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Top 15 Worst Trades in Montreal Canadiens History

The Montreal Canadiens, otherwise known as the bleu, blanc, et rouge, are the most storied franchise in National Hockey League history. Their 24 Stanley Cup championships are not only an NHL record, but they are the measuring stick in all of professional sports. Their legions of fans are not only in la belle province, but throughout the world. In their storied history, some of the most famous names in hockey have donned the CH.

From former All-Stars like Saku Koivu, Steve Shutt, Stephane Richer and Denis Savard, to Hall of Famers and legends like Patrick Roy, The Rocket, the Pocket Rocket, Ken Dryden, Guy Lafleur, Chris Chelios, Larry Robinson, Yvan Cournoyer and the late Jean Beliveau, to current Habs like Carey Price, Andrei Markov, P.K .Subban and captain Max Pacioretty, the Montreal Canadiens have a long and impressive history of names who have played for the team.

Teams of this generation simply cannot deliver a murderer's row as their lineup in an era of high salaries and a cap (think, the Habs in the 50s, 60 and 70s). Unsurprisingly, the majority of entries on this list have taken place from 1980 on. The Habs won 22 Stanley Cups in the first 64 years of the franchise, whereas they only have two since 1980 and haven't won one since 1993. Many will point to the selection of Doug Wickenheiser in the 1980 draft as the beginning of the Canadiens' downfall as a perennial Stanley Cup contender. Others will point to the Patrick Roy trade in 1995 as the single most devastating moment in the franchise's history. Needless to say, that one is on this list.

With that said, we here at TheSportster give you the 15 worst trades in Habs history.

18 Mike Cammalleri, Karri Ramo and 5th Rounder for Rene Bourque, Patrick Holland and 2nd Rounder

Kim Klement-USA TODAY Sports / Kim Klement-USA TODAY Sports

This trade was a perfect example of just how inept, hasty and petty the Habs organization had become. Despite two great years from Mike Cammalleri after signing him, including a 13-goal playoff performance in 2010, just days after making comments about how the team had developed a losing mentality, Cammalleri was traded mid-game to the Flames for Rene Bourque.

The package included the Habs also sending Karri Ramo and a fifth rounder while the Flames threw in a 2nd rounder and Patrick Holland. Bourque had a great 2014 playoff with the Habs but was largely inconsistent in Montreal, often a healthy scratch. All Cammalleri has done is continue to score goals.

17 Andrew Cassels for 2nd Round Pick

via the1jasontaylor.wordpress.com

While the Canadiens didn't give up a big star in this trade, they essentially let a perfectly good no.2 center for nothing. After finding himself with limited playing time with the Habs, Andrew Cassels was traded to Hartford prior to the 1991-92 season for a 2nd round pick, which the Habs used to draft Valeri Bure. Cassels would prove to be an effective playmaker for the Whalers, but could have found more success on a deeper team. Losing depth like this is what slowly killed the Habs as the 90s went on.

16 Jykri Lumme for 2nd Round Pick

via nhl.com

The Habs traded their 1986 3rd round pick in Jyrkie Lumme after his first full season with the team for a 1991 2nd round pick which turned out to be Craig Darby. He would go on to spend nine seasons as a Canuck, where he won the Babe Pratt Trophy, - which was awarded to the club's best defenseman - on four occasions. He became a true staple for their power play.

15 Mike Ribeiro for Janne Niinimaa

via photobucket.com / allhabs.net

Mike Ribeiro has always been a gifted offensive talent, with over 730 career points. However he has always been a headcase.

14 Rogie Vachon for Dale Hoganson, Doug Robinson, Denis DeJordy, and Noel Price

via gameusedmasks.com

The former Vezina winner demanded a trade out from Montreal after he lost his starting job to a young Ken Dryden. The man known as "Rogie", would spend seven seasons with the Kings. He would be named an All-Star four times. He would go on to become arguably the best goalie in franchise history. In 1976, Vachon would also be named the starting goalie for Canada in the Canada Cup where he would go on to make the tournament All-Star team.

13 Bobby Smith for Louis Bernard

via hockeyministies.org

12 Mark Recchi for Dainius Zubrus and Two Draft Picks

via rantsports.com

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An eventual three-time Stanley Cup winner and seven-time All-Star was given back to the team the Habs had paid an arm and a leg to pry him from.

The Habs sent Recchi back to Philly just a few years after acquiring him and ended up with Zubrus. While he became the first Lithuanian player to play 1,000 NHL games, his production with the Habs, along with his over-all career fall well short of Recchi's. In 139 games over three seasons with Montreal, the speedy center had 74 points. Reechi on the other hand, had over 200 in a Habs jersey. While some might look at Reechi's longevity as the reason why he surpassed the younger player, Zubrus who is currently a San Jose Shark, has played one less season than Reechi (22 to 21). The two draft picks turned out to be Matt Carkner and Scott Selig, who never amounted to anything in Montreal.

10 Ryan McDonaugh, Chris Higgins, Pavel Valentenko and Doug Janik for Scott Gomez, Tom Pyatt and Michael Busto.

via nhlsnipers.com

Higgins for Gomez and Pyatt by itself would make this a bad deal for the Canadiens. The fact that former Habs GM Bob Gainey threw in McDonaugh who would develop into a top-2 Defenseman and the current captain of the Rangers was enough to make this list.

In Gomez, the Habs thought they were getting a top line center that would generate instant offense, especially since he would be re-uniting with former Devils teammate Brian Gionta. Gomez was a complete disaster, never living up to his ludicrous contract.

9 Vincent Damphousse for Three Draft Picks

via the1jasontaylor.wordpress.com

8 Claude Lemieux for Sylvain Turgeon

via thehockeyguys.com

Before Brad Marchand and Sean Avery there was Claude Lemieux.

His 80 post-season goals rank him 9th all-time in NHL history. He also played a huge role in the Devils' 1995 Stanley Cup win and was named the Conn Smythe Trophy winner as the playoff MVP. Lemieux who also won the Cup with the Habs in 1986, would also win two more rings with the Colorado Avalanche in 1996 and again with the Devils in 2000.

7 Rod Langway, Doug Jarvis, Brian Engblom, and Craig Laughlin for Ryan Walter and Rick Green

via capitals.nhl.com

At first glance this looks like a solid trade by both teams. The players that the Habs received in the trade would end up being very effective players, playing key roles for their 1986 Stanley Cup win. Unlike many of the players on this list, both Green and Walter would spend a long time in a Habs' jersey, nearly 10 seasons.

With the said, the Caps got an infinitely better deal. In Langway, the Caps got a player who was immediately named captain, and with his strong two-way play helped transform the team defensively. His solid play with his new team also led to him winning back-to-back Norris trophies as the league's best Defensemen in 1983 and 1984.

In Doug Jarvis, the Caps got a player who was not only an excellent two-way player, but someone who ended up being one of the best defensive forwards in NHL history. While Engblom would only go on to play 79 games for Washington, he was part of an eventual trade that landed Larry Murphy.

6 John LeClair, Eric Desjardins and Gilbert Dionne for Mark Reechi and Martin Hohenberger

via espn.com

In search for more offense former Canadiens GM Serge Savard traded three members of their 1993 Stanley Cup winning team in promising big winger John LeClair, solid underrated two-way defenseman Eric Desjardins and Gilbert Dionne for Mark Reechi. With over 1,500 career points, including 222 for Montreal, there's no question that Reechi did provide the Habs with what they were looking for. It wouldn't last long however, as the forward was traded away after just four seasons.

While Dionne did nothing as a Flyer, Desjardins and LeClair developed into stars. Desjardins' superb play on both ends quickly turned him into the team's best defenseman. For LeClair, all the promise that he showed as a Hab finally came to fruition as a Flyer. He along with Philly captain Eric Lindros and dynamic winger Mikhael Renberg would form the Legion of Doom, the best trio in hockey.

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4 Stephane Richer, Darcy Tucker and David Wilkie for Patrick Poulin, Mike Vukota and Igor Ulanov

via nhl.com

This is one of many moves made by Rejean Houle that blew up in his face. Richer became the youngest player in team history to score both 50 goals in a season, and 100 career goals, but was thought to be done at the age of 34. The Habs traded the popular former All-Star along with Darcy Tucker and defenseman David Wilkie to the Tampa Bay Lightning for Patrick Poulin, Mike Vukota, Igor Ulanov. Giving up Tucker was also a significant loss for the Habs as the fiesty forward would turn into a solid agitator who was able to put the puck in the net.

3 Pierre Turgeon, Rory Fitzpatrick and Craig Conroy for Shayne Corson, Murray Baron and 5th Rounder

via icehockey.wikia.com

The Habs once again tried to dig deep into their past when they re-acquired Shayne Corson in a trade with the St. Louis Blues. Corson spent six seasons as a Hab in the late 80s and early 90s. He had bounced around in the 90s and was traded from St. Louis along with Murray Baron for Canadiens' captain Pierre Turgeon, Craig Conroy and Rory Fitzpatrick. Corson proved to be a shell of his former self. During his four-year second stint with the team, he would only crack the 20 goal mark once.

In Turgeon, St. Louis got a first line center they could pair with Famer Brett Hull. As a Blue, he never recorded less than 65 points, and helped propel his new team into a contender in the extremely tough Western Conference. Craig Conroy became a dependable grinder for the Blues. While Fitzpatrick was a sixth defenseman at best, he was still a decent piece.

2 Chris Chelios and Michael Pomichter for Denis Savard

via the1jasontaylor.wordpress.com / espn.com

In an effort to add more offense and perhaps to correct a mistake the team made in the 1980 draft, along with Chelios off-ice issues, the Habs made one of the worst mistakes in franchise history.

While the author of the Savardian Spin-o-Rama was still able to bring some firepower to the Canadiens line-up, - he scored 28 goals in his first two years with the Habs he was past his prime, and his gaudy offensive stats started to slip. Injuries would also play a role in his demise. Before coming to the Habs he had 42 games over his final two years in Chicago.

1 Patrick Roy and Mike Keane for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko

via sbnation.com

This week marks the 20-year anniversary of the trade that shocked the not only a city, but the hockey world. While some people might rank the Chelios/Savard deal as number 1, because the Habs lost a once in a generation player, I rank this trade as the worst in Canadiens history because it cost them arguably the greatest goaltender ever. Losing the heart and soul of the team, in Patrick Roy because he was left out to dry and embarrassed by then head coach Mario Tremblay, set the club back for over a decade, as they didn't find a replacement until 2005 when they drafted Carey Price.

Montreal's decision to include captain Mike Keane in the trade, added more salt to the wound, as the team would miss his grit, defense, and especially his leadership as the club entered a tailspin.

Keane and Roy's arrival in Colorado couldn't have ended any better as the duo helped the Avalanche win the Stanley Cup in 1996, with Roy putting up an incredible 16-6 record in the playoffs with a 2.10 GAA, and three shutouts. Keane left the Avs as a couple of years later but Roy would continue his dominance. He led Colorado to another championship in 2001, while winning his record third Conn Smythe trophy. Roy would be inducted to the Hall of Fame in 2006.

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Top 15 Worst Trades in Montreal Canadiens History