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Good, bad and ugly: A look back at memorable NHL trade deadline deals

Brian Burke is fond of saying that NHL general managers make more mistakes at the trade deadline than the rest of the year combined.

It's a testament to the chaotic nature of last-minute negotiations and the misguided decision-making that can occur when the pressure is ramped up. The GMs most likely to err are the ones trying to add pieces for a run at the Stanley Cup because prices are high and only one team is presented with the trophy in June.

With this season's trade deadline set to pass on Monday afternoon, here's a look back at five deadline moves that paid off for contenders since the 2004-05 lockout and five that didn't:

Five To Remember

March 9, 2006: Mark Recchi traded to Carolina Hurricanes by Pittsburgh Penguins for Niklas Nordgren, Krys Kolanos and Carolina's second-round choice in 2007 draft (later traded to San Jose, later traded to Philadelphia—Philadelphia selected Kevin Marshall).

Breakdown: The Hurricanes were a surprise team coming out of the lockout and GM Jim Rutherford recognized that he had an opportunity with the deadline approaching. Sensing the need for forward depth, he paid what looked like a heavy price to acquire Recchi. The veteran would go on to score seven goals in a post-season that would net Carolina its first Stanley Cup.

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Feb. 26, 2008: Brad Stuart traded to Detroit Red Wings by Los Angeles Kings for second-round pick in 2008 draft (later traded to Colorado—Colorado selected Peter Delmas) and fourth-round pick in 2009 draft (later traded to Atlanta—Atlanta selected Ben Chiarot).

Breakdown: At the time, Red Wings GM Ken Holland was picking up what he thought was a rental player in Stuart. But the defenceman ended up playing a key role in the team's Stanley Cup victory and was rewarded in the summer with a four-year contract extension. He continues to play in Detroit.

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Feb. 26, 2008: Marian Hossa and Pascal Dupuis traded to Pittsburgh Penguins by Atlanta Thrashers for Colby Armstrong, Erik Christensen, Angelo Esposito and Pittsburgh's first-round pick in 2008 draft (Atlanta selected Daultan Leveille).

Breakdown: This remains one of Ray Shero's signature moves even though it didn't net the franchise a Stanley Cup. The deal went down just minutes before the deadline and provided Sidney Crosby with a top-flight winger in Hossa, who finished third in playoff scoring that spring. While Detroit would go on to beat Pittsburgh in a six-game final, the Penguins gained experience that helped them return the favour a year later. To this day, Dupuis remains a Penguin.

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March 4, 2009: Bill Guerin traded to Pittsburgh Penguins by New York Islanders for third-round pick in 2009 draft (later traded to Phoenix—Phoenix selected Michael Lee).

Breakdown: Shero got it right with this veteran acquisition. Playing alongside Crosby, Guerin scored five goals down the stretch and added another seven in the playoffs. However, his most important contribution was the steadying presence he provided to a team of young stars, particularly when it fell behind Detroit in the Stanley Cup final before rallying to win in seven games.

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Feb. 17, 2011: Chris Kelly traded to Boston Bruins by Ottawa Senators for second-round pick in 2011 draft (Ottawa selected Shane Prince).

Feb. 18, 2011: Rich Peverley and Boris Valabik traded to Boston Bruins by Atlanta Thrashers for Mark Stuart and Blake Wheeler.

Breakdown: Buoyed by acquiring Kelly a day earlier, Bruins GM Peter Chiarelli kept up his wheeling-and-dealing a little over a week from the deadline by landing Peverley as well. It was exactly the boost Boston needed to end the franchise's Stanley Cup drought. The depth was useful as the playoffs wore, especially after Nathan Horton was knocked out of the final series against Vancouver with a concussion.

Five To Forget

Feb. 24, 2007: Alexei Zhitnik traded to Atlanta Thrashers by Philadelphia Flyers for Braydon Coburn.

Breakdown: The Atlanta Thrashers were on their way to the first—and only—playoff appearance in franchise history so GM Don Waddell was in the mood to gamble. It didn't pay off. The 35-year-old Zhitnik would only play a season and a half for the Thrashers while Coburn has gone on to become a key member of the Flyers blue-line. The best part? He's still just 26 years old.

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Feb. 26, 2008: Brian Campbell traded to San Jose Sharks by Buffalo Sabres along with a seventh-round draft pick in 2008 (San Jose selected Drew Daniels) for Steve Bernier and San Jose's first-round pick in the 2008 draft (Buffalo selected Tyler Ennis).

Breakdown: Campbell was one of the big fish available at the 2008 deadline and GM Doug Wilson had to surrender a pretty big package to get him. The smooth-skating defenceman put up great numbers for the Sharks, but couldn't save them from an early playoff exit. He then signed with Chicago as a free agent in the summer. Ennis, meanwhile, has since become a regular with the Sabres.

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Feb. 26, 2008: Brad Richards traded to Dallas Stars by Tampa Bay Lightning along with Johan Holmqvist for Jussi Jokinen, Jeff Halpern, Mike Smith, and a fourth-round draft pick in 2009 (later traded to Minnesota, later traded to Edmonton—Edmonton selected Kyle Bigos).

Breakdown: The Lightning were a few years removed from their Stanley Cup victory and facing some financial uncertainty, making it necessary for one of Richards, Martin St. Louis or Vincent Lecavalier to go. Richards ended up being the odd man out and GM Jay Feaster dealt him for a package of players. Five years later, none of the group is still in Tampa.

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March 4, 2009: Justin Williams traded to Los Angeles Kings by Carolina Hurricanes for Patrick O'Sullivan and a second-round pick in 2009 (Carolina selected Brian Dumoulin).

Breakdown: After watching Williams endure a string of injuries, the Hurricanes decided to part with one of the core members of their 2006 Stanley Cup team. O'Sullivan wouldn't make much of an impact in Raleigh, but Williams continues to be a 60-point player for the Kings. Los Angeles rewarded him with a four-year extension last February.

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Feb. 28, 2011: Dustin Penner traded to Los Angeles Kings by Edmonton Oilers for Colten Teubert and Los Angeles' first-round pick in 2011 draft (Edmonton selected Oscar Klefbom)

Breakdown: Time is running out for Penner to make this deal look a little better—he had just eight goals in his first 69 games as a member of the Kings. While it remains to be seen if Teubert and Klefbom develop into regular NHLers, it's safe to assume Los Angeles GM Dean Lombardi expected more from Penner. In fact, with another trade deadline approaching, he's still looking for a winger who can score.

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