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Baseball's biggest trade deadline busts

With baseball's non-waiver trade deadline fast approaching Saturday, Astros pitcher Roy Oswalt(notes) and Nationals first baseman Adam Dunn(notes) are among the prominent players expected to change addresses before the week is out, joining the recently dealt Cliff Lee(notes) and Dan Haren(notes). For contenders, diving into the trade market at deadline time usually means financial risk: giving up talented, inexpensive youth and taking on a high salaried player who can help a potential playoff push over the final two months.

Sometimes it works out, sometimes it doesn't. The Yankees have pulled off some good deadline deals over the years, bagging David Cone in 1995 and Aaron Boone(notes) in 2003, among other coups. Cone became a vital piece of five playoff clubs while Boone earned a spot in Yankee history with one swing against Boston's Tim Wakefield(notes) that won Game 7 of the 2003 American League Championship Series. But as the saying goes, sometimes the best trades are the ones that don't get made. The trades featured on our list of the biggest trade deadline busts should serve as a warning to GMs with itchy trigger fingers.

Last year the Detroit Tigers, contending in the American League Central, swung a deal with the Seattle Mariners for $9.9 million pitcher Jarrod Washburn(notes). He bombed big time, with a 7.33 earned run average and 1-3 record in eight starts, as the Tigers were nosed out of the playoffs by the Minnesota Twins.

Seattle was on the opposite end of a one-sided deal back in 1997, when they were so enamored with Red Sox reliever Heathcliff Slocumb that they parted with top young players Jason Varitek(notes) and Derek Lowe(notes) to get him. The Mariners did make the playoffs that year, though they were bounced out quickly in the first round. And Slocumb, whose $3 million salary represented a premium price for a reliever at the time, was of little help during his one-plus seasons in Seattle, going 2-9 with an earned run average close to 5.00. Lowe and Varitek ultimately became heroes of the Red Sox 2004 championship team.

[Photos: Players on the trading block: Adam Dunn | Roy Oswalt | Cliff Lee | Dan Haren]

To compile our bust list we looked at trades for high-priced veterans. We then looked at how much salary each brought, what they cost in return, how they performed after the deal, and whether the new team achieved its goal of a post-season berth (which goes a long way in paying back the added salary the team took on). So not every trade that's been famously panned over the years makes the list.

For example, the 1987 Tigers bolstered their pennant push by acquiring veteran pitcher Doyle Alexander from Atlanta. In return, they sent the Braves minor league pitcher John Smoltz(notes), who went on to a brilliant 20-year career that may land him in the Hall of Fame. But the deal did for the Tigers what it was supposed to do. Alexander, whose $650,000 salary was high but not over the top for its day, went 9-0 in 11 starts, leading a late charge past Toronto for the AL East division crown. He then won 14 games the next season, when the Tigers lost the division to Boston by one game. Losing out on Smoltz for the long haul was a steep price, but the Tigers were so weak during much of the 1990s and early 2000s that his presence may not have brought the club a playoff appearance anyway. The idea: When you have the chance now, go for it.

Of course, that means risking the trade blowing up on you. The Toronto Blue Jays, contending for the playoffs in 2000, decided to beef up their pitching with Texas' Esteban Loaiza(notes). He wound up going 5-7 down the stretch and 25-28 over two-plus seasons while making $11 million. The player the Jays gave up, Michael Young(notes), has been one of the league's top hitters for the past eight years. The Jays are still looking for their first playoff birth since 1993.

Then there are the 2005 San Francisco Giants, who made a deadline deal with the Seattle Mariners in which they gave up talented young catcher Yorvit Torrealba(notes) for outfielder Randy Winn(notes), who had three-plus years and $29 million left on his contract. Winn, a corner outfielder, never drove in more than 65 runs for the Giants, who finished 75-87 that year and failed to make the postseason during Winn's tenure. Sometimes, it's just better to sit tight.

The list:

Jarrod Washburn to the Tigers: Slideshow
Heathcliff Slocumb to the Mariners: Slideshow
Randy Winn to the Giants: Slideshow
Carlos Baerga to the Mets: Slideshow
Harold Baines to the Rangers: Slideshow
See more bad deals

In Pictures: Baseball's biggest trade deadline busts