Montreal Canadiens: The 13 Worst Trades in Team History

Scott WeldonCorrespondent IFebruary 26, 2011

Montreal Canadiens: The 13 Worst Trades in Team History

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    Bruce Bennett/Getty Images

    Trade deadline day sometimes brings about a trade that puts a team on the path for a Stanley Cup victory. If your team's general manager makes the right deal he can even start them on the road to dynasty. Unfortunately for every Butch Goring ready to lead his Islanders on a four cup winning streak there are a dozen Alexei Zhitniks ready to help sink his Atlanta Thrashers and lead them back out into the wilderness.

    The Montreal Canadiens have been lucky enough in their history to be lead by some of the greatest general managers in hockey history. From 1940 until 1978 Tommy Gordon, Frank J. Selke and Sam Pollock took the team from one dynasty era to the next seldom missing a beat or making a bad trade.     

    There have been plenty of bad trades through Canadiens' history and this power point is my attempt to rank the 13 worst. You can be pretty sure the GM's listed above will be involved in very few of them. 

    Trades are tough enough without the added pressure of time ticking down to deadline day. Desperate teams often make terrible decisions as the pressure mounts. A bad trade can cripple an organization for years, especially in today's  hard-cap league.  

    This is a cautionary look at those bad trades and what they can do to your organization if you're not careful. 

    The title for each slide will just be the primary player involved in each particular deal. My thanks to  for the dates of all the trades and all the principles involved.    

Almost Made It

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    PITTSBURGH - APRIL 17: John LeClair #10of the Pittsburgh Penguins looks on during the game against the New York Islanders on April 17, 2006 at the Mellon Arena in Pittsburgh, Pennsylvania. (Photo by Bruce Bennett/Getty Images)
    Bruce Bennett/Getty Images

    This is a nod to some of the deals Hab GM's have made over the years that didn't quite make my list. 

    In 1963 all-time great GM Frank J Selke moved all-time great Jacques Plante G to the New York Rangers for Gump Worsley G. While the moving of Plante was similar to the trading of great team icons Howie Morenz and Patrick Roy the truth is that Worsley, when he was finally healthy, put up some Plante-like numbers in Montreal and Plante with the Rangers put up some Worsley-like numbers in New York. The Rangers continued to lose and the Canadiens continued to win like no deal had occurred.

    Frank Selke also traded Hal Laycoe D for Ross Lowe D in 1951. Lowe barely lasted the year while Laycoe became a defensive fixture with the Bruins.

    Half way through 1995 GM Serge Savard traded Stanley Cup hero John Leclair RW, Gilbert Dionne LW, and Eric Desjardins D to the Philadelphia Flyers for Mark Recchi RW and Martin Hohenberger LW. Recchi was great in Montreal but Leclair and Desjardins became pillars on those great Lindros lead Flyer teams that those Canadien teams of the time couldn't compete with. John Leclair was featured on the Legion of Doom line and scored 50 goals three times. The Canadiens haven't had a fifty goal scorer themselves since Stephane Richer in 1989-90.  

    Sam Pollock in 1972 traded Glenn "Chico" Resch G and others to the Islanders for their second round pick Glenn Goldup RW and cash. Yes, sometimes even the master made mistakes.

    Serge Savard was GM in 1983 when he traded away Irving Grundman's first overall pick Doug Wickenheiser RW, playmaker Greg Paslawski C and Gilbert Delorme D to the St Louis Blues for Perry Turnbull LW. Turnbull was a power forward who lasted forty games in Montreal while Doug and Greg played key roles in St Louis.

    Okay now here come the twelve worst trades. 

13. Scott Gomez C : June 30, 2009

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    CALGARY, AB - FEBRUARY 20:  Scott Gomez #11 of the Montreal Canadiens skates against the Calgary Flames during the 2011 NHL Heritage Classic Game at McMahon Stadium on February 20, 2011 in Calgary, Alberta, Canada. The Flames defeated the Canadiens 4-0.
    Andre Ringuette/Getty Images

    Glen Sather, the general manager of the New York Rangers, managed to dump what was considered at the time the most untradeable contract in the NHL. Not only did he dump five years at $7,357,000 a year off his cap onto the Habs' cap he also picked up rental Chris Higgins, defenseman Ryan McDonagh, habs fifth round pick russian defensemen Pavel Valentenko and the rights to Doug Janik.

    He gave up Gomez, a competent playmaking center, Tom Pyatt a fast young checker and Mike Busto who was just that and now plays hockey in Italy.   

    The Canadiens won the trade talent wise. Gomez has provided offense identical to what he managed in his last season in New York. His play in the playoffs was better than that. Tom Pyatt has become an everyday player for Montreal, a fast checking forward.

    McDonagh was the Canadiens first round pick in 2007 (12th overall). The young defense prospect is getting a chance in New York but he certainly has yet to contribute as much as Gomez or even Pyatt.

    Unfortunately, Scott Gomez is making too much money for the offense he provides. His salary is a constant hindrance to any attempts by the team to improve. As a second line center making three to four million a year, Scott Gomez is not a bad player in Montreal. A seven million dollar player with a miserable shot and diminishing skill in the face-off circle is a crippling drag to an organization in a salary cap world.  

12. Mike Ribeiro C : Sept 30, 2006

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    PHILADELPHIA, PA - FEBRUARY 05:  Mike Ribeiro #63 of the Dallas Stars skates against the Philadelphia Flyers on February 5, 2011 at Wells Fargo Center in Philadelphia, Pennsylvania. The Flyers defeated the Stars 3-1.  (Photo by Jim McIsaac/Getty Images)
    Jim McIsaac/Getty Images

    Young scorer Mike Ribeiro C and a sixth round pick were traded to the Dallas Stars for aging Janne Niinimaa D and a fifth round pick by GM Bob Gainey.

    Ribeiro has since had seasons of 59, 83, 78, 53 and 49 points for the Stars. Niinimaa, 31 years old at the time, played 41 games that year for the Canadiens, getting three points. He then left for Switzerland and now plays in the Swedish Elite League. 

    The deal was all about getting rid of the unpopular Ribeiro and making room for the up and coming Plekanec. Still, the two quality seasons the 26 year old had already in the NHL should have been worth more than Janne Niinimaa. 

11. Stephane Richer LW : January 15, 1998

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    15 Mar 1997:  Rightwinger Stephane Richer of the Montreal Canadiens looks on during a game against the Ottawa Senators at The Forum in Montreal, Quebec.  The game was a tie, 2-2Mandatory Credit: Robert Laberge  /Allsport
    Robert Laberge/Getty Images

    Stephane Richer RW, Darcy Tucker LW and young David Wilkie D were traded by general manager, Rejean Houle, to the Tampa Bay Lightning for Patrick Poulin LW, Mike Vukota RW and Igor Ulanov D. 

    Richer at this point in his career was no longer the offensive force he had been when the Canadiens had traded him away the first time back in 1991 for Kirk Muller. His career never rebounded in Tampa Bay and his best season there was 12 goals and 33 points in 64 games in 1998-99.

    Darcy Tucker, on the other hand, was just beginning to bloom as that irascible checker and scorer he was to become in Toronto a couple years later. For Tampa Bay Tucker managed 21 goals and 43 points in 82 games and played a role beyond his offensive, one as an agitator. 

    David Wilkie's career pretty well ended in Tampa Bay and he never made it as full time NHL defenseman.

    Patrick Poulin had been a first round pick by the Hartford Whalers (ninth overall) back in 1991 who had never panned out. The Montreal Canadiens desperately attempted to make a player out of him for four and a half long years. After watching Poulin play for ten minutes it became painfully apparent that he was just too slow to be an NHL player. He scored 10 goals one year and 25 points another but his presence in the line-up was mostly just a drag on the team. He never equalled his rookie season in 1992-93 with Hartford when he had 20 goals and 51 points.

    Mick Vukota played 22 games with Montreal and never scored a point. He left for the IHL never to return.

    Igor Ulanov only lasted one full season and bits of two others in Montreal. He was a fearsome hitter but his skating was questionable and the hard edge he brought to the game had him injured, a lot.

    The Canadiens gave up players in this deal who were contributing for players from Tampa Bay who couldn't contribute in Montreal. The best man they got in the deal was Ulanov and he was a one trick pony who didn't stick around. The best player Tamp Bay got was Darcy Tucker who managed to play 12 more NHL seasons before he was done.   

10. Gordon "Red" Berenson C : June 13, 1966

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    DENVER - APRIL 09:  Head coach Red Berenson of the Michigan Wolverines directs practice for the 2008 Men's Frozen Four Championship at the Pepsi Center on April 9, 2008 in Denver, Colorado.  (Photo by Doug Pensinger/Getty Images)
    Doug Pensinger/Getty Images

    Gord "Red Baron" Berenson C had a three year tryout in Montreal before GM Sam Pollock traded him to the New York Rangers for Ted Taylor LW and Garry Peters C.

    Peters banged around the NHL and never scored more than eight goals in a season. Ted Taylor scored 11 as a Canuck before finding his niche in the WHA.

    Red Berenson played an uneventful year in New York and then joined the St Louis Blues and became their number one center. He was a point a game player with the Blues with seasons of 35 and 33 goals scored. He played 17 seasons in the NHL and scored a total of 261 goals and 648 points in 987 games.    

9. Jyrki Lumme D : March 6, 1990

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    Mike Powell/Getty Images

    Jyrki Lumme D played a year and a half in Montreal before GM Serge Savard decided to deal him for the Vancouver Canucks second round pick. That pick wound up being Craig Darby C, a 6'1" 200lb kid from New York. Darby lasted a couple of seasons in Montreal before being demoted to the AHL where he spent the bulk of his career.

    Lumme on the other hand was a quality offensive defenseman for the Vancouver Canucks for nine years. Lumme had a career best 55 points in 1993-94 and another 13 in 24 playoff games as he helped the Canucks to the Stanley Cup finals where they finally lost to the New York Rangers.

    Lumme was a consistent half point a game defenseman for his whole career and better than that in Vancouver. He played another six years in the NHL after leaving Vancouver. 

8. Vincent Damphousse C : March 23, 1999

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    CALGARY, ALBERTA, CANADA - MAY 13:  Vincent Damphousse #25 of the San Jose Sharks scores a goal on a backhand shot against the Calgary Flames during Game three of the 2004 NHL Western Conference Finals on May 13, 2004 at the Pengrowth Saddledome in Calgar
    Elsa/Getty Images

    Late in the 1998-99 season Montreal Canadien team leader Vincent Damphousse C was traded by then GM Rejean Houle to the San Jose Sharks for picks. The trading of a veteran for draft picks is often considered the bright move to make for a team in decline. The  Canadiens were in decline, six years from their last Stanley Cup win they were destined to finish dead last in the Northeast division, out of the playoffs.

    Houle traded Damphousse for a fifth round pick in 1999, a conditional pick that became a first round pick in 2000, and a second round pick in 2001. Any GM could be proud of that deal. Unfortunately for Les Habitants, at age 31 Vinnie was not ready to retire. He played another five plus seasons for the Sharks getting in 385 games and scoring 92 goals and 289 points. He had three 20 goal or more regular seasons in San Jose and helped them in three deep playoff runs. The best of those was his last year in San Jose when he had 14 points in 17 games as the Sharks made it to the Western Conference finals for the first time in their history, only to lose to the Calgary Flames in six games.

    The Canadiens' draft picks on the other hand didn't fare as well. The second round pick was traded to Columbus. They chose Kiel McLeod (53rd overall, 2001). McLeod never made the NHL, played in Europe and currently plays for the Victoria Salmon Kings of the East Coast Hockey League.

    The fifth round pick (145th overall, 1999) became Marc-Andre Thinel who never made the NHL. He has spent the last five years tearing up a league in France for Rouen.

    The first round pick (16th overall, 2000) was Marion Hossa's little brother Marcel. A talented skater, he got into 59 games as a Montreal Canadien but never scored more than six goals in a season for them. The Rangers and Coyotes tried him out but Marcel has ended up in the KHL playing for Kazan Ak-bars.        

7. Danny Grant RW: June 10, 1968

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    Montreal Canadiens' former GM Sam Pollock is rightfully known as one of the best general managers in the history of the franchise and the NHL itself. His biggest claim to fame was his manipulation of the six new franchises that joined the NHL in 1967-68.

    He was renowned for trading surplus veterans to the talent needy teams for their first and second round draft picks. Those deals lead to him acquiring the cornerstones of the 1970's and 80's dynasty hab teams like Guy Lafleur, Steve Shutt, Chuck Lefley and Michel "Bunny" Larocque.  

    It's important for the record to show that those deals didn't always work out.

    In 1968 Pollock traded Canadiens' prospect Danny Grant RW, Claude Larose LW, and future considerations which turned out to be Marshall Johnson RW to the Minnesota North Stars for cash, their first round pick in 1972 (Dave Gardner C) and future considerations (Bob Murdoch D).  

    Johnson played bits of five seasons with the North Stars contributing little.

    Larose was a talented checker who also could score you 20 goals a season. He had two 20+ goal seasons for Minnesota before Sam Pollock felt compelled to trade young talented Bobby Rousseau to Minnesota to get him back.

    The best player in the deal turned out to be the untried prospect from Fredricton, New Brunswick, Danny Grant. Danny was the league rookie of the year his first season in Minnesota.

    Danny played six years in Minnesota and was one of their best players that entire time. He had three plus 30 goal seasons and two where he scored 29 with the North Stars. Traded to the Red Wings as a 29 year old he had his best NHL season ever with 50 goals and 86 points in 80 games.

    Bob Murdoch was a competent offensive defensemen in Montreal but only played 81 games before being traded to Los Angeles.

    Dave Gardner proved to be one of the worst first round draft picks in Montreal history. The center was taken eighth overall in 1972. He played two years and 36 games in Montreal amassing two goals and 11 assists. He banged around the league playing for the California Golden Seals and Cleveland Barons among others.     

6. Chris Chelios D : June 29, 1990

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    17 Jan 1998:  Chris Chelios of the Chicago Blackhawks in action during the skills competition during NHL All-Star Weekend at General Motors Palace in Vancouver, Canada. Mandatory Credit: Robert Laberge  /Allsport
    Robert Laberge/Getty Images

    Chris Chelios D and a second round draft pick in 1991 (Mike Pomichter C) were traded by Serge Savard of the Montreal Canadiens to the Chicago Blackhawks for Denis Savard C. The deal at the time smelled of an attempt to right the wrong that had been perpetrated when then-GM Irving Grundman had drafted checker Doug Wickenheiser rather than the talented frenchman Savard back in 1980.

    Unfortunately for Montreal, by the time they got Savard, despite the fact he was only 29, he was in decline. Still a very talented player he never approached the career best 131 points he had in Chicago three years earlier. He lasted three seasons in Montreal and never had more than a point a game in a season. He was in the league for another five years after that finishing his career as he started it, in Chicago.

    Chelios on the other hand proved to be perhaps the most durable defenseman in the history of the NHL. He played nine more seasons in Chicago twice scoring more than 70 points in a season. In fact his 72 and 73 points in 92-93 and 95-96 were both higher totals than anything the center Savard managed in his time in Montreal. He was a critical member of the Blackhawks for almost a decade and a key part of two deep Chicago playoff runs.

    As his offensive skills waned he was traded to the Detroit Red Wings  where he played in another 10 NHL seasons. When Chris Chelios finally hung up his skates last year, Denis Savard had been out of hockey for a dozen years.   

5. Rod Langway D : September 9, 1982

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    TORONTO - NOVEMBER 12:  Rod Langway #25 of Team World and Steve Shutt #22 of Team Canada battle in front of the net during the Hockey Hall of Fame Legends Classic game at the Air Canada Centre November 12, 2006 in Toronto, Ontario.  (Photo by Bruce Bennet
    Bruce Bennett/Getty Images

    Irving Grundman was known for a variety of stupid personnel moves he made in his short tenure as ownership's choice to replace one of the most successful GM's in Montreal Canadiens' history, Sam Pollock. He didn't make a lot of trades of significance while at the helm in Montreal.

    The biggest trade he made was the worst. He sent Rod Langway D, Brian Engblom D, Craig Laughlin RW and checker and face-off artist Doug Jarvis C to Washington for a couple of highly regarded players Ryan Walter C and Rick Green D.

    Ryan Walter had been chosen second overall by the Capitals in the 1978 NHL entry draft. He was coming off what turned out to be the best season of his career (1981-82) where he had 38 goals and 87 points. Walter played in Montreal and contributed for the next nine years, but he never managed to produce more than 50 points in a season. He scored 20 goals or more twice as a Canadien. The hard-nosed Walter proved to be a painfully slow skater who didn't fit into the Montreal Canadien identity. His style of play usually had him missing around 10 games a season. He was a big contributor during the Canadiens' Stanley Cup winning run in 1987. He had seven goals and nineteen points on the way to the cup.

    Rick Green was a huge defenseman who had been the Capitals first round pick (No. 1 overall) in 1976. He was expected to be a great offensive defenseman in the NHL. Like Walter, however, he was an incredibly slow skater. He was a talented player and managed 41 points one year in Washington but was never really a good enough skater to be a quality NHL offensive defenseman.

    Green played seven years in Montreal and was a huge contributor. He found his niche as a big defensive defenseman who kept the front of his net clear. Green spent a lot of time injured as well.

    Washington, on the other hand, picked up Craig Laughlin who basically seemed like a throw-in in this deal. Laughlin played six seasons in Washington. He had 30 goals and 75 points in 1985-86. He had twenty goals or more three times and more than 50 points four times.

    The linch-pin of the deal was Rod Langway. Much more mobile than Green he became their chief shut-down defenseman for his 11 seasons in Washington. He won two back to back James Norris trophies as the best defenseman in the league in the early eighties for the Capitals. Langway is one of the only strictly defensive defensemen ever to win the honour. He won the trophies while scoring 33 and 32 points. The last time that happened was 1967-68 when Bobby Orr won his first James Norris trophy after scoring 31 points in 46 games.

    Brian Engblom was another good defensive defenseman but he only played a year and a half in Washington.

    The last bit of the puzzle that Grundman traded away was checking center Doug Jarvis. Jarvis played three and a half years in Washington never missing a game and won the Frank J. Selke trophy as the best defensive forward in the game in 1983-84.                         

4. Pierre Turgeon C : October 29, 1996

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    iMONTREAL- DECEMBER 4:  Former Montreal Canadien Pierre Turgeon skates during the Centennial Celebration ceremonies prior to the NHL game between the Montreal Canadiens and Boston Bruins on December 4, 2009 at the Bell Centre in Montreal, Quebec, Canada.
    Richard Wolowicz/Getty Images

    GM Rejean Houle put the last nail in the Habs' coffin with this, his follow up to the Patrick Roy trade from the year before. This time he traded Pierre Turgeon C, career minor leaguer Cory Fitzpatrick and Craig Conroy C to the St Louis Blues for winger and former Hab Shayne Corson LW, semi-goon Murray Baron D and a fifth round pick (Gennady Razin).

    The previous year had seen the departure of the aforementioned Roy. The Canadiens lost in the first round of the playoffs in six games to the New York Rangers. Pierre Turgeon, despite being Montreal's best player in that series and having 38 goals and 96 points in the regular season, was blamed for that loss.

    Nine games into the next season he was moved with the others. He played five seasons in St.Louis, his best being his last where he had 30 goals and 82 points in 79 games. He followed that up with 15 points in fifteen playoff games for the Blues.

    Craig Conroy played five years as a fast skating offense capable checking forward.

    The Habs, on the other hand, enjoyed 60 games of Murray Baron—one of the dirtiest, worst skating defensemen of all time.

    Shayne Corson was traded for to add the grit that Turgeon didn't have. Unfortunately, the gritty Corson had ground down since his first time in Montreal. He played four years in Montreal with his best season being the 21 goals and 55 points he managed in 1997-98. By the end he was barely a third of a point a game player in Montreal.

    The Montreal offense spent years trying to recover from the loss of Turgeon. It also marked a point in Habs' history where they seemed insistent on trading their team captain, every year if possible.  

3. Ted "Teeder" Kennedy C: February 1943

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    Ted "Teeder" Kennedy started in hockey as a Montreal Canadiens prospect. He left their training camp as a homesick 16 year old. He finished the year playing with his home town Senior team for former NHLer Nels " Old Posion" Stewart.

    Nels it was said told the young Kennedy that Leafs coach Hap Day was an expert at developing young players. When then Toronto Maple Leaf general manager Frank J. Selke orchestrated a deal for the young prospect Ted was thrilled to come to Toronto.

    Selke had been left in charge of operations of the Toronto Maple Leafs while the managing director, the legendary Conn Smythe, was serving overseas in World War II. Selke traded defensive prospect Frank Eddols to the Canadiens for Ted Kennedy.

    Frank Eddols went on to play for the Canadiens. He had a NHL career that lasted 317 games spread over eight seasons with Montreal and the Rangers. 

    Ted "Teeder" Kennedy went on to become one of the, and perhaps "the" greatest Toronto Maple Leaf player of all time.

    Kennedy played 14 seasons for the Leafs. He won five Stanley Cups in Toronto. Kennedy was the last Leaf to win the NHL's Hart memorial trophy as the league's most valuable player in 1955.

    Kennedy was voted into the NHL Hall of Fame in 1966.

    Selke participated in the trade that was probably the best in Leaf's history and one of the worst in Montreal Canadien's history. For his trouble in getting one of the all-time Leafs into the fold Selke was blamed by as disgruntled Conn Smythe for not winning the Stanley Cup for the 1945-46 season. It was said Smythe never forgave long time assistant Selke for making the trade without consulting him,

    Selke subsequently resigned and was snapped up by the all too recently fleeced Canadiens.Selke was the Canadien GM for the next 18 years. He took a financially struggling organization and built into one of the great dynasties in sports. Selke then left an able replacement in the legendary Sam Pollock. Ironically one of the worst trades in Montreal Canadiens history lead to the acquisition of one of the greatest general managers in team history.

    Thanks to poster "Big Bubba" who picked up on the Ted Kennedy trade as one of the worst Montreal Canadiens trades of all time. I completely missed that one. It took me a while but I finally added it.                 

2. Howie Morenz C : Oct 3, 1934

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    Howie Morenz C, Lorne Chabot G and Marty Burke D were traded by GM Leo Dandurand to the Chicago Blackhawks for Lionel Conacher C, Leroy Goldsworthy RW and Roger Jenkins D in what was a salary dump for the financially struggling Canadiens.

    Conacher, the best player with the biggest salary coming the other way in the deal, was immediately moved to the Montreal Maroons for Nels Crutchfield C. Leroy Goldsworthy was given back to Chicago for cash two weeks later.  

    Roger Jenkins played a season of defense in Montreal. Crutchfield played a season at center managing five goals and ten points in 41 games.

    Chabot played a full season with Chicago winning the Vezina trophy with a 1.80 GAA.

    Marty Burke played five years in Chicago as a competent defensive defenseman and finally finished his career in Montreal.

    Morenz was the best player of his era. He was selected the best NHL player of the first half of the twentieth century. Dubbed "The Mitchell Meteor" and "The Stratford Streak," he was credited as the most exciting player of his time.

    It's said after watching Morenz play in 1924-25, promoter Tex Rickard installed an ice plant in the new Madison Square Gardens, then still being constructed. He sought out an owner and bootlegger Bill Dwyer bought the Hamilton Tigers for $75,000 (ten times what the current owners had paid for the franchise) and moved it to New York to become the New York Americans and join Boston as an American team in the NHL. He negotiated to get Morenz and Montreal into the gardens to be the Americans' first opponents.

    Howie Morenz is often credited with being one of the drivers of the first big expansion by the NHL into the United States. By 1926-27 the NHL was a ten team league with six US franchises: Boston Bruins, Pittsburgh Pirates, New York Americans, New York Rangers, Chicago Blackhawks and Detroit Cougars.

    The Canadiens won their last cup with Morenz in 1931. The great depression and Howie's diminishing skills lead to the trade.  They didn't win again until Rocket Richard came along in 1943-44 to fill the void left by the departure of Howie Morenz.    

1. Patrick Roy G : December 6, 1995

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    MONTREAL- DECEMBER 4:  Former Montreal Canadiens Serge Savard hands a puck to Patrick Roy during the Centennial Celebration ceremonies prior to the NHL game between the Montreal Canadiens and Boston Bruins on December 4, 2009 at the Bell Centre in Montrea
    Richard Wolowicz/Getty Images

    Rejean Houle as general manager had this trade thrust upon him by a petulant Patrick Roy who was dealing poorly playing for a bad Montreal team.

    He dealt worse with being left in a game where he was being pasted 9-1 on the way to an eventual 11-1 Montreal loss to Detroit. When he was finally pulled, Roy stormed behind the bench and then back to where team president Ronald Corey sat to give him a piece of his mind.

    The trade happened four days later. Patrick Roy G with two Stanley Cups and two Conn Smythe trophies under his belt and team captain Mike Keane RW were traded to the Colorado Avalanche for journeyman Jocelyn Thibault G and offensive forwards Martin Rucinsky LW and Andrei Kovalenko RW.

    This is easily the worst trade in Montreal Canadiens' history— it often makes the list for worst NHL trade of all-time and sometimes can be seen among the worst sports trades of all-time. Like the Morenz deal this trade left Montreal a shattered team that has since experienced some of the worst moments in the franchise's long history.

    Since "Le Trade" the Canadiens have missed the playoffs five times and gone 6-9 in playoff series. Last season was the first time since Roy left that Montreal has won two playoff series in one year. They have not won a Stanley Cup or even played for one since 1993 when Patrick lead them there. This is the longest drought between cup wins in franchise history.

    Patrick joined the former Nordiques just in time to be the key element in their first Stanley Cup win as the Colorado Avalanche. He won a second cup and his third Conn Smythe trophy with Colorado in 2001.

    Patrick spent seven and a half years in Colorado as one of the best goalies in hockey.

    Mike Keane played two years in Colorado as a quality checking forward. He was also obviously a member of the first Stanley Cup winning team and was back when they won the cup again.

    Jocelyn Thibault was given the impossible task of replacing St Patrick in Montreal. He had some good years and lasted for the better part of four seasons before being moved.

    Andrei Kovalenko had 17 goals and 34 points in 51 games for Montreal and then was traded to the Edmonton Oilers.

    Martin Rucinsky was the best player to join Montreal in the deal and he lasted for six years. During his first year he was more than a point a game player. He was always a quality offensive force in Montreal.   

Worst Trading GM in Montreal History

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    MONTREAL - JANUARY 24:  Rejean Houle arrives for the Honda NHL Superskills competition as part of the 2009 NHL All-Star weekend on January 24, 2009 at the Bell Centre in Montreal, Canada.  (Photo by Nick Laham/Getty Images)
    Nick Laham/Getty Images

    Rejean Houle heads the list with the most bad trades on his resume. He has four of the ten worst trades in Canadien's history with his name attached to them including the Patrick Roy deal, the Pierre Turgeon trade, the Damphousse dumping and the second Stephane Richer deal. There isn't much in the way of positive trades to his credit to balance the record either. Most of Houle's deals were reactionary. Even when he got proactive and tried to trade Damphousse before he was too old he blew and manged to get rid of him about four years too early.

    Some other great or near great Montreal GM's also grade out high on this list. Sam Pollock also has three of the bad trades I've mentioned in this slide-show on his record. Mostly that's a function of the shear quantity of deals he did. The majority of those deals were good ones and the quality of the teams he put together speaks for themselves.

    Serge Savard ends up with four of the top 17 bad deals I end up mentioning. He doesn't have the success Pollock had to excuse himself with though he did make many more good trades than Houle ever contemplated.  

    I'm convinced if Irving Grundman had lasted longer and just made more trades he would have been the worst trader in Canadien history by far. He might have been a whiz at putting together a contract or counting gate receipts but he showed himself to be just about the worst talent evaluator in 100 years plus of Montreal Canadien's general managers.       

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