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Listomania! The 20 Worst NHL Trades of the Decade Part 2 (#10-1)

December 16, 2009, 12:47 AM ET [ Comments]

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Oh boy, the epic conclusion! Are you ready? Forget a contrived, dramatic introduction. Let's just jump right into it.

Ladies and gentleman, boys and girls, children of all ages, I present to you:

The Ten Worst NHL Trades of the Decade!

10. TORONTO BAILS ON BOYES AND 24TH PICK FOR VETERAN NOLAN

March 5, 2003

Leafs receive: Owen Nolan
Sharks receive: Brad Boyes, Alan McCauley, 2003 1st Rd. Pick (Mark Stuart)


It was the spring of 2003, and the Leafs were in pursuit of a veteran scoring presence up front with the playoffs just around the corner. They decided to ship what would prove to be a healthy ransom to San Jose for five-time 30 goal scorer Owen Nolan.

Nolan, 31 at the time, lit it up with 7-5-12 totals in the remaining 14 games of the regular season. In the playoffs however, he was a dud, as the former Shark collected no goals and two assists over seven games. The winger had 48 points in 2003-04, but missed 17 regular season games and all of the playoffs due to injury. He did not return to the NHL until 2006-07, signing on with the Coyotes.

For just 26 regular seasons goals, and one playoff round victory in which Nolan played no part, the Leafs forfeited more than they might have ever fathomed. Boyes has morphed into a 30+ goal scorer of his own, as the former 24th overall pick has 119 goals over the last four seasons (with 43 and 33 in the last two years, respectively).

The 1st round pick included in the deal eventually made it’s way to Boston (much like Boyes). The Bruins selected Colorado College captain Mark Stuart. Since becoming a full time NHL defenseman in 2007, Stuart has yet to miss a single game for the B’s. The Iron Man on the blueline has been an absolute rock defensively for Boston.

McCauley, the only player with genuine experience that departed Toronto, was no slouch during his tenure in San Jose. The Ontario native had 83 points in 174 games (20 goals in 2003-04), which was ironically the exact same total of points he had in 304 games for Toronto.

9. CAPS SHIP STRUGGLING STAR JAGR TO BIG APPLE

January 23, 2004

Capitals receive: Anson Carter
Rangers receive: Jaromir Jagr


With the Washington Capitals on their way to missing the playoffs for the second time in three seasons, they decided to part ways with underperforming megastar Jaromir Jagr. Jagr had been a bit of a disappointment in Washington. Gone were his 100+ point seasons, replaced by a pedestrian point-per-game performance from a star seemingly giving a lackluster effort.

Many presumed the 32-year-old Czech winger was cooked, and so the Capitals dumped him and his lofty salary ($11 million per year, tops in the NHL) to the Rangers in exchange for familiar forward Anson Carter. As part of the deal, the Caps agreed to pay more than 1/3 of Jagr’s salary.

Carter, at the time, had just 17 points on the year for New York (in 43 games). He recorded 10 points in 19 games for Washington before being shipped off to Los Angeles that same season.

While the Caps got 10 points from Carter and Jared Aulin (who never made it out of the AHL with their organization) out of the deal, the Rangers got a key cog to their post-lockout resurgence. After missing the playoffs for seven straight seasons, New York qualified for the postseason thanks in large part to Jagr’s 123 point campaign in 2005-06.

Narrowly edged out by Joe Thornton for both the Hart and Art Ross Trophies, Jagr captured the Lester B. Pearson Award for his magnificent season. Before electing to join the KHL for the 2008-09 season, Jagr racked up 319 points in 277 games over 3+ years in the Big Apple. In three postseason appearances, the man with 1599 career points boasted a 10-17-27 line in 23 games for New York.

While Carter was busy playing for six teams over three NHL seasons, Jagr was helping to carry an Original Six franchise back to respectability.

8. FLAMES HAND DUCKS FUTURE CONN SMYTHE WINNER GIGUERE

June 9, 2000

Flames receive: 2000 Rd. 2 Pick (Matt Pettinger)
Ducks receive: Jean-Sebastien Giguere


Nothing like giving up an eventual Conn Smythe Trophy and Stanley Cup winning goaltender for beans, right? Well, that’s precisely what went down back in June of 2000 when the Flames shipped former 13th overall pick Jean-Sebastien Giguere to the Mighty Ducks of Anaheim for a mere 2nd round draft pick.

Giguere, taken in the first round by the Whalers in 1995, was just 23 at the time of the trade. He had just 30 games under his belt at the NHL level, stuck behind Fred Brathwaite and one over-the-hill goalie or another (Grant Fuhr, Ken Wregget) in Calgary.

The Flames decided to send the pick to Washington, getting Miika Elomo and a 4th rounder (Levente Szuper) in return. Neither ever played a single shift for Calgary.

Giguere, meanwhile, went on to capture the Conn Smythe Trophy in a losing effort in 2003 against the New Jersey Devils. In 2007, he helped backbone the Ducks to their first ever Stanley Cup championship. He is now 29 appearances shy of his 500th NHL game, with a 214-173-25-36 record through his first 471 contests (including 32 shutouts).

In 52 career playoff games, Giguere is 33-17 with a sparkling 2.08 GAA and .925 Sv%. He has six career postseason shutouts.

7. PANTHERS MAKE BOYLE A BOLT

January 7, 2002

Panthers receive: 2003 5th Rd. Pick
Lightning receive: Dan Boyle


Undrafted defenseman Dan Boyle was in his fourth season with the Florida Panthers when he was abruptly sent to Tampa Bay in January of 2002. The former collegiate standout at Miami (Ohio) had yet to breakout with the struggling Panthers, so the organization shipped him off in exchange for a 5th rounder in the 2003 draft.

Since then, Boyle has finished in the top ten in points among defenseman on four occasions (in six NHL seasons), emerging as one of the premier offensive defenseman in the game. Boyle appears well on his way to his 5th 50+ point campaign since 2002-03, as he currently has 28 points in 34 games. Since departing the Panthers, the 5’11 blueliner has 338 points in 504 games for both Tampa Bay (where he won a Stanley Cup in 2004) and the San Jose Sharks.

Martin Tuma and Dan Travis were both selected by Florida in round 5 of the 2003 draft. As is almost always the case on this list, neither player ever suited up for an NHL team.

6. FLAMES NOT SO SAVVY IN TRADE FOR ZAYNULLIN

November 15, 2002

Flames receive: Ruslan Zaynullin
Thrashers receive: Marc Savard


How many more goals would Jarome Iginla have if Marc Savard, presuming he still morphed into the player he is today, had been feeding him the puck for the last seven years? Probably even more than the impressive total he ended up with.

25-year-old center Marc Savard was struggling to the tune of 1-2-3 totals in 10 games in 2002-03 for the Flames. After a disappointing 2001-02 campaign, Calgary decided to sever ties with the talented pivot. They shipped him to Atlanta for Ruslan Zaynullin, the 34th overall pick by Tampa in 2000 who had bounced from the Bolts to the Coyotes to the Thrashers in just two calendar years.

All the while, Zaynullin had yet to come over from Russia, where he was playing at the time with Kazan Ak-Bars. Unfortunately for the Flames, Zaynullin never gave hockey a try in North America. Zaynullin, soon-to-be 28, is now a member of Balashikha MVD HC in the KHL.

As for Savard, you know full well how things turned out. Since the trade, he has racked up 472 points in 439 games for the Thrashers and Bruins. He has been a fixture in the top 10 in points, and in the top 5 in assists since the lockout. He has emerged as a leader and a team player, dramatically improving his defensive game since Claude Julien arrived in Boston.

With back-to-back All Star game appearances, and 19 points in 18 playoff games for Boston, Bruins fans should be thankful the Flames failed to discover his elite talent. Luckily they were blinded by the wonder that was Ruslan Zaynullin, a future scrub of the Kontinental Hockey League.

5. PANTHERS DEAL LUONGO TO ‘NUCKS FOR BROKEN BERT, SPARE PARTS

June 23, 2006

Canucks receive: Roberto Luongo, Lukas Krajicek, 2006 Rd. 6 Pick (Sergei Shirokov)
Panthers receive: Todd Bertuzzi, Bryan Allen, Alex Auld


For five seasons, goaltender Roberto Luongo stood on his head for the Florida Panthers and had little to show for it. Despite his top notch Sv% year-after-year (including .931 in 2003-04), the Panthers failed to qualify for the postseason with Luongo between the pipes.
After turning down a 5-yr offer from Florida, Luongo was shipped in a blockbuster deal to the Vancouver Canucks. He immediately inked a 4-yr, $27 million dollar deal upon arriving.

Since the swap, Luongo has gone 130-74-22 for Vancouver, twice guiding them to the second round of the playoffs in his first three full seasons. He has yet to finish a season with a GAA above 2.40 or a Sv% below .917. He is the backbone, the difference maker and above all the captain of the Canucks franchise. Despite all of his success, Luongo is still just 30-years-old.

Bertuzzi was the flop of all flops in Florida. Bert had four points on opening night for the Panthers. Unfortunately, it was all downhill from there. He played in just seven games before succumbing to injury, and by the time he was ready to come back, the Panthers had decided they no longer needed him around. Bertuzzi was then sent to Detroit, as the Red Wings hoped for a scoring boost from the rugged winger.

Auld, after having a respectable season as the starter in Vancouver, struggled for the Panthers. He finished 2006-07 with a .888 Sv% and 7-13-5 record before moving on to Phoenix.

Bryan Allen has been the only serviceable return for the Panthers, and that’s despite missing 80 games last year due to injury. He has six points in 32 games in 2009-10 for the Panthers, the only remaining part of the six player deal for Florida.

4. PENGUINS TRADE FACE OF FRANCHISE FOR BAG OF PUCKS

July 11, 2001

Penguins receive: Kris Beech, Ross Lupaschuk, Michal Sivek
Capitals receive: Jaromir Jagr, Frantisek Kucera


Fire sales happen all the time in sports, and never were they more prevalent in hockey than in the years leading up to the lockout. When you ship out a superstar to save some coin, you have to wind up with something to show for it. Whether it’s a young NHLer with potential or a promising prospect, you can’t walk away empty-handed. If you do, you wind up on lists like these. Oh hey, Pittsburgh Penguins of 2001! Welcome aboard!

After the 2000-01 season, during which Mario Lemieux returned from retirement, Jagr was thanked for his 121 point season then promptly jettisoned to the Washington Capitals. With five 40+ goal seasons in six consecutive 95+ point seasons (including 62-87-149 in 1995-96), Jagr left town as the reigning Art Ross Trophy winner.

You’d think someone like that would fetch a King’s Ransom. You thought wrong. Way wrong.

Kris Beech potted 10 goals in 2001-02 and never did squat for most of the rest of his playing days (25 total goals in 198 games for various teams over eight seasons). Ross Lupaschuk played in all of three NHL games for the Penguins before heading to the SEL. Michal Sivek had three goals in 38 games in 2002-03 for Pittsburgh. He has been with Sparta Praha in the Czech League since 2004-05.

All in all, the Penguins got a whopping 13 goals in return for, at the time, the most dynamic player in the sport of hockey. That same dynamic player who still had 207 goals and 313 assists left in the tank. As they say, you can’t win ‘em all, but you can’t lose them all quite as badly as this.


3. MILBURY SENDS LUONGO AND JOKINEN TO PANTHERS ON DRAFT DAY

June 23, 2000

Islanders receive: Oleg Kvasha, Mark Parrish
Panthers receive: Roberto Luongo, Olli Jokinen


They don’t call him Mad Mike for nothing! On the day of the 2000 draft, Mike Milbury traded away Kevin Weekes to Vancouver, then sent prized prospect Roberto Luongo and Olli Jokinen, a player he’d acquired for former Isles star Ziggy Palffy, to the Florida Panthers for Oleg Kvasha and Mark Parrish. The move preceded the Islanders selecting Rick DiPietro with the 1st overall pick. It was, at the time, the stupidest thing Milbury had ever done.

Milbury picked Luongo 4th overall in 1997, and gave up on him with just 24 NHL games under his belt. Jokinen had 21 points in 82 games at the age of 21 during his lone season on the Island. He and Luongo, as you well know, were on their way to future All Star seasons, team captaincy, Vezina candidacy, you name it.

Kvasha and Parrish, on the other hand, were well on their way to continued mediocrity. Kvasha never topped 15 goals in five seasons with New York, peaking in 2003-04 with 51 points. He was an absolute dud in the playoffs, with a 1-2-3 line in 17 postseason games. Kvasha now suits up for Mytishchi Atlant in the KHL.

Parrish fared better, with four 20+ goal seasons including a 30-30-60 campaign in 2001-02. He’s bounced around since then, playing for the Kings, Wild and Stars, and is now a member of the Norfolk Admirals (Tampa Bay’s affiliate) in the American Hockey League.

While, unlike many of the net returns on the list, Milbury did get some production out of Kvasha and Parrish, saying the price he paid was steep would be the understatement of the decade. Well, almost. There are still two more trades to come and, as you may have guessed, Milbury’s contributions to this list don’t end here.

2. SHARKS ROB BRUINS BLIND IN THORNTON TRADE

November 30, 2005

Bruins receive: Wayne Primeau, Brad Stuart, Marco Sturm
Sharks receive: Joe Thornton


Very rarely does an NHL organization trade away its captain. In most cases, that particular player is used heavily in the team’s marketing plan and beloved by fans. Not to mention, the “C” on his sweater embodies the organization’s confidence in his abilities as both a player and a leader. That, simply, is why they are moved so infrequently.

That brings us to the Boston Bruins, a team that has often defied logic and common sense throughout the last quarter century. In March of 2000, the B’s shipped Ray Bourque to Colorado so he could win a cup. Just 20 months later, Jason Allison, who replaced Bourque as captain, was sent to Los Angeles after holding out in the early part of the 2001-02 season.

Boston managed to go two full NHL seasons without trading away their appointed leader, but got anxious 23 games into the post-lockout era. General Manager Mike O’Connell sent fan favorite Joe Thornton, who had 33 points at that point in 2005-06, to San Jose. For Marleau? Nabokov? Try Primeau, Stuart and Sturm. Talk about getting hosed. Thornton was still 26 at the time, had a 101 point year and two 35+ goal seasons on his resume, and was emerging as one of the top centers in the National Hockey League.

O’Connell tore the fanbase’s heart out, and replaced it with a 4th line mucker, middle-pairing defenseman and a streaky winger.

Thornton, whose playoff futility has been well documented, has 432 points in 338 games for the Sharks. At the conclusion of the season he was traded, the Ontario native was awarded the Art Ross Trophy as leading scorer and Hart Trophy as league MVP.

Primeau, if I remember correctly, scored a nice goal against the Flyers once. Other than that, he was virtually useless in Boston. Stuart seemed mildly promising but scoffed at the thought of remaining a Bruin. He and Primeau were packaged together and sent to Calgary for Chuck Kobasew and Andrew Ference.

Sturm is the only leftover from the original swap, and is on pace for his 4th 20 goal season in five years for Boston (after missing 63 games in 2008-09 due to injury). The German LW scored, arguably, the greatest goal in recent Bruins’ history, as he netted the GWG in game 6 of the 2008 postseason matchup with the Canadiens.

However, such a feat pales in comparison to everything Thornton has done since the deal went down four calendar years ago. Boston is left with the consistently inconsistent Sturm, and the oft-injured Ference. The Sharks? Jumbo Joe leads the entire league in both assists and points in 2009-10.

1. MILBURY COUGHS UP CHARA AND SPEZZA FOR ENIGMATIC YASHIN

June 23, 2001

Islanders receive: Alexei Yashin
Senators receive: Bill Muckalt, Zdeno Chara, 2001 #2 Overall Pick (Jason Spezza)


Its official, folks: June 23rd is hereby declared Mike Milbury day. When you decide to celebrate this occasion, don’t be too surprised if your Isle loving friends don’t want to partake in the festivities. Exactly one year after the aforementioned Luongo and Jokinen for Kvasha and Parrish swap, Milbury one-upped himself in the summer of 2001.

The Islander’s delirious general manager sent Bill Muckalt, Zdeno Chara and the 2nd overall pick to the Senators for the enigma that was Alexei Yashin. Yashin had a heap of talent, but his behavior off the ice was nauseating for the Sens. He was often accused of dogging it on the ice, and repeatedly demanded more money, something he was adamant about deserving. It culminated in Ottawa suspending Yashin for the entirety of the 1999-00 season.

And this was Milbury’s guy? This was the kind of personality he coveted? Someone so greedy he missed a year of hockey? So selfish he was stripped of his captaincy? You bet!

Milbury instantly inked Yashin to an absurd 10-year, $87.5 million dollar deal. After underperforming in his five seasons on Long Island, Yashin was bought out. The Islanders will continue to pay him until the end of the 2014-15 season. That’s a full eight years after his last game for the organization. Only in America, right?

Milbury, clearly, grossly misjudged Chara’s talent. Big Z was a rock for the Senators, and a large part in many of their playoff runs. He has received Norris Trophy nominations in back-to-back years with Boston, capturing the award last year for the first time in his career.

Spezza, the consensus #2 pick at the time behind Ilya Kovalchuk, has racked up 437 points in 434 games for the Senators. Spezza dominated the OHL, and success at the NHL level seemed like a foregone conclusion. Well, except to Milbury apparently. The 26-year-old center has 39 points in 40 playoff games, including 22 in 20 contests during Ottawa’s run to the finals in 2007.

While the point-per-game center and Norris winner they traded away play on elsewhere, the Islanders can look forward to paying Yashin $4.75 million next season alone, followed by four consecutive years at $2.20 million annually.

Never has a trade wreaked havoc as profoundly on an organization’s future as this deal did. For that, I’m tipping my cap to Mr. Milbury, the orchestrator of the worst trade of the decade in the National Hockey League. Cheers, Mad Mike!

JC

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