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Top 10 Worst General Managers in NHL History

The duties of NHL general managers have changed throughout history. Years ago, many of them took on the dual role coach and GM while in the modern era we have general managers dishing out a lot of responsibilities to one or more assistants. But basically, a GM’s job is still to take care of the club’s day-to-day operations, make trades, sign free agents, and handle the drafting of players, etc. Like all professions, some of them are good at their job while others leave a lot to be desired.

However, even the worst GMs have their good days too. Of course, the object of the job is to make as many moves as possible that improve the franchise. Every GM in history has made positive moves along the way, but there are others who take backwards steps or make moves which don’t really have any affect at all on their squads. In this list we’re going to focus on GM’s who have done more harm than good to their teams during their stints with them.

Some of the GMs are well-known misfits while others may actually be regarded as being good at their jobs. A good GM needs to make shrewd decisions and improve his club by exchanging weak players for better ones. It takes a lot of skill to get a first-line player in return for a third-liner, but anybody can trade away their best player for another team’s top performer.

In addition, the salary cap has allowed fans to see who the smartest GMs are since they now have to have a solid plan in place when it comes to assembling a winning team within a strict budget. We’ve seen some GMs perform miracles with one club and then destroy their next club due to ineptness. These are the top-10 worst general manager stints in NHL history.

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10 Gord Stellick, Toronto Maple Leafs

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Since the Leafs haven’t won the Stanley Cup for about 50 years they could dominate this list, but we’ll just focus on a few of them. No offence to Gord Stellick, but he was really nothing more than a glorified office assistant when Harold Ballard handed him the GM job in April of 1988. Stellick was gone about 19 months later due to a series of bad moves. The most infamous was the trading of speedy forward Russ Courtnall to the arch enemy Montreal Canadiens for enforcer John Kordic and a sixth-round draft pick. Courtnall retired with 744 career points in 1,097 games while the late Kordic had 35 points in 244 contests along with 997 PIM. Stellick also dealt Al Secord to the Flyers for a fifth round pick and Miroslav Frycer to Detroit for Darren Veitch. In addition, Stellick drafted Steve Bancroft, Scott Thornton and Rob Pearson all in the first round from the nearby Bellville Bulls in 1989. Names he passed on in that draft included Bill Guerin, Stu Barnes and Adam Foote.

9 Punch Imlach-Toronto Maple Leafs

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Former Leafs coaching hero Punch Imlach returned to run the team from 1979 to 1981 when Harold Ballard rehired him. Unlike his previous tenure in Toronto (as coach), this stint didn't go so well. Imlach was hated by his players as he took several of them to court to stop them from participating in a penalty-shot competition for a television show called ‘Showdown’. He also wanted to stamp his authority on the team by getting rid of captain Darryl Sittler, whom Imlach believed wielded too much power in the dressing room and who incidentally was the prime player involved in the ‘Showdown’ dilemma. Since Sittler possessed a no-trade clause in his contract, Imlach tried to hurt him by trading away Sittler’s winger and best friend Lanny McDonald to the Colorado Rockies along with Joel Quenneville for Wilf Paiement and Pat Hickey. Paiement was then traded a couple of seasons later for Miroslav Frycer. Imlach also traded Paul Gardner and Dave Burrows for Kim Davis and Paul Marshall along with Pat Boutette for Bob Stephenson and Dave Hutchison for Pat Ribble.

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8 Gerry McNamara-Toronto Maple Leafs

Gerry McNamara was in charge of the Leafs from 1981 to 1988 and miraculously made the playoffs four times in seven seasons with a winning percentage of just .367. His draft choices were actually pretty good as he picked up Wendel Clark, Al Iafrate, Russ Courtnall, Todd Gill, Vince Damphousse, Gary Leeman and Luke Richardson. However, he dealt away Darryl Sittler to Philadelphia for Rich Costello, Ken Strong and a second-round draft choice and traded a first-round pick to New Jersey, which turned out to be Scott Niedermayer, for Tom Kurvers. He also traded Bob McGill, Steve Thomas and Rick Vaive to Chicago for Ed Olczyk and Al Secord. Secord was then shipped out for a fifth-round draft pick a couple of years later.

This is the same GM who sent John Anderson packing for Brad Maxwell and then traded Maxwell for a fifth-rounder. He acquired Larry Landon for Gaston Gingras, John Gibson and Bill Harris for Ian Turnbull and a fifth-rounder for Pat Hickey. The Leafs never had one winning campaign under McNamara and finished the 1984-85 season 32 games below .500 with just 20 wins. McNamara’s squad had one win in their past 22 games when he was fired.

7 Mike Gillis, Vancouver Canucks

THE CANADIAN PRESS/Darryl Dyck

Mike Gillis was Canucks GM from 2008 to 2014, but he seemed to lose any direction over the course of a year between 2011 and 2012. He was named GM of the year for 2010-11 and went downhill from there. The Canucks looked to be set in net for years to come with veteran Roberto Luongo and upstart Cory Schneider sharing the crease, but after Gillis’s bumbling he ended up with neither of them. He also traded Mike Brown for Nathan McIver, Shane O’Brien for Ryan Parent, Micheal Grabner, a first round pick and Steve Bernier for Victor Oreskovich and Keith Ballard and Cody Hodgson for Zack Kassian. Gillis also offered an aging Mats Sundin $20 million over two years and let top defenceman Willie Mitchell join Los Angeles as a free agent. Gillis overpaid for free agents Manny Malhotra and Marco Sturm and fired head coach Alain Vigneault in May of 2013. He then pulled a baffling hire, tabbing John Tortorella as Vigneault's replacement. Torts was a terrible fit for the Canucks and was axed after one season in which the Canucks missed the postseason. Gillis was the first to go about three weeks earlier in April, 2014.

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6 Glen Sather, New York Rangers

Kirby Lee-USA TODAY Sports

Glen Sather’s Rangers have been successful recently, but that wasn’t always the case under the controversial GM. Sather had a habit of throwing good money at mediocre players in the past and critics say the only reason he’s stopped doing so is because of the salary cap. Sather paid millions for players who were past their prime such as Scott Gomez, Wade Redden, Michael Rozsival, Darius Kasparitus, Bobby Holik, Eric Lindros and Pavel Bure.

He did the same with Chris Drury and Brad Richards and ended up buying out their contracts. Sather’s on this list because he put together some pretty bad teams when clubs were able to spend as much as they liked. He’s been with the Rangers since 2000 and failed to make the postseason in his first four seasons. Sather drafted Hugh Jessiman in the first round in 2003 while Mike Richards, Zach Parise, and Ryan Getzlaf were available. Jessiman was the only first rounder that year to never play an NHL game. He also traded Adam Graves to the San Jose Sharks for Mikael Samuelsson and sent Rangers legend Brian Leetch to the Toronto Maple Leafs for a couple of no-names in Jarkko Immonen and Max Kondratiev. Robbing the Canadiens of Ryan McDonagh and prying Rick Nash out of Columbus have helped strengthen his image, but his 14-year track record has many more negatives than positives.

5 Doug MacLean, Columbus Blue Jackets

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Doug MacLean managed Columbus from 2000 to 2007, failed to make the playoffs once, and compiled a record of 172–258–62 for a less-than-mediocre winning percentage. MacLean acquired aging players such as Sergei Fedorov and Adam Foote and signed them to big contracts when they were well past their prime. He lost a couple of good players in Tyler Wright and Francois Beauchemin in the process. MacLean drafted Gilbert Brule sixth overall in 2005 and then tried to rush him straight into the NHL. The youngster ended up suffering a pair of serious injuries before he was sent back to junior hockey.

Brule played a total of 146 games for Columbus before moving on. To think, the Jackets could've had Marc Staal or Anze Kopitar. His worst trades included Anson Carter for a fifth-round pick, Geoff Sanderson for a third-rounder, Mike Sillinger for Darryl Sydor and then trading Sydor for Alexander Stitov, and Travis Green for a sixth-rounder. MacLean also failed to re-sign free agent Ray Whitney who was one of the team’s top scorers.

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4 Bobby Clarke, Philadelphia Flyers

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Flyers legend Bobby Clarke served two stints as the team’s GM from 1984 to 1990 and from 1994 to 2006. While he built some pretty good squads there, his main weakness was goaltending during the last six years of his reign. Clarke never seemed to realize the club needed a top goalie if it was going to win a Stanley Cup and went through over a dozen goalies in his second stint in Philly.

Some of his worst trades include Michal Handzus for Kyle Calder, Dennis Seidenberg for Petr Nedved, Jeremy Roenick for future considerations, Danny Markov for a third-round pick, Dmitry Yushkevich for a seventh-rounder, Kent Manderville for Bill Tibbetts, Dean McAmmond for a fourth round-pick, Kevin Stevens for John Slaney, John Vanbiesbrouck for a fourth-rounder, Kevin Dineen for a third and seventh-round pick, Paul Coffey for a fifth-round pick, and Patrick Sharp for Matt Ellison. Yes, that Patrick Sharp.

3 Russ Farwell, Philadelphia Flyers

Russ who? Many fans may not remember Russ Farwell, but he was the GM of the Flyers from 1990 to 1994 with the team missing the playoffs each season. He led them to a mediocre record of 136-150-42 while in charge and will go down in infamy for one particular trade. In 1992, Farwell dealt Ron Hextall, Peter Forsberg, Mike Ricci, Steve Duchesne, Kerry Huffman, Chris Simon and $15 million in cash plus draft picks to the Quebec Nordiques for the rights to Eric Lindros. Even though Lindros could eventually be inducted into the Hall of Fame, he wasn’t worth the price Farwell paid. The Nordiques ended up in Colorado and Forsberg, who is in the Hall of Fame by the way, helped them win their first Stanley Cup. Farwell also went through three head coaches during his tenure and eventually lost his job at the end of the Flyers’ dismal 1993-94 campaign.

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2 Rejean Houle, Montreal Canadiens

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Rejean Houle was in charge of the Canadiens between 1995 and 2000 and a lot of Habs fans believe he was nothing short of a disaster. Houle made more than his fair share of bad trades with the worst being Patrick Roy and team captain Mike Keane to the Colorado Avalanche for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko. He also shipped out power forward Mark Recchi to the Philadelphia Flyers in exchange for Dainus Zubrus as well as sending Pierre Turgeon and Craig Conroy to the St. Louis Blues for Shayne Corson and Murray Baron.

In addition, he failed miserably on draft days by using up first round picks on the likes of Ron Hainsey, Jason Ward, Matt Higgins, Marcel Hossa and Eric Chouinard. He also dealt a top-10 pick to the New York Islanders for an over-the-hill Trevor Linden. Houle had a bad habit of shipping out veterans such as Vincent Damphousse and Recchi who were temporarily struggling rather than letting them work their way out of their slumps. In a roundabout way the Flyers basically received Recchi, John Leclair, and Eric Desjardins for Zubrus along with a couple of draft picks. The Habs team of 2000 was just a shell of what it was in 1995 when Houle took over from Serge Savard. This was due to Houle’s misguided trades, bad draft choices and lack of quality free-agent signings.

1 Mike Milbury, New York Islanders

We could write a book on Mike Milbury’s worst deals while he was GM of the New York Islanders since there were so many of them. But we’ll stick to his worst gaffes while he was in control of the team’s destiny from 1995 to 2005. At one time or another Milbury had Wade Redden, Bryan Berard, Bryan McCabe, Zdeno Chara, Darius Kasparaitis, Eric Brewer, Tommy Salo, Roberto Luongo, Olli Jokinen, Tim Connolly, Raffi Torres and Todd Bertuzzi on his roster while they were promising youngsters or in their prime. However, Milbury managed to trade away all of them.

Some examples of Milbury’s lack of patience include Roberto Luongo and Olli Jokinen being sent to the Florida Panthers for Oleg Kvasha and Mark Parrish as well as a 2nd overall pick (Jason Spezza) and Zdeno Chara for Alexei Yashin. Milbury also dealt a third-round draft choice, Bryan McCabe and Todd Bertuzzi to Vancouver for Trevor Linden. He then shipped Linden out 15 months later for a first-round pick which Milbury wasted on Branislav Mezei with the 10th overall selection. Milbury went through five head coaches during 10 seasons in charge, made the playoffs three times and handed Yashin a long-term deal which the Islanders eventually bought out. Looking at that core, you're talking about a potential dynasty that Milbury disposed of for over a decade of mediocrity. He's the blueprint for GM's learning what not to do.

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