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
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?
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
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
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.