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Bob Gainey is definitely one of the most memorable players to have ever suited up for the Montreal Canadiens. He spent his entire sixteen year NHL career with the Habs from 1973 to 1989. In 1,160 regular season games, he recorded 501 points (239 goals, 262 assists), 585 penalty minutes, and a massive +196 plus/minus rating. He then earned 73 points in 182 playoff games, helping his team win five Stanley Cups (1976, 1977, 1978, 1979 and 1986).

He was the recipient of four consecutive Frank J. Selke trophies (1978, 1979, 1980 and 1981) which is given annually to the forward who demonstrates the best defensive abilities. He was also awarded the Conn Smythe trophy in 1979 which is given annually to the most valuable player in the playoffs. He was inducted into the hockey hall of fame in 1992 and had his number 23 jersey retired by the Montreal Canadiens in 2008.

But that wasn’t the end for Gainey with the Canadiens, as he had two stints as their head coach in 2005-06 then again in 2008-09. He also served as their general manager from 2003-2010. The Canadiens missed making playoffs two of those six seasons, and when they did make it, they didn’t get past the semi-finals. Every general manager makes errors, and this list will point out the top fifteen biggest mistakes Bob Gainey made as Montreal’s general manager.

15. All 2008 Draft Picks

via Zimbio.com

via Zimbio.com

The Montreal Canadiens had five draft picks in 2008, and not one of them turned out to be a household name.

Danny Kristo (56th overall): The 26-year-old right winger has yet to make his NHL debut. He is now under contract with the Pittsburgh Penguins organization and has spent the last few seasons playing in the AHL.

Steve Quailer (86th overall): The 27-year-old right winger has not played any in NHL games. He spent a little over one season with the Hamilton Bulldogs, recording 15 points in 76 games between 2012 and 2014, but that’s as far as he got with the Canadiens organization.

Jason Missiaen (116th overall): The huge 6’8, 206 pound goaltender has not played in a NHL game. After spending three seasons in the AHL, the 26-year-old is now playing overseas.

Maxim Trunev (138th overall): The 26-year-old right winger has also never played a NHL game. This Russian native has been playing overseas in the KHL for the past several years.

Patrick Johnson (206th overall): The 27-year-old center has never seen any NHL action. After being drafted, he played four seasons with the University of Wisconsin from 2007 to 2011, followed by a short time in the ECHL and WHL.

14. Why Chipchura?

via Zimbio.com

via Zimbio.com

The Montreal Canadiens had the 18th overall pick in the 2004 NHL Entry Draft and they chose Kyle Chipchura. If the Habs were committed to getting a decent center man, they could have chosen Travis Zajac, who was drafted two picks later by the New Jersey Devils.

Chipchura ended up only playing 68 regular season games with the Canadiens between 2007 and 2009, tallying just 14 points and a -17 plus/minus rating. He was then traded in December 2009 to the Anaheim Ducks for a fourth round pick. After spending some time with Anaheim, he went on to play for the Phoenix Coyotes (currently the Arizona Coyotes) and remains with them to date.

Zajac, on the other hand, went on to excel in the NHL, spending his entire career so far with the New Jersey Devils and racking up 414 points and a +29 rating in 734 regular season games to date.

13. Not Re-Signing Kovalev

via habseyesontheprize.com

via habseyesontheprize.com

Alex Kovalev is definitely one of the best Russian players to have ever played in the NHL. During his entire NHL career, the 6’2, 220 pound right winger racked up 1,029 points in 1,316 regular season games.

It was surely an honor to have Kovalev playing for the Canadiens from 2004 to 2009. He racked up an impressive 264 points (135 of those points on the power play), 20 game-winning goals, and 871 shots on goal in 314 games.

It was certainly a shock when the Habs didn’t re-sign him, considering that during his last season with them in 2008-09, he led the team in goals (26) and points (65).

The Ottawa Senators quickly signed him and he also went on to play for the Pittsburgh Penguins and Florida Panthers.

12. Louis LeBlanc

via RDS.ca

via RDS.ca

After a disappointing 2008 draft, you’d think the Canadiens organization would have picked a better player than Louis LeBlanc for their first round choice (18th overall) in 2009.

LeBlanc went on to play 50 regular season games with the Canadiens between 2011 and 2014, earning just 10 points. He spent most of his time with Montreal’s AHL affiliate, the Hamilton Bulldogs.

After failing to earn a regular spot in the NHL, the 25-year-old center spent a short time overseas, playing for three different leagues during the 2015-16 season: HC Slovan Bratislava in the KHL; MsHK Zilina in the Slovakian League; and Lausanne HC in the Swiss League.

He then announced his retirement from professional hockey in June 2016 and plans to continue his studies at Harvard University in Boston.

11. Begin For Janik

via LaPresse.ca / via theprovince.com

via LaPresse.ca / via theprovince.com

In February 2009, winger Steve Begin was traded to the Dallas Stars in exchange for defenseman Doug Janik.

Begin began his career with the Calgary Flames before joining the Montreal Canadiens for the 2003-04 season. Although Begin wasn’t a high scoring player, he was certainly a fan favorite and definitely wasn’t afraid to throw his body around. During the five seasons he spent with the Habs, he totalled a whopping 607 hits, ranking him second among all his teammates. He was also an asset on the penalty kill, tallying 7 points, 84 hits, 64 blocked shots, and over 719 minutes of on-ice time while a man down.

Doug Janik, on the other hand, ended up playing just two games with the Canadiens. It’s not hard to figure out who the winner of that trade was.

10. Theodore For Aebischer

via nhl.com / via milehighhockey.com

via nhl.com / via milehighhockey.com

In March 2006, the Montreal Canadiens traded goaltenders by sending Jose Theodore to the Colorado Avalanche in exchange for David Aebischer.

After being drafted 44th overall in the 1994 NHL Entry Draft by the Montreal Canadiens, Jose Theodore spent the first nine seasons of his career with them, earning 141 wins (including 23 shutouts), along with a .911 save percentage and a 2.62 goals against average in 353 games. His best season was in 2002 when he was awarded two trophies: the Vezina Trophy for being the best goaltender that year, as well as the Hart Memorial Trophy for being the most valuable player of the regular season.

After the trade, David Aebischer played a total of 39 games with the Canadiens, recording just 17 wins (with no shutouts), a .898 save percentage, along with a 3.28 goals against average.

9. Not Re-Signing Yanic Perreault

via picclick.ca

via picclick.ca

After spending the first eight years of his NHL career between the Toronto Maple Leafs and Los Angeles Kings, Yanic Perreault finally found his way to the Montreal Canadiens in 2001. He spent the next three seasons with them, recording 133 points (67 goals, 66 assists) in 224 regular season games.

Among all Habs players during those three seasons, Perreault was tied for first overall on the team with 14 game-winning goals and ranked second overall in points (133), power play goals (18), power play points (40), and shots on goal (415). He also dominated in the faceoff circle with a 62.8% faceoff win percentage.

In October 2005, the Nashville Predators signed Perreault as a free agent. He spent the last three years of his NHL career with four different teams (Nashville, Phoenix, Toronto and Chicago) before retiring in 2008.

8. Trading Higgins and McDonagh

Anne-Marie Sorvin-USA TODAY Sports

Anne-Marie Sorvin-USA TODAY Sports

In June 2009, Bob Gainey made a big trade by giving Chris Higgins, Ryan McDonagh, Doug Janik and Pavel Valentenko to the New York Rangers in exchange for Scott Gomez, Tom Pyatt and Michael Busto.

Prior to the trade: Higgins was doing pretty well with the Canadiens, having accumulated 151 points in 282 games, including 56 power play points and 12 game-winning goals. Janik, however, had only played two games with the Habs, while neither McDonagh nor Valentenko had played in the NHL at that point.

After the trade: Michael Busto never played a NHL game. Tom Pyatt did play 101 games with the Canadiens in the following two seasons (2009-2011), but recorded just 12 points and a -6 plus/minus rating.

Now Scott Gomez’s circumstances were very interesting. First of all, included in the trade was also his huge contract, which had five years remaining on it and over $30 million left owed to him. Despite having decent numbers on the score sheet with 108 points 196 games, he had a disappointing -23 plus/minus rating, along with 122 penalty minutes. After playing three seasons with the Habs, it’s a good thing they bought out the remainder of his contract and sent him packing.

I do have mention Ryan McDonagh’s fantastic career thus far with the Rangers. The defenseman is currently in his seventh season with them and has racked up 193 points in 426 games. He also has an amazing +122 plus/minus rating and has not finished any season in the minuses since his NHL career has started. Not to mention the fact that he’s also their team captain. The Canadiens should have definitely held on to him.

7. Not Re-Signing Sheldon Souray

via nhl.com

via nhl.com

Sheldon Souray spent the first three years of his NHL career with the New Jersey Devils before getting traded to the Montreal Canadiens in March of 2000.

This 6’4, 230 pound defenseman was tough to miss on the ice, not to mention the fact that he had one of the hardest shots in the entire league. During his time with the Canadiens (2000-2007), he delivered 206 hits and had 258 blocked shots. He also had a whopping 810 shots on goal in 324 regular season games played, along with earning 160 points (including 89 of those points recorded on the power play).

A lot of fans were disappointed when the Canadiens didn’t re-sign Souray and he ended up joining the Edmonton Oilers in 2007. After spending three seasons with Edmonton, he then played for the Dallas Stars and Anaheim Ducks before officially retiring in 2015.

6. Traded Down For A Worse Pick

via Zimbio.com

via Zimbio.com

In June 2006, the Canadiens traded their first round pick (16th overall) to San Jose in exchange for the Sharks’ 20th pick, along with their second round pick (53rd overall).

The Canadiens ended up getting David Fischer in the first round and Mathieu Carle in the second. Fischer ended up not even playing the NHL, while Carle played just three NHL games with the Habs in 2009.

San Jose also wasn’t a big winner in the trade, as they chose Ty Wishart who didn’t even play a game with the Sharks. He played a total of 26 NHL games between the Tampa Bay Lightning and New York Islanders.

Neither one of Montreal’s choices were very good picks, considering there were a lot of other big names they could have chosen, which will be discussed after the jump!

5. Giroux, Foligno, Berglund… David Fischer?

via bleacherreport.com

via bleacherreport.com

The Montreal Canadiens had the 20th choice in the 2006 NHL Entry Draft and they claimed David Fischer. Who? Most people hadn’t even heard of him.

At the time of the draft, the 16-year-old defenseman was playing for Apple Valley High School in Minnesota. Measuring at 6’3 and 185 pounds, he never did make it to the NHL. He spent four seasons playing for the University of Minnesota, followed by two seasons in the ECHL with the Florida Everblades. He did play two games with the Houston Aeros of the AHL in 2011-12, but that was it. He has since been playing overseas.

If the Canadiens would have skipped on Fischer, they could have chosen one of the other drafted choices who turned out to be pretty big names: Claude Giroux (drafted 22nd), Patrik Berglund (drafted 25th), and Nick Foligno (drafted 28th).

4. Not Re-Signing Michael Ryder

via Zimbio.com

via Zimbio.com

Michael Ryder was first drafted by the Montreal Canadiens 216th overall in the 1998 NHL Entry Draft. He then spent the first four seasons of his NHL career with them from 2003-04 to 2007-08, earning 207 points (99 goals, 108 assists) in 314 regular season games. He was very impressive on the power play, scoring 46 of his 99 goals on the man advantage. In fact, he led the team in overall goals during two of those four seasons. Between 2003 and 2008, he also recorded the most shots on goal on the team with 813.

When his contract expired in 2008, Bob Gainey and the Canadiens organization did not resign Michael Ryder. Although his first three seasons were quite impressive, he struggled in his final year with them, having totalled 31 points in 70 games in 2007-08.

He went on to play the next three seasons with the Boston Bruins, recording 127 points (with 25 of his 63 goals scored on the power play) in 235 games, along with a +30 plus/minus rating. He also helped them win the Stanley Cup in 2011. Perhaps Gainey should have kept him, although Ryder did have another short stint with the Habs in 2012-13, tallying 21 points in 27 games.

3. Juggling Two Jobs

via bleacherreport.com

via bleacherreport.com

In January 2006, Bob Gainey fired head coach Claude Julien. Gainey then stepped in to take over his coaching duties until the end of the season. This happened again when he fired Guy Carbonneau in March 2009 and for the second time he stepped in as their temporary head coach.

During both times behind the Canadiens bench, his team totalled a record of 29 wins, 21 losses, and 7 overtime/shootout losses in 57 regular season games. They did make the playoffs during both of those seasons (2005-06 and 2008-09), but lost both times in the quarter-finals (first time to Carolina and then to Boston), recording just 2 wins and 8 losses.

It just goes to show that juggling two jobs – general manager and head coach – was just too much to handle for Bob Gainey.

2. Putting Francois Beauchemin On Waivers

Isaiah J. Downing-USA TODAY Sports

Isaiah J. Downing-USA TODAY Sports

The Montreal Canadiens drafted Francois Beauchemin 75th overall in the 1998 NHL Entry Draft. During his time with the Canadiens organization, the 6’1, 208 pound defenseman spent the majority of it with their AHL affiliate, the Hamilton Bulldogs, and played just one NHL game with Montreal during the 2002-03 season.

After his time with the Canadiens, he played for the Columbus Blue Jackets, Anaheim Ducks, Toronto Maple Leafs, and is currently a member of the Colorado Avalanche. He also helped the Ducks win the Stanley Cup in 2007.

Beauchemin has had a good career to date, playing a total of 789 NHL regular season games and earning 259 points (including 79 of them earned on the power play), along with a +14 plus/minus rating. Perhaps the Canadiens should have kept him.

1. Not Re-Signing Saku Koivu

via habseyesontheprize.com

via habseyesontheprize.com

Habs fans were in shock when fan-favorite and Canadiens captain, Saku Koivu, was not re-signed in 2009.

Chosen 21st overall in the 1993 NHL Entry Draft by the Montreal Canadiens, the Finnish center spent the first fourteen years of his NHL career with the Habs from 1995 to 2009, serving ten of those seasons as captain. He is ranked tenth overall among all Canadiens players in NHL history with 641 points in 792 regular season games. Of those 641 points, 245 of them were earned on the power play. He was also great in the faceoff circle with a very impressive 6,563 faceoff wins.

He won two awards during his time with the Canadiens. He was given the Bill Masterton Memorial Trophy in 2002 which is given annually to the player who portrays the highest quality of perseverance, sportsmanship, and dedication to the sport. He was then awarded the King Clancy Memorial Trophy in 2007 which is given annually to the player who shows leadership qualities both on and off the ice, as well as made a humanitarian contribution to the community.

After his remarkable time with the Canadiens, he spent the last five years of his career with the Anaheim Ducks before retiring in 2014.

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