In terms of high stress jobs, being a general manager of a professional sports team has to be a rather difficult one. Think about it: your quality of work is done, out in the open, for pretty much all to see. It is constantly critiqued, on television, radio, in print and on the World Wide Web. Plenty of people declare that, when you’ve done a horrible job, that they could have done it better! I mean, they won first place in their fantasy sports league, so clearly they know what they are doing, right? Because we all know that fantasy sports are a superb indicator of real world skills! But, with that in mind, one of my personal favorite professional sports is ice hockey. Make the right moves as your teams general manager and fans in your city of employment love you. Bring them a Stanley Cup Championship? You drink for free for the rest of your life. But screw up? Trade the wrong guys away? You will be vilified, and eventually fired.
Now, sometimes, the trade is so obviously bad, getting rid of the bumbling general manager is an easy decision. However (and unfortunately for fans of those franchises) too often these horrid GMs don’t just get to make one bad trade before they are axed. No, in many cases, it wasn’t one bad trade, but rather several bad trades that led to the eventual pink slip. So, with that in mind, let’s take a crack and identify some of the worst trades made by some of the most inept general managers. These are trades that, over time, lead to their terminations. We will try to single out that one fateful trade that their team’s fans all tend to point to as “that trade” that ultimately resulted in their dismissal.
15 GM: Jay Feaster - Calgary Flames
The Trade: Jay Bouwmeester For Like, a Bag of Pucks
I will say it now, and could say this for most entries on the list: there will be a trade made in most GM’s careers where they just can’t get anything close to equal value for a player. Maybe the guy has baggage, or the general manager just lacks leverage, but it happens, even to the best ones in the world. And Jay Feaster? He was not one of the best in the world, but he certainly did make one of those lopsided trades. He sent Jay Bouwmeester packing, and unless you happen to be a fan of Bouwmeester or related to one of the guys who was traded for him, odds are you won’t recall who went back to Calgary in return. That’s a telling sign right there, but he’s not alone - plenty of GMs in all sports have done it. But, for Feaster, trades like that one meant he had to get his resume together so he could find employment elsewhere.
14 GM: Floyd Smith - Toronto Maple Leafs
The Trade: Tom Kurvers For a First Round Draft Pick
Sometimes, you trade a draft pick for a player and no one benefits. Sometimes, you trade a pick for a player and the player is better than the pick. And then, sometimes the draft pick is far better than the guy you traded for. This is a case of that. Tom Kurvers was OK. Nothing special, nothing really awesome. Just OK. And, you don’t trade first round draft choices for just OK players. Especially not when you are the Toronto Maple Leafs, and the first round selection you are trading away is a really high one, because your team is God awful at that point in time. Like, they were so bad they were at risk of “earning” the number one selection, and they traded it away. And here’s where it really gets painful for Maple Leafs fans. What draft was that pick in? Oh, that was just the draft class headlined by Eric Lindros. And who did that pick turn into? Blueline anchor Scott Niedermayer. Suffice it to say, Smith only lasted two seasons as GM.
13 GM: Dave Nonis - Vancouver Canucks
The Trade: None
Wait, what? Isn’t this list about the trades the general manager got fired for making? Why yes, yes it is. But, it’s my list, and there do deserve to be exceptions every now and then. And in the case of Dave Nonis, there certainly appears to be a case for such an exception. How so? Because during a trade deadline, one which his roster was begging for an infusion of some hired guns to push them not just into the playoffs, but deep into the playoffs, he kicked the tires on several of the top prizes. And he landed NONE of them. Now, sometimes you can say you are thankful that a GM, for whatever reason, did not make a trade (thus meaning he held onto a talented player). This is not one of those times, because the Canucks badly needed some help, and he got them no one. But, for that effort, he did find himself unemployed.
12 GM: George McPhee - Washington Capitals
The Trade: Semyon Varlamov for Draft Picks
If there is one hard truth in many professional sports, it’s that draft picks tend to be over-valued. This is probably less true in hockey than in other sports, but it’s still applicable. Teams love to have lots of draft picks for really one reason-it’s a crap shoot, so the more picks you have, the better your chances of landing a keeper are. But, for every diamond in the rough you find, there are three or four career minor leaguers coming your way. And there’s the issue with McPhee’s trade. Varlamov at the time looked to be a rising star between the pipes, but the Capitals had depth and wanted to use the depth to fix other needs. Problem is, none of the picks actually really panned out (and in fact, a couple of those choices were eventually flipped for other disappointments). In defense of McPhee, he had been in his post so long that the move may not have been that bad, so much as it was a clear indication that it was his time to go.
11 GM: Jim Rutherford - Philadelphia Flyers
The Trade: Justin Williams to Carolina
Take it from me, folks. As a Flyers fan, I hated the day we traded away Justin Williams, and he’s reminded me of that painful trade several times over. If you have Williams, and you trade him away, you will regret it. It’s just the way it goes. Now, in fairness, trades are a part of hockey, and sometimes a guy like him seems expendable, or maybe he had yet to develop and some scout in the front office convinced the general manager that he was never going to develop (or that the player being offered in trade had a better upside). But, anyone who was saying that in relation to Williams would have been pretty wrong. Rutherford had a couple other stinkers on his resume too, so it wasn’t all about Williams -but, just like Justin did for Carolina as they pushed for Lord Stanley’s Cup, he proved vital in LA’s Cup runs too. Rutherford actually stepped down, but he just sped up the inevitable.
10 GM: Pierre Gauthier - Montreal Canadiens
The Trades: Jaroslav Halak and Michael Cammalleri
I must at least start off with a modest defense of the decision to trade Halak, even though I have it as a trade that cost him his job. That defense? Like the issues Vancouver had with Schneider and Luongo, the Canadiens found themselves blessed with Carey Price and Jaroslav Halak. And Halak was coming off a hot playoff run, so his value should have been off the charts. But, Gauthier pegged Price to be the smarter long term play, so he sent Halak packing - but got nothing notable in return. If the decision to move on from Halak wasn’t bad enough, there’s more. Gauthier also later traded away star Michael Cammalleri for a middling return. Those kinds of moves get you to the point where you don’t get to make trades anymore.
9 GM: Darryl Sutter - Calgary Flames
The Trades: Dion Phaneuf, Olli Jokinen
Life is just unfair for Calgary Flames fans, isn’t it? Not one, but two general managers making this list should tell you all you need to know about how that franchise has been struggling. In the case of Sutter, he made blunder after blunder. Two things should jump out. First, in the trade section, we’ve called out not one, but two trades. And second? That neither trade was worth pointing out the garbage that the Flames got back in return. Seriously, it was that bad. Phaneuf will always have his critics, but he’s a decent enough offensive defenseman. Those guys are invaluable in the NHL. And then, if trading away Phaneuf for basically nothing wasn’t bad enough, he sent Jokinen and Brandon Prust off to New York. Again, for nothing worth talking about. In his defense, Sutter wasn’t actually fired, but officially stepped down. Considering the moves he had made, I don’t think he was expecting to be kept around, so he just bailed early.
8 GM: Dave Taylor - Los Angeles Kings
The Trade: Rob Blake for Adam Deadmarsh
Now, in fairness, Deadmarsh had had a really nice career. Key word? Had. As in, he was not in his prime when the then-LA Kings GM sent Rob Blake away for him. Here’s a free lesson, boys and girls. Actually, two. First? Never, ever, trade away a franchise, once in a lifetime type defenseman. Rob Blake was pretty much that kind of player. And two? If you DO have to ignore rule one, for any reason, understand that you are pretty much NEVER getting anything close to equal value coming back your way. Sometimes these guys get annoyed or tired of playing on your team and they have to go. A good GM will take lemons and make lemonade. Taylor couldn’t. And his dismissal was, in all honesty, not just due to Blake’s trade. Nope. Taylor also sent guys like Olli Jokinen and Kimmo Timonen out of town, too.
7 GM: Steve Tambellini - Edmonton Oilers
The trade: Erik Cole for Patrick O’Sullivan
Honestly, Tambellini gets a spot on this list predominantly for the draft issues. Yes, I know I said this is all about the trades (specifically, the bad ones). But the draft debacles in Edmonton merit inclusion regardless. But, fortunately for me (and unfortunate for Edmonton Oiler fans), Tambellini wasn’t just bad at drafting, he was bad making trades too. I know Erik Cole has been a productive hockey player, and someone you’d like on your team. I couldn’t tell you a thing about O’Sullivan unless I busted out the search engine. When you factor in bad drafts and bad trades, it’s no wonder he lost his job. Now, in some respects, we can’t completely kill him for the drafts, because some may have been lacking in star power up top… but when you draft at or near the top of the first round so much, and you still haven’t turned things around? Yes, you are going to lose your job.
6 GM: Darcy Regier - Buffalo Sabers
The Trade: Brian Campbell to San Jose
Honestly, Darcy was probably much worse on drafting and in free agency. He made some incredibly bad choices in those areas, and those moves alone would have justified his termination. But, since this one is all about the trading action, look no further than Brian Campbell to San Jose. First glaringly obvious sign that this trade sucked for Buffalo? No mention of the returning compensation. That screams “bad trade” each and every time. Like, whomever they got in return wasn’t just bad, they weren’t even worth remembering. Ouch. But there is hope, Buffalo fans. The last few years have been better, landing some primo talent via drafts and trades, but none of that thanks to Darcy, who was dismissed.
5 GM: Paul Holmgren - Philadelphia Flyers
The Trade: James Van Riemsdyk for Luke Schenn
I am, admittedly, a Philadelphia Flyers fan. And while Homer was a fan favorite as a player, his hiring was unfortunately another one of those oh-so-typical Flyers moves to employ home grown talent that burns the franchise. This was not the only bad player personnel move that Holmgren can take credit for. It just happens to be one I consider to be his defining moment of failure. That move that made you say “he has to go”. Now, in all honesty, he did have some good ones (he wasn’t a flash in the pan). But the only thing Schenn and JVR had in common was their high draft position. Schenn looked only OK in his time in Toronto, and he never really showed anything that would have made anyone suspect he’d turn into a top pair defender. And when you trade away a budding power forward for that? One whom fans liked, and which has been a position of need? You will be torched for it, and Holmgren was.
4 GM: Mike Gillis - Vancouver Canucks
The Trades: Roberto Luongo and Cory Schneider
I am sorry to any of my readers who are fans of the Vancouver Canucks. To have been able to say at one point that your number one goalie was Roberto Luongo, and that he was backed up by Cory Schneider? That is flat out incredible depth. Like, there’s no two ways about it. That’s the kind of depth you only get to see in an All Star Game, but the Canucks had it on a nightly basis. By all accounts, Schneider was the preferred choice to remain in Vancouver, but try as he might, Gillis could not find a taker for Luongo. So, he found a taker for Schneider instead, and got a rather weak return for the stud goalie. Yes, it was a top ten pick in the draft, but it turned into no one special. This move becomes even worse when, less than a year later, Gillis then dealt away Luongo too. He needed to only deal one, but instead in the span of twelve months he had both goalies change their addresses. Considering how hard a position it is to find those number one guys for, Gillis managed to have two starters and traded them both away for basically nothing. He got fleeced, and you have to believe how he handled those two trades had a lot to do with his dismissal.
3 GM: Brian Burke - Toronto Maple Leafs
The Trade: Phil Kessel for two first round draft picks
Now, some on this list will be criticized because they got draft picks in return and those picks amounted to nothing. Toronto fans only wish that were the case with Burke. For starters, fans had reasons to be optimistic-Burke had done wonderful jobs in Vancouver and Anaheim, helping the Ducks win a Cup. But he stunk it up in Toronto, with no move being worse than the trade for Kessel. Don’t get me wrong, Kessel has been a good-to-great player in the league, but Boston had Burke ship them not one, but two first round draft picks for Kessel. And those picks? Those picks became Dougie Hamilton and Tyler Seguin. I don’t care how good Kessel is, if I was given a choice of Kessel or a pair of Hamilton and Seguin, the majority of people will take the pair, and rightfully so.
2 GM: Jack Gordon - Vancouver Canucks
The Trade: Barry Pederson for Cam Neely
Officially, this was a trade resulting from Vancouver signing Pederson as a restricted free agent. But the move went down as Pederson to Vancouver, and Neely, along with a compensation pick in the first round (which turned into Glenn Wesley) to Boston. At the time, this might have looked OK. I mean, in fairness, Pederson had had several very good years based on his statistics, and he was comparable to some of the top young players in the league. But, the ups were pretty much all before he had to undergo shoulder surgeries. Boston had soured on him and opted to move on, and the rest, as they say, is history. While Gordon wasn’t immediately escorted from the building, history was not kind on this trade. Looking back on it now, you would have had to had serious issues to sign off on that trade.
1 GM: Mike Milbury - New York Islanders
The Trade: Zdeno Chara and #2 Overall Draft Pick (Jason Spezza) for Alexei Yashin
The hardest part of this selection was actually deciding which move was the worst. I am just being honest, ladies and gentlemen. As far as general managers go, Mike Milbury may actually go down in the sports history books as one of the worst ever. Not in hockey, but in ANY sport. I’m serious. Look at his decisions, from trades to draft choices to contracts-there was not a single area of the team-building decision process that he didn’t mess up at least a few times. But Chara and Spezza for Yashin was extremely bad. We can honestly even leave Spezza out of the discussion. Chara, throughout his career, has been one of the most imposing defensemen in the NHL. And, he’s had an exceptional career to boot. Yashin was hard to figure-sure, he had the physical tools to be a great player, but he never put it all together. Even a straight-up Chara for Yashin move would have been panned now, but the fact that he felt Yashin was worth more than Chara so he tossed in Spezza? Stunningly horrible move.