Five Worst Montreal Canadiens Trade Deadline Deals Ever

Jan 27, 2024; Philadelphia, Pennsylvania, USA; Philadelphia Flyers former player Mark Recchi speaks
Jan 27, 2024; Philadelphia, Pennsylvania, USA; Philadelphia Flyers former player Mark Recchi speaks / Kyle Ross-USA TODAY Sports
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The Montreal Canadiens are down to the last couple of days before the National Hockey League trade deadline arrives. They are sitting near the bottom of the NHL standings and will surely be looking to sell this week.

That process has already begun as Sean Monahan was sent to the Winnipeg Jets for a first round pick in 2024. There is also a conditional third round pick heading to Montreal in that deal but it only gets transferred if the Jets win the Stanley Cup this season.

Monahan is doing his part to make that happen, as he has scored eight goals in his first 12 games with the Jets and has solidifed their center ice position. They do have a great team and have surged to the top of the Central Division standings so who knows, perhaps that extra pick will end up in the Canadiens hands soon.

What other picks could the Canadiens acquire? They don't have a list of pending free agents that are sure to move, as Tanner Pearson is the only pending unrestricted free agent on the roster. He isn't having a fantastic season, with 11 points in 42 games but is a trusted veteran with Stanley Cup winning experience so he could be on the move.

Even if the Canadiens can land a late round draft pick, they may as well pull off the trade. Adding as many picks at this time of year could lead to a huge payoff down the road, and if the player you are shipping out has his days numbered with your organization you may as well get something for them.

We have seen some of these types of deals work out really well for the Canadiens over the years. Unfortunately, some trade deadline deals have not. Here are the Canadiens five worst trade deadline deals ever.

The Dwight King Trade

The Montreal Canadiens had a strong team in the 2016-17 season. They were on their way to winning a division title in the regular season and knew they were heading into the postseason when the trade deadline arrived that year.

They also knew, or at least ought to have known, what their strengths and weaknesses were. They had the best goaltender on the planet and he was carrying the team to far greater heights than the rest of the roster was going to be able to achieve on their own.

The team did have a pretty solid group of defenders with Andrei Markov, Shea Weber, and Jeff Petry leading the way. Nathan Beaulieu, Alexei Emelin and Jordie Benn added some toughness and grit to the back end, making them a tough group to play against overall.

What the team really lacked was scoring. They had Max Pacioretty scoring at a high level, but that was about it. Alexander Radulov had a good year for them as well but didn't reach the 20 goal mark. Brendan Gallagher didn't have his best season and Alex Galchenyuk was finding his way while Tomas Plekanec was starting to show his age.

So, at the trade deadline, the Canadiens acquired Dwight King for a fourth round pick. They also picked up Steve Ott for an even later pick and Andreas Martinsen for Sven Andrighetto. The trio that was acquired combined to score one goal while Jordie Benn had a pair down the stretch of the season.

It is unfair to just blame King as the worst trade, but he represents the worst, and most head scratching trade deadline we have witnessed from the Canadiens.

The Cristobal Huet Trade

The Montreal Canadiens had one of their most surprising seasons ever in 2007-08. They had missed the playoffs the previous season, by a single point, but were not expected to be a fantastic team all of a sudden.

But then they were. A resurgence from Alex Kovalev as well as breakout offensive performances from players like Tomas Plekanec, Mark Streit and Andrei Kostitsyn all of a sudden made the Canadiens a deep and high scoring team.

They were cruising near the top of the Eastern Conference all season and actually finished first overall in the conference at the end of the season. But, it wasn't because of any trade deadline additions that put them over the top.

In fact, the Canadiens acted like sellers at the deadline in 2008. Though there were rumors suggesting they were in on players like Mats Sundin, Vincent Lecavalier and Marian Hossa, they ultimately... traded away starting goaltender Cristobal Huet.

That was all as they did not acquire a single player during the season via trade. Instead they just moved out Huet who was having a solid season, and would be sensational down the stretch for the Washington Capitals. In return, the Canadiens received a second round draft pick.

They ultimately turned the crease over to 20 year old Carey Price who had a strong rookie season but struggled in the postseason. Obviously his career turned out okay, but he was not ready to carry a team through a playoff grind at that point in his career.

Huet was not a seasoned veteran of dozens of playoff series, but he was in his third consecutive strong season and would have helped the team in the playoffs when Price stumbled. Instead, they landed a second round pick that they flipped a year later to get Mathieu Schneider.

The Vincent Damphousse Trade

The 1998-99 season was one to forget for fans of the Montreal Canadiens. The Stanley Cup winning roster of six years earlier was being picked apart and the team could not look further from contending for another one.

Though they did a pretty good job keeping pucks out of their net, they were among the lowest scoring teams in the league. So, as the trade deadline approached, they decided to sell, sell, sell.

One player they chose to move out was captain, Quebec native, and player that wanted to stick around Montreal for a very long time, Vincent Damphousse. He was not having his best season, but no one around him could score, and Damphousse was 31 years old. So they traded him to the San Jose Sharks while the team was on a plane heading home from their game in San Jose against the Sharks.

The trade initially seemed like a decent one for the Canadiens, as they received first and second round picks for what appeared to be a declining asset. The problem was, Damphousse could still score, he just needed better wingers than Benoit Brunet and Turner Stevenson to make it happen.

He finished that season with 13 points in 12 games for the Sharks and then had 70 points the following season. Injuries slowed him in 2000-01 but he had 46 points in 45 games played. He reamined healthy in his final three seasons, scoring 58 and 61 points and then adding 14 points in 17 playoff games in 2004, his final year in the NHL.

Meanwhile, the Canadiens drafted Marcel Hossa and Kiel McLeod with those two prominent picks. The management team at that time didn't have the self awareness to know they couldn't draft, making trading for draft picks essentially useless.

The Jyrki Lumme Trade

The Montreal Canadiens had plenty of success in the early 1990s and late 1980s but it doesn't mean every move they made was the correct one. They made the Stanley Cup Final in 1989 and won the Stanley Cup in 1993 with a drastically different lineup.

They made a lot of moves in a short time, and while it all worked out in the end, there were a few blunders in the mix as well. One of those was trading away a young, and promising defenseman named Jyrki Lumme.

The Finnish defender was a third round pick of the Canadiens in 1986, shortly after they won a Stanley Cup. He played 54 games with the Canadiens in the 1989-90 season and scored 20 points which is solid production for a young defender just finding their way in the NHL.

Not enough to keep him on the team though. While the Canadiens finished that season well inside a playoff spot, only five teams didn't at the time, they decided to trade away Lumme for a second round pick just ahead of the trade deadline.

Lumme was already an NHL player and only got better. He would go on to become a top pairing defender for the Vancouver Canucks on some great teams and was an ice time leader when they made it to Game 7 of the Stanley Cup Final in 1994.

The Canadiens di win the Stanley Cup in 1993 so this trade didn't derail the franchise, but they could have used a minute munching defender who could put up 40-55 each year.

The Mark Recchi Trade (Not that Recchi trade, the other Recchi trade)

The Montreal Canadiens made a huge blunder when they traded for Mark Recchi. They gave up John LeClair and Eric Desjardins to bring in Recchi and it was a brutal move. Recchi was a good player, a really good scoring winger, but trading him for just LeClair would have been a fair deal.

Adding in a top pairing defenseman like Desjardins just makes the whole deal terrible. Of course, it was not a trade deadline deal though so it doesn't even count in this list.

But the other Mark Recchi trade does. Just four years after paying the Flyers way too much for Recchi, the Canadiens sent him back to Philadelphia, and this time got way too little in return.

Recchi, like Damphousse, seemed to be losing a step offensively but it was only because the team around him was so bad he couldn't produce points all by himself. He had 47 points in 61 games in the 1998-99 season and was shipped to the Flyers for Dainius Zubrus and a second round pick.

Recchi would find his offense once again and had 91 points the following season. And then he just kept piling up points. He had 77 in 2000-01, 75 in 2003-04, 68 in 2006-07, 61 in 2008-09 and 14 points in 25 playoff games in 2011 helping the Boston Bruins win the Stanley Cup.

So, a full decade after the Canadiens moved him he was still a 60 point winger and he was still good enough to be a top six forward on a Stanley Cup winner 12 years after the Canadiens gave him up for futures.

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