Greg Wyshynski | December 17, 2009
(No, the first decade of the 21st century doesn’t technically end until 2011. Save your bellyaching. But we’ve had nine NHL seasons and one stolen from us since 1999-2000, and Yahoo! Sports has decided it’s time to rank the best and worst of the last "decade." Enjoy, and snark freely in the comments.)
We know what you’re thinking: Will there be a separate list for the trades Mike Milbury wasn’t involved in?
Sure, the former New York Islanders GM appears multiple times on the following countdown of the most lopsided trades of the last decade. It’s also not exactly a spoiler alert to say that Joe Thornton(notes) appears on the list, too. But in looking back at the biggest fleecings of the 2000s, there were some epically wrongheaded moves that don’t ensure either Mad Mike or Jumbo Joe end up at the top spot.
In assessing these deals, we were looking at what was known about the players involved at the time; the motivations behind the trade; the impact on the respective teams and, in hindsight, the level of talent that actually changed hands.
For example, we were tempted to put the trade of Robert Lang(notes) to the Detroit Red Wings on this list because it resulted in the Washington Capitals getting Tomas Fleischmann(notes) and eventually drafting Mike Green(notes). But Lang had a couple of Lang-like years for Detroit while the Capitals found an all-star at the bottom of the first round. So it’s not the complete whiff some that some of these other gems are.
Here are the 10 most lopsided trades of the last decade …
10. Atlanta Thrashers trade Marian Hossa(notes) and Pascal Dupuis(notes) to the Pittsburgh Penguins for Angelo Esposito(notes), Colby Armstrong(notes), Erik Christensen(notes) and a first-round draft pick (Daulton Leveille). (Feb. 26, 2008)
There were plenty of questions about the Penguins giving too much here for a rental. Kevin Dupont, writing on NBC Sports, was weary of the deal:
They gave up a lot of equity, in terms of player talent, for what could be a very short-term rental. That’s right, all of 127 days from acquiring Hossa, and giving up the likes of Angelo Esposito, Colby Armstrong, Erik Christensen and a first-round draft pick, the Pens could see him walk out of town for good, and for little more than a handshake as he gets into the cab to take him to the airport.
Well, Hossa ended up doing just that … but he also had 26 points in 20 playoff games to help the Penguins to the conference title. Dupuis is still thriving for Pittsburgh.
As for the Thrashers, they’ve seen Esposito bust with injuries, they traded Christensen and watched Armstrong become an offensive enigma. The pick, Daultan Leveille, is still playing for Michigan State.
9. Atlanta Thrashers trade Braydon Coburn(notes) to the Philadelphia Flyers for Alexei Zhitnik(notes). (Feb. 24, 2007)
Another masterpiece from Don Waddell, GM of the Thrashers. Coburn was a 21-year-old rugged defenseman who wasn’t getting solid ice time. Zhitnik, 34, started the season on the Islanders, was traded to the Flyers and shipped to the Thrashers.
Coburn would soon develop into one of the league’s best two-way defensemen, especially after being teamed with Kimmo Timonen(notes). Zhitnik was a mega-bust for Atlanta, tallying eight points in 65 games the following season before getting his contract bought out. He’s now the captain for Dynamo Moscow in the KHL.
8. Buffalo Sabres trade Chris Gratton(notes) and a 2004 fourth-round pick (traded to Edmonton, who drafted Liam Reddox(notes)) to the Phoenix Coyotes for Danny Briere(notes) and a 2004 third-round pick (Andrej Sekera(notes)). (March 10, 2003)
Gratton’s been passed around so much in his NHL career that he’s eligible to be the punch line of a Sean Avery(notes) locker room joke.
In 2002-03, he had 44 points in 66 games for the Sabres before the Coyotes came calling; he had one point in 16 games for Phoenix after the trade, followed up 29 in 68 games the next season. He was eventually traded to the Colorado Avalanche in a deal for Keith Ballard(notes) and Derek Morris(notes); Colorado also acquired a pick that would become Paul Stastny(notes). Ouch.
Briere went on to become a 90-point player for the Sabres, albeit briefly.
7. Philadelphia Flyers traded Patrick Sharp(notes) and Eric Meloche(notes) to the Chicago Blackhawks for Matt Ellison(notes) and a 3rd round selection in 2006. (Dec. 5, 2006)
Now, this could have easily been the Blackhawks stealing Kris Versteeg(notes) from the Boston Bruins in exchange for Brandon Bochenski(notes) in 2007. But Flyers Goal Scored By … offers compelling evidence that this is the bigger fleecing:
After two good seasons playing in Hockey East, Sharp turned pro and joined the Phantoms for what would have been his junior year in college. The next season he split time between the Flyers and Phantoms pretty evenly, and the during the lockout he helped the Phantoms win the Calder Cup with 21 points in 21 playoff games after a 53 point regular season. And then when Sharp finally looked ready for the big leagues Bobby Clarke made one of the bigger mistakes of his tenure and traded him away for a guy that is now in the KHL and a third round pick that we then traded to Montreal for two other picks, who turned out to be current Phantom Jonathan Matsumoto(notes) and busted goalie Jakub Kovar.
[...]
He’s exactly the kind of guy you want sitting next to you on the bench, which is the type of guy the Flyers have traditionally tried to acquire, not tried to deal away for a Guns ‘n Roses poster and half used phone card.
Especially when it’s a poster for "Chinese Democracy."
6. New York Islanders trade Roberto Luongo(notes) and Olli Jokinen(notes) to the Florida Panthers for Mark Parrish(notes) and Oleg Kvasha. (June 24, 2000)
There are going to be people who believe this trade should be much, much lower on the list, and we get that. But bear with us.
Luongo was 20 years old and had played 24 games for the Islanders at the time of the trade, which is to say he wasn’t ROBERTO LUONGO yet. Jokinen was 21, on this second NHL franchise and hadn’t cracked 30 points yet. Trading both players were egregious errors in judgment that will haunt Mike Milbury’s career as an NHL executive. But the real mistake was committing to Rick DiPietro in the draft when there was already a goalie many felt was a future star in the system.
But the reason this isn’t closer to Numero Uno is that Parrish and Kvasha weren’t exactly Matt Ellison-level busts for New York. Parrish became a 30-goal scorer during five productive seasons on the Island. Kvasha was a serviceable player for five seasons, too. In hindsight, it’s ridiculously lopsided. But in context, it’s not as bad as any of the top five.
5. Boston Bruins trade Joe Thornton to the San Jose Sharks for Marco Sturm(notes), Wayne Primeau(notes) and Brad Stuart(notes). (Dec. 1, 2005)
Like this trade, for example. Thornton was bitter after becoming a scapegoat for the team’s disappointing play in 2005, traded to the Sharks after signing a contract extension with the Bruins. Nothing like anger as a motivator: He had 92 points in 58 games for the Sharks that season, winning the Hart Trophy and establishing himself as an elite center during his time in teal.
There’s no question Sturm (27) and Stuart (26) were important pieces for the Sharks. But Bruins GM Mike O’Connell failed to get an impact player on the level of Thornton or a blue-chip prospect; settling for a bunch of complementary pieces at a lower cost.
In the interest of equal time, Eric McErlain’s post on the post-Thronton Bruins; resurgence puts the real impact of this trade in a different light:
Consider for a moment that Thornton hadn’t been traded. Without the deal, there’s no free agent cash for Savard and Chara, and in the case of the latter, perhaps we should ask Boston goalie Thomas what sort of contribution the 6′9" Slovak defenseman makes to keeping the team’s goals against per game the best in all of hockey (2.00).
Normally, I’m not a fan of trading a quarter for two dimes and a nickel, but you have to be impressed with how the franchise parlayed the return from the Thornton trade into a number of serviceable players. For starters, ex-Shark Marco Sturm is the same player he’s always been, a steady two-way forward good for nearly 30 goals per season.
Fair points. But still a bum deal.
4. Pittsburgh Penguins trade Jaromir Jagr(notes) and Frantisek Kucera to the Washington Capitals for Kris Beech(notes), Michal Sivek, Ross Lupaschuk(notes) and future considerations. (July 11, 2001)
The hindsight on this one is interesting, as Jagr requested a trade from then-General Manager Craig Patrick for the betterment of the franchise, as he felt the team could use the salary they spared to sign other vital players like Alex Kovalev(notes). He also thought he was bluffing.
Patrick didn’t, evidently.
But no matter how Jagr was traded, the return for arguably the biggest star in the League at that point was nothing short of putrid. Beech became a journeyman. Sivek played 38 games in the NHL; Lupaschuk played three.
Still, Craig Patrick remained high on these bums even after Jagr moved on to the Rangers. From the Post Gazette:
Beech — "He’ll have a good career ahead of him. … He understands the game defensively a lot better than he did when he first turned pro."
Lupaschuk — "I think he’s doing fine. … I like the way he’s coming along. He’s got a great skill level."
Sivek — "His progress has been stunted a little bit, but we definitely see him as a prospect to play in the National Hockey League."
Not everyone who has followed the pro careers of Beech, Lupaschuk and Sivek shares Patrick’s upbeat perspective. In Wilkes-Barre, the talk is of Beech’s inconsistency, of the way Lupaschuk’s offensive game has deteriorated while his defensive work remains suspect, of Sivek’s lackluster work ethic.
Score one for the downbeat. Now, there will be some who believe the 2004 trade of Jagr for Anson Carter(notes) belongs here, too. But that was a cash dump that freed the Washington Capitals from Jagr’s sullen mood and contract while helping the Rangers. From CBC Sports:
Speculation had New York and Washington close to completing a trade last July, then resuming talks in November. At the time, however, Jagr reportedly was reluctant to waive the $11 million US option year on his current contract.
Under the terms of this deal, the Capitals will pay $20 million of the $44 million remaining on Jagr’s seven-year, $77-million contact. The Rangers will pay the rest.
Not nearly as lopsided a deal that the initial trade was, no matter Jagr’s output in D.C.
3. New York Islanders trade Zdeno Chara(notes), Bill Muckalt and first-round pick in 2001 Draft (Jason Spezza(notes)) to the Ottawa Senators for Alexei Yashin(notes). (Nov. 9, 2001)
From CBC Sports:
Islanders GM Mike Milbury, meanwhile, has made a deal that could salvage his managerial reputation, which has been damaged by a series of ill-advised trades, in landing an elite impact player entering the prime of his career – or he could have saddled himself with a big headache while passing up on one of the best prospects to come out of Canada in some time.
If you guessed ‘B’, congratulations.
Senators fans had turned on Yashin after he demanded a trade and sought to renegotiate his contract after seemingly every season. The franchise no longer considered him a cornerstone. Chara was a hulking defenseman with raw talent. Spezza was as blue-chip a prospect as they come.
The Islanders? They decided to build around a player with undeniable offensive flourish (40 goals, 88 points in the season before the trade) but one whose attitude could rightfully be questioned. Then they gave him a contract that still counts against their cap while he toils in the KHL.
Forget the transfer of talent between the teams; the Islanders’ misguided commitment to Yashin earns this a lofty place on the list.
2. Calgary Flames trade Marc Savard(notes) to the Atlanta Thrashers for Ruslan Zainullin. (Nov. 15, 2002)
The placement of this trade on the list can be summed up in two words: "Ruslan Zainullin."
Forget that Savard became one of the best pivots in the NHL, collecting assists like frequent flier miles for the Thrashers and the Bruins. The fact is that the Flames moved a promising, NHL-level asset for a player originally drafted by the Tampa Bay Lightning who never left Russia for the NHL.
Granted, the Flames were in a tough spot because Savard had been feuding with Coach Greg Gilbert. Then again, Gilbert was fired two weeks after the trigger was pulled on this deal. Whoops.
1. Florida Panthers trade Roberto Luongo, Lukas Krajicek(notes) and a sixth-round pick (Sergei Shirokov(notes)) to the Vancouver Canucks for Alex Auld(notes), Bryan Allen(notes) and Todd Bertuzzi(notes). (June 24, 2006)
A trade made on the eve of the NHL Draft, it’s the worst deal in the history of hockey.
That’s not our assessment. That’s what then-Florida Panthers GM Jacques Martin said about the trade in a 2007 radio interview, a claim he refused to back down from. Who are we to argue with that expertise?
Again, there were no illusions about the goaltender Roberto Luongo was at that time or the one that he would become. Just like there were none about the miles on Bertuzzi’s body as a 30-year-old power forward, who ended up playing an astoundingly bad seven games for the Panthers as the centerpiece of this trade.
No contest: It’s the most lopsided trade of the decade.
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Tags: Alex Auld, Alex Kovalev, Alexei Yashin, Alexei Zhitnik, Andrej Sekera, Angelo Esposito, Anson Carter, Atlanta, Atlanta Thrashers, Bill Muckalt, Bobby Clarke, Boston, Boston Bruins, Brad Stuart, Bryan Allen, Buffalo Sabres, busted goalie, Calder Cup, Calgary Flames, Canada, Captain, Chris Gratton, coach, Colby Armstrong, Colorado, Colorado Avalanche, Craig Patrick, Danny Briere, Derek Morris, Detroit, Detroit Red Wings, Don Waddell, Edmonton, elite impact player, Eric McErlain, Eric Meloche, Erik Christensen, Executive, Florida Panthers, Frantisek Kucera, general manager, goalie, Greg Gilbert, hockey, impact player, Jacques Martin, Jakub Kovar, Jason Spezza, Joe Thornton, Jonathan Matsumoto, Keith Ballard, Kevin Dupont, Kimmo Timonen, Kris Beech, Liam Reddox, Lukas Krajicek, Marc Savard, Marco Sturm, Mark Parrish, Matt Ellison, Matt Ellison-level, Michal Sivek, Mike Green, Mike Milbury, Mike O'Connell, Montreal, National Hockey League, NBC, New York, New York Islanders, nhl, Oleg Kvasha, Olli Jokinen, Ottawa Senators, Patrick Sharp, Paul Stastny, Philadelphia Flyers, Phoenix, Phoenix Coyotes, Pittsburgh, Pittsburgh Penguins, player, Rick DiPietro, Robert Lang, Roberto Luongo, Ross Lupaschuk, Ruslan Zainullin, Russia, same player, San Jose Sharks, Sergei Shirokov, serviceable player, Tampa Bay Lightning, Todd Bertuzzi, Tomas Fleischmann, United States, USD, Vancouver Canucks, Washington, Washington Capitals, Wayne Primeau, Yahoo!
As a small boy, the first thing about this great sport that grabbed me was the passion of the game, he passion of the players, players who show that they just don’t seem to have the capacity to play at half speed, be it pre-season, regular season, or playoffs. The passion of the fans that find a way to be there, supporting the boys, letting anyone know who they root for with a full-throated fury. The passion of the professionals in the broadcast booth and the front office who are constantly sharing their love for a game that not everyone understands.
Much more embarrassing was the case of 
No. 1 Star: 
Writing about attendance woes this season is tricky. First, because NHL teams in many U.S. cities traditionally see a spike after the New Year, as tickets are gifted for the holidays and the games gain more vitality; but mostly because in the battle of putting food on the table in a horrible economy and paying $300 for a regular season hockey game, thwarting starvation wins.
When he was invited to Team Canada’s orientation camp in August, 
