The Montreal Canadiens have had a legendary history in the NHL. However, with all the successes, came some heartbreaking losses and questionable moves from the front office. We often look at all the positives with the Canadiens organization, but let's take a different approach as we near the trade deadline. Let's look at five of the worst trades in team history.
5. Rejean Houle's teardown continues with Pierre Turgeon trade
A Rejean Houle trade highlights this list, but he continued the tear down through the mid-1990s when he traded Pierre Turgeon to the St. Louis Blues. The Canadiens also traded Craig Conroy and Cory Fitzpatrick, acquiring Shayne Corson, Murray Baron, and a fifth-round pick. Turgeon was the Canadiens' best player the previous season, recording 96 points.
Turgeon would play five seasons in St. Louis, finishing off the five years by averaging over a point-per-game. Corson wouldn't be the same player in his second stint with the Habs, and Baron played just 60 lacklustre games.
4. Canadiens acquire Denis Savard for Chris Chelios
Mike Keenan had fallen out with Denis Savard after he took over the Chicago Blackhawks and was looking to change the identity of the failing team. Chris Chelios looked like the perfect addition to the team, and Keenan knew he could get Serge Savard to bite on a deal to acquire the Quebec-native. What Serge didn't account for was that Denis wasn't the same player as when the Canadiens passed on him in the 1980 draft, and Chelios would play another 19 seasons.
Chelios actually outperformed Savard with two 70+ points in Chicago, which were better seasons than Savard ever managed in Montreal.
3. Rod Langway and Doug Jarvis is a forgotten deal
Rod Langway and Doug Jarvis became individual award winners after they lef the Canadiens. Montreal traded Langway, Jarvis, Brian Engblom, and Craig Laughlin to the Washington Capitals for Ryan Walter and Rick Green. Walter and Green were high draft picks, but they didn't become the producers people thought they would be in Montreal. Walter did play a role in the 1987 Stanley Cup win, but Langway and Jarvis had some bigger individual seasons.
Langway was Washington's star shutdown defenseman for the next 11 seasons. He won two Norris Trophies, while Jarvis was also a reliable shutdown forward for the Capitals and won the Selke Trophy in 1984.
2. Ryan McDonagh heads to Broadway
It looked like the Canadiens initially won the trade when they traded Ryan McDonagh, their 12th overall pick in the 2007 draft. Mnotreal also traded Chris Higgins, Pavel Valentenko, and Doug Janik for Scott Gomez, Tom Pyatt, and Mike Busto. Gomez had a massive five year, $7.357 million per year deal, which he would never fully live up to.
Gomez had one good season in Montreal, his first, but his play dropped off significantly over the next two seasons, ending in 11 points in 36 games in 2011-12. McDonagh went on to become the Rangers captain for four seasons, then went to the Tampa Bay Lightning and won two Stanley Cups, including in 2021 against the team that drafted him.
1. Patrick Roy goes to Colorado
It was a quick end to Patrick Roy's legendary tenure with the Canadiens. A 9-1 score against the Detroit Red Wings prompted the incident, which led to Roy's departure to the Colorado Avalanche. It was a near-impossible mission to get subsequent value for Roy. Still, the Canadiens tried to do it by dealing Roy and captain Mike Keane for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko.
Roy led the Avalanche to their first Stanley Cup, then won a second in 2001. He spent seven and a half years in Colorado and was arguably the league's best goaltender all of those years. Rucinsky was a valuable return, but Thibault was average for four seasons and Kovalenko played just 51 games.