Montreal Canadiens: Five Worst Trades Since 2000

The Montreal Canadiens, like all teams, have made some great trades that make you wonder what the other team was thinking and have also been guilty of some poor swaps. Take a look at their five worst trades since 2000.

The Montreal Canadiens, like much of the rest of the world, are on pause at the moment. Their season came to a screeching halt after 71 games and we still don’t know when, or if, we will see the 2019-20 version of the Habs again.

The team was not exactly dominating on the ice this season. They were ten points out of the final playoff spot in the Eastern Conference, and a perfect 11 game finish to their season likely would not have been enough to get them into the playoffs.

As we await an announcement of when the NHL calendar will start up again, and what it is going to look like when it does, we have been looking back at some of the best and worst decisions the Habs have made this century. We started by looking at the five best draft picks since the 2000 NHL Draft and the five worst decisions on the draft floor since then.

Yesterday, we took a look at the five best trades the Canadiens have made since the year 2000. There were some great ones for sure, with the Habs stealing Phillip Danault and Alexander Romanov away from the Blackhawks for a couple of aging veterans and selling P.K. Subban and Alex Galchenyuk at precisely the right moment.

So, today we will look at the other side of the coin. While the Habs have pulled off some great trades lately, they have made some questionable decisions as well. Let’s take a look at the five worst trades the Habs have made since 2000.

#4: Mikhail Sergachev traded for Jonathan Drouin

The Habs completely renovated their left defence in the summer of 2017 and pretty much every decision was a wrong one. Trading their top prospect was an odd decision for a team that had just lost in the first round of the playoffs and was losing Andrei Markov to free agency.

They acquired a good player in Drouin, but tried to turn him into a centre, thinking he could fill the role of first line centre that was a need in the city for many years. That didn’t work, and while Drouin remains a valuable player, the Habs are just now possibly putting together a decent group of left defencemen.

Sergachev, meanwhile, it developing into quite a defender for the Tampa Bay Lightning. He has increased his ice time dramatically each year with the Bolts, playing over 20 minutes per game this season. He scored 34 points in 70 games.

Drouin had 15 points in his first 18 games of the season but was injured. He returned but was clearly not himself after being off the ice for months. In a vacuum, trading Sergachev for Drouin is not an awful trade, though it still favours the Lightning. When you consider the Habs biggest need is left defence and they thought Drouin played a different position than he actually does, it makes it a poor deal for the Canadiens.

#3: Mike Ribeiro and a sixth round pick traded for Janne Niinimaa and a fifth round pick

The Canadiens made the playoffs in 2005-06 and did so with pretty decent centre depth. They had a 30 year old Saku Koivu who scored 62 points in 72 games, 25 year old Mike Ribeiro scored 51 points in 79 games after breaking out the previous season with 65 points and they had a 22 year old Tomas Plekanec playing on the third line.

Then, they traded Ribeiro to the Dallas Stars on the eve of the 2006-07 season. The teams also swapped late picks but it was basically Ribeiro for Janne Niinimaa. The Finnish defenceman was really good in 2001-02, but by the time this trade was made, he was a 31 year old coming off a 16 point season.

Niinimaa played 41 games for the Habs that season, and was a healthy scratch on many occasions. Following that season, he would not play in the NHL again, leaving North America to play in Switzerland the following year.

Meanwhile, Ribeiro became an offensive weapon for the next decade in the NHL. While the Habs kept looking for more centre depth, Ribeiro was scoring at a point per game pace elsewhere. The Montreal native would score 407 points in 461 games over the next six seasons in Dallas.

He scored 49 points in 48 games in one season with the Washington Capitals as their second line centre. Ribeiro then signed a big contract with the Arizona Coyotes, but was bought out after scoring 47 points in 80 games. That same season, the Habs went to the Eastern Conference final with David Desharnais leading the way in scoring among centres with 52 points.

That was a big step back for Ribeiro, yet even during his worst offensive season he was scoring as much as the Habs best scoring centre. By all accounts, Ribeiro wasn’t the best guy in the world. However, if you decide a good hockey player isn’t worth keeping around, maybe hold out until you get a better offer than an over-the-hill defenceman.

#2: Jaroslav Spacek traded for Tomas Kaberle

The Canadiens 2011-12 season got off to an uneven start. After 29 games, they were sitting with 29 points based on their 11-11-7 record. They began the season with just one win in their first eight games, so scratching and clawing their way back to a record that gave them .500 points percentage was a bit of a relief.

Still, the Canadiens general manager Pierre Gauthier wanted to make some changes to the roster. They were waiting anxiously for Andrei Markov to return to the lineup but a series of setbacks forced him to stay on the injured list throughout the first few months of the season. Another veteran left defender, Jaroslav Spacek wasn’t playing terrific hockey either, scoring just three assists in 12 games by early December.

So, Gauthier decided to trade Spacek, who was in the last year of his contract that paid him $3.8 million, for Tomas Kaberle who was in the first year of his contract that paid him $4.25 million per year. Kaberle had won the Stanley Cup the year before as a third pairing defenceman with the Boston Bruins.

After signing his three-year contract with the Hurricanes, their general manager Jim Rutherford was vocal about his regret and displeasure with Kaberle who had nine assists in 29 games. The Canadiens needed a power play quarterback with Markov injured and thought Kaberle could fill the role.

Also, Gauthier had to know his job was in jeopardy with the vitriol directed his way after the team’s slow start to the season. Kaberle scored 22 points in 43 games with the Habs that season, which isn’t bad production from a defenceman, but not even Jake Gardiner would be jealous of Kaberle’s defensive game.

The Czech Republic native played just ten games the following year, but was mostly asked to stay on the sidelines to avoid injuries. This way, the Habs were able to buy out his contract without any hiccups.

#1: Ryan McDonagh, Chris Higgins, Pavel Valentenko and Doug Janik traded for Scott Gomez, Tom Pyatt and Mike Busto

The Canadiens had a disappointing season during their centennial campaign in 2008-09. Due to this performance, they pretty much decided to get rid of as many players as they possibly could. Saku Koivu, Alex Kovalev, Alex Tanguay, Mike Komisarek, Robert Lang and Mathieu Schneider all left the team as free agents.

That wasn’t enough evidently. The team needed to get rid of a few more players via trade. SO, on the eve of free agent frenzy 2009, the Canadiens traded Chris Higgins, Doug Janik and prospects Ryan McDonagh and Pavel Valentenko to the New York Rangers for Scott Gomez, Tom Pyatt and Mike Busto.

Janik, Valentenko and Busto would not play much more at the NHL level after the deal, so it was essentially Gomez and Pyatt to Montreal for Higgins and McDonagh. It could have been nobody for Scott Gomez and the deal would still be a huge win for the New York Rangers.

Gomez had signed an incredible seven year contract with the Rangers in 2007 worth $51.5 million for an annual cap hit just north of $7.35 million. The salary cap at the time of the trade to Montreal was only $56.8 million. That means Gomez was taking up about 13% of the Habs total cap space when he arrived.

You would think a team trading their top prospect for someone making such a substantial income would be acquiring a terrific player. Gomez was coming off a season with the Rangers where he scored 16 goals and 58 points. I mean, that’s not bad production, but not nearly enough for one of the highest paid players in the league at the time.

Gomez basically matched that production in his first season with the Habs. He scored just 12 goals and had 59 points in 78 games. His second season in Montreal was a colossal disaster as he scored seven goals and 38 points in 80 games, though he was consistently playing top six minutes and top power play. He had 11 points in 38 games the following year, capping off an embarrassing stretch where he went more than a calendar year without scoring a goal.

When the Habs returned from the lockout that wiped out half the 2012-13 season, teams knew they were going to be allowed to use two compliance buyouts at the end of the year. With it being so obvious that Gomez would be bought out, new general manager Marc Bergevin didn’t invite Gomez to training camp, asking him instead to stay home and avoid injury so he could be bought out.

The league stepped in and changed the rule so Gomez could immediately be bought out of his awful contract. Meanwhile, Higgins had some productive years as a third line winger for the Vancouver Canucks who were one of the best teams in hockey at the time.

Just to make the terrible trade even worse, McDonagh turned into a top pairing defender who some Norris Trophy votes in six different seasons in his career. He is just 30 years old now and is still a great defenceman for the Tampa Bay Lightning.