Veteran Larry Murphy was rejuvenated in Detroit, where he was paid by Toronto to win a Cup that continues to elude the Leafs. Tom Pidgeon/Getty Images

4. Toronto trades Larry Murphy to Detroit for future considerations (March 18, 1997).

The Leafs looked at this deal as a tender mercy. The aging Murphy had become a favorite target of the local boo-birds, and his minutes were dwindling as his effectiveness declined. But the deal to Detroit added wings to his feet, as well as to his sweater, and he became an integral part of back-to-back Cup winners.

The Leafs side of the deal? They agreed to pay part of Murphy's salary. Hard to believe that Toronto hasn't won a Cup in 40 years considering that kind of solid asset management.

3. Philadelphia sends Alexei Zhitnik to Atlanta for Braydon Coburn (Feb. 25, 2007).

It might be a little early to put the stamp on this one, but the early results look disastrous for the Thrashers, a team that saw a certain playoff berth slipping away after a blazing hot start. Zhitnik was looked upon as a steady, physical presence for the blueline, but he's been a major -- and expensive --disappointment since arriving in Blueland.

Coburn, on the other hand, looks to be developing into exactly the type of player the Thrashers hoped they'd be getting out of Zhitnik. His learning curve this season has been startling, and many observers have labeled him as Philly's best defender. Coburn soaks up more than 20 minutes a night, and his plus-12 rating is second best on the team.

2. Boston trades Geoff Courtnall, Bill Ranford and future considerations to Edmonton for Andy Moog (March 8, 1988).

Desperate to upgrade their goaltending in an effort to break a 16-year Cupless streak, the Bruins anted up for Moog. But to get the proven veteran, they had to give up two of their top youngsters...and the deal ended up biting them hard.

Though Moog teamed up with Reggie Lemelin to lead the Bruins to the Finals the following year against his old team, it was Ranford who stole the show. The Oilers netminder was given the Conn Smythe after holding his ex-mates to just eight goals as Edmonton won the Cup in five games.

The Penguins got a meager return indeed on Alek Stojanov, considering who they gave up to get him. And his NHL career lasted all of 107 games. AP

1. Pittsburgh trades Markus Naslund to Vancouver for Alek Stojanov (March 20, 1996).

When fans talk about the most lopsided trades of all time, this one's always in the mix. Despite being almost a point-per-game player that season, Naslund was perceived by the Pens as soft and incapable of reaching his potential. Stojanov, a hulking, 6-4, 232-pound winger, was seen as a better fit. The seventh overall pick in 1991, he was fearless in the corners and a willing combatant who'd be the perfect complement for Pittsburgh's Euro-heavy lineup.

Unfortunately, he had less hockey sense than a bag of pucks, and lasted just 45 games with the Pens. Naslund has gone on to score more than 800 points in Vancouver, where he's also served as captain for seven seasons.