Top 15 Moves the Montreal Canadiens Completely Regret

The Montreal Canadiens are not just one of most historic hockey teams of all-time, they are one most historic teams in the history of sports. They were founded all the way back in 1909 and they have b

The Montreal Canadiens are not just one of most historic hockey teams of all-time, they are one most historic teams in the history of sports. They were founded all the way back in 1909 and they have been a part of the National Hockey League since 1917. Throughout the years, they have won over twenty Division championships. The most important feat, is the fact they have won a record twenty-four Stanley Cup Championships. The next closest team in Stanley Cup wins is the Toronto Maple Leafs with thirteen. Montreal was still able to be a dominate team post the 1967 NHL Expansion. From 1967 to 1993. they were still able to capture ten Stanley Cup's. This including a run of four straight consecutive Stanley Cup wins from 1976-79.

However, with as long of a history as the Montreal Canadiens have, there has certainly been some bumps on the road. There has been some bad free agent signings in which players were just not the right fit, or were being overpaid. There were some terrible trades in which they traded future Hall of Fame players and got little in return. There has also been some bad draft choices, selecting players who turn out to be busts, while passing on future NHL superstars. Finally there has been some awful head coach and general manager hirings, that took years for the team to recover from. It's very possible that the Canadiens could have won more than twenty-four Stanley Cups, had they in hindsight not made some of these poor decisions. Some of these choices only had a short term effect, but some these decisions were so horrible that the franchise has never recovered.

Here are the top 15 moves the Montreal Canadiens completely regret.

15 Signing Sergei Samsonov


Montreal signed Sergei Samsonov on July 12th, 2006 to a two year contract worth $7.05 million. It's hard to blame the Canadiens for taking a chance on Samsonov, as he was coming off an impressive playoff performance with the Edmonton Oilers. In 24 playoff games with the Oilers, he recorded 15 points, helping the huge underdog team make it all the way to the Stanley Cup Finals. Before his stint with Montreal, Samsonov averaged .73 points per game, with the Canadiens he averaged just .41 points per game. He was clearly not a fit with the Canadiens. His stay in Montreal only lasted a total of 63 games. The signing of Sergei Samsonov will go down as one of the worst free agents signings in Montreal Canadiens history.

14 Hiring Irving Grundman as GM


Irving Grundman spent five seasons as the General Manager of the Canadiens from 1978 to 1983. The team only had one Cup win under Grundman, but had great regular season success. They posted at least 100 points in four out of five seasons.

Grundman drafted some great future Canadiens players like Guy Carbonneau, Chris Chelios, and Claude Lemieux, but it was who he didn't draft that would define his legacy. The Canadiens had the first overall pick in the 1980 NHL Entry Draft and the fans were sure that Montreal would select Quebec native Denis Savard. However, Grundman went against what the fans wanted and selected Doug Wickenheiser. Savard went on to become a star in Chicago and scored over 1,000 points (partially with the Canadiens at a point), while Wickenheiser only played parts of four mediocre seasons for the Habs. It sucks for one move to tarnish someone's legacy, but that's exactly what happened to Irving Grundman.

13 Trading Guy Carbonneau for Jim Montgomery


On August 14th, 1994, the Canadiens traded Guy Carbonneau to the St. Louis Blues for Jim Montgomery. Carbonneau played on Montreal for thirteen years and in that time he was one of the league's best two-way forwards. He won two Stanley Cups with Montreal, one in 1986 and the other in 1993.

Jim Montgomery had a fantastic college career at the University of Maine. In 170 games with the University of Maine, he recorded an impressive 301 points. His rookie season with the Blues wasn't overly impressive, recording 20 points in 67 games. At the time of the trade, Guy Carbonneau's play was surely on the decline. The one thing Carbonneau still had though, was excellent leadership skills, something you couldn't easily find.

Montogomery would never find any success in the NHL, he ended only playing five games for the Canadiens. The Habs basically gave up their former captain Guy Carbonneau for nothing.

12 Signing Mike Cammalleri


On July 1st, 2009, the Montreal Canadiens signed Mike Cammalleri to a five year contract worth $30 million. Cammalleri was coming off a career season with the Calgary Flames where he scored 82 points, which included 39 goals. He was 27 at the time of the signing and was entering the prime of his career. His run in Montreal would last just two and a half seasons. Cammalleri put up respectable numbers, but he had trouble staying healthy, missing 32 games during his two full seasons with the Canadiens.

During the 2011-12 season, Cammalleri was very vocal about the team having a loser mentality. He also was not happy about the playing time he was getting under their new interim head coach Randy Cunneyworth. It was only days later that the Canadiens would pull Cammalleri out of a game against Boston, notifying him that he had been traded to the Calgary Flames.

11 Trading Claude Lemieux for Sylvain Turgeon


On October 9th, 1989, Montreal traded Claude Lemieux to New Jersey for Sylvain Turgeon. Lemieux was just 24-years-old at the time of the trade, but already played parts of six seasons with the Canadiens. The offense first Turgeon spent the first six seasons of his career with the Hartford Whalers, where he had the most success of his NHL career.

Claude Lemieux would go to play five seasons for the New Jersey Devils, arguably the best years of his career. His biggest accomplishment with the Devils came during the 1994-95 season, when he led New Jersey to the Stanley Cup, winning the Conn Smythe as playoff MVP.  Turgeon would play just two injury plagued seasons with Montreal. In 75 total games with the Canadiens, he recorded just 32 points.

10 Drafting Mark Napier Over Mike Bossy


By all accounts, Mark Napier had a pretty decent NHL career. He played 11 NHL seasons after being  drafted by the Canadiens in the 1977. He spent six seasons with the Canadiens, which turned out to be the best seasons of his career. In his last two seasons with Montreal, he recorded back to back forty goal seasons.

Arguably the best player to come out of the 1977 Draft was Mike Bossy, who went 15th overall to the New York Islanders and who grew up right outside of Montreal in Laval. Bossy absolutely tore it up in the QMJHL, scoring 309 goals in 263 games. Despite those remarkable stats, scouts were saying Bossy was too timid of a player for the NHL. Not only did the Canadiens pass on Bossy, but the Maple Leafs and Rangers twice passed on taking him.

9 Trading Away Rod Langway


On September 9th, 1982, the Canadiens traded Rod Langway, Doug Jarvis, Craig Laughlin and Brian Engblom to the Capitals for Ryan Walter and Rick Green.

Langway spent four seasons with the Montreal Canadiens and was known as an old school type of defenseman, who wasn't afraid to block shots, and always made sure to clear the the crease of opposing players. The Canadiens had wanted to keep Langway, but he wanted to go to an American based team due to the low Canadian dollar, so Montreal's hands were forced to make a trade.

The acquisition of Langway played immediate dividends for the Capitals. He won back to back Norris Trophies in 1982 and 1983, as the leagues best defenseman. Rod Langway may have forced the Montreal Canadiens to make a trade, but that doesn't let them off the hook. For a future Hall of Fame player like Langway, they should have been able to get some more back in return.

8 Drafting Terry Ryan


Terry Ryan had a great combination of skill and grit while in junior hockey. He could scored goals with the best of them, but wasn't afraid to go to the dirty places. The Canadiens used the eighth overall pick in the 1995 NHL Entry Draft on Ryan. That was the highest draft pick Montreal had since they took Petr Svoboda with the fifth overall selection in 1984.

Ryan played his first pro season in 1997-98, spending most of the season with Montreal's farm team in the AHL. He would go on to spend just three seasons with Montreal. While he excelled at the AHL level, he was not able to translate his skills to the NHL. He went scoreless in his eight games with the Canadiens, the only NHL games of his career.

Jarome Iginla went three picks after Ryan, who has scored over 600 goals in his career. The drafting of Terry Ryan is easily one of the worst draft busts in Montreal Canadiens history.

7 Multi-Player Swap with Flyers


On February 9th, 1995, the Montreal Canadiens traded John LeClair, Eric Desjardins, and Gilbert Dionne to the Philadelphia Flyers for Mark Recchi and a third round draft pick.

LeClair would go on to play ten seasons with the Philadelphia Flyers, where he would become one of the top goal scorers in the NHL. He would score fifty-plus goals in three consecutive seasons. Desjardins would have his best offensive years with the Flyers. In 738 games with the Flyers, he recorded 396 points. Recchi would play four seasons with the Canadiens where he would become one of their offensive leaders.

Mark Recchi's run as a Montreal Canadien wasn't considered a complete failure, but both LeClair and Desjardins made way more of an impact with their new team.

6 Trading Away Chris Chelios


On June 29th, 1990, the Canadiens traded Chris Chelios along with a second round draft pick to the Blackhawks for Denis Savard. Chelios had played seven seasons with the Canadiens, helping Montreal capture the Stanley Cup in 1986. He was also not too far removed from winning the James Norris Trophy, as the the leagues best defenseman in 1988-89.

The fans of the Montreal Canadiens had always wanted Denis Savard to be on their team, ever since they passed on him in the 1980 NHL Draft. Savard was an offensive star for Chicago, as in 736 games he amassed 1,013 points. However, at the time of the trade, Savard was injury plagued and was starting to slow down.

Chelios went on to play nine seasons with Chicago, winning another two Norris Trophies, in 1993 and 1996 respectively. Denis Savard would play just three seasons with the Canadiens. Although he would win a Stanley Cup with Montreal in 1993, his numbers were nowhere near to what they were in his prime years with Chicago and he was injured for a portion of that playoff run.

5 Hiring Mario Tremblay as Head Coach


Mario Tremblay spent 12 seasons with the Canadiens as a player and over time he became one of the best defensive forwards in the game. He was also known as one of hardest working players on the team, who wasn't afraid to get in the corners.

The Canadiens fired head coach Jacques Lemaire shortly into the 1995-96 season and named Mario Tremblay the new head coach. Although Temblay had no previous coaching experience, they were hoping that the exceptional work ethic he had during his playing days would rub off on the Montreal players.

During his very first season, Tremblay was involved in an incident that would define his coaching career. Tremblay was always at odds with Canadiens starting goalie Patrick Roy and on December 2nd, 1995 things came to a head. In a game against the Detroit Red Wings, Roy was left in by Tremblay for nine goals and that would be the last game Roy ever played for the Le Bleu-Blanc-Rouge.

4  4. Trading Ryan McDonagh for Scott Gomez


On June 30th, 2009, the Canadiens traded Chris Higgins, Ryan McDonagh, Pavel Valentenko, and the rights to Doug Janik to the Rangers for Scott Gomez, Tom Pyatt and Mike Busto. The two players of relevance in this trade were Scott Gomez and Ryan McDonagh.

Gomez had a decent first season with the Montreal, recording 59 points, plus another 14 points in the playoffs. His second season was an disaster, as he scored a career low 38 points. His third season was even worse, in 38 games he scored a measly eleven points. In January 2013, the Canadiens bought out the rest of Scott Gomez' contract.

Every since his first full season with the New York in 2011-12, McDonagh has been the Rangers best all-around defenseman and is now their captain.

3 Drafting Doug Wickenheiser


Doug Wickenheiser had a rough time in Montreal before his NHL career had even begun. The first overall pick in the 1980 NHL Entry Draft had a fantastic junior career with the Regina Pats, scoring 170 points in his final year. However, that wasn't enough for Canadiens fans, as they were expecting Montreal to select Quebec native Denis Savard with the first pick instead of Wickenheiser. Savard would end up going to Chicago with the third selection in the draft.

Wickenheiser struggled in his rookie season with just 15 points in 41 games. Savard on the other hand, was a rookie sensation, recording 75 points. Wickenheiser would only last two and half seasons with the Canadiens without making any real impact. Savard's number's would only get better in his time with the Blackhawks.

2 Trading Away Patrick Roy


December 2nd, 1995 is a day Montreal Canadiens fans will never forget. The Canadiens were playing the Detroit Red Wings, a game they ended up losing 11-1. Montreal head coach Mario Tremblay left Patrick Roy in net for nine of those. It is safe to say that Roy was not to happy about that. Roy told the team president Ronald Corey that he had played his final game for the franchise. The Canadiens were now forced to trade one of the best goalies in the team's long history. A few days later on December 6th , 1995, they traded Roy to Colorado.

Patrick Roy would go on to have eight stellar seasons with the Colorado Avalanche and won a Stanley Cup in his very first season with the team. He won the last Stanley Cup of his career in 2001 with Colorado, winning the Conn Smythe as playoff MVP in the process.

A goalie is one of the most important positions in the game of hockey. When the Canadiens traded Patrick Roy, they wasted years trying to find a replacement.

1 Hiring Réjean Houle as GM


On October 21st 1995, the Montreal Canadiens hired Réjean Houle as the 13th General Manager in the team's history. He led the team to the playoffs in his first three seasons, but Montreal never got past the second round. The 1998-99 season was his worst when it came to the standings. Montreal finished last in its division for the first time in 59 years. He would last one more season before being fired at the beginning of the 2000-01 season.

Houle's track record when it came to trades was not so great in his five seasons with the Canadiens. In his very first season, he made the most controversial trade in Canadiens history, when he traded star goaltender Patrick Roy to Colorado. He also traded star players like Mark Recchi, Vincent Damphousse, and Pierre Turgeon and got little to nothing in return.

When it came to drafting, he drafted a lot more duds than studs. The six players who he drafted in the first round, went on to only play a combined 264 games with Montreal and only put up 48 points. Réjean Houle is the worst General Manager in the history of the Montreal Canadiens.

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Top 15 Moves the Montreal Canadiens Completely Regret