leadership quality that helped in the playoffs.