Buyer's remorse? Five worst recent deadline deals, White Sox edition

The White Sox have had success adding pieces at the trade deadline, but it's maybe arguable they've had more failure making deals under duress. Here are the five worst July trades since 2000:

5. July 25, 2002: Traded Ray Durham and cash to the Oakland Athletics. Received Jon Adkins.

Durham was set to be a free agent at the end of the year and a July nosedive had taken the Sox from four games back in the AL Central in late June to 14 games behind Cleveland when Durham was traded.

Not wanting to sign the then-30-year-old Durham to a big contract, but determined to get something for him, the Sox took a flyer on Adkins. Which might have made sense if not for the fact that under baseball's last collective bargaining agreement, the Sox could have offered Durham arbitration and either gotten him to agree to an affordable one-year contract, or gotten draft pick compensation when he signed with another team.

The Sox might have been better off with that draft pick than watching Adkins flounder to a 5.08 ERA in just less than 80 innings in his Sox career. Sox fans probably would have more enjoyed another two months of Durham's under-appreciated career.

4. July 28, 2012: Traded Eduardo Escobar and Pedro Hernandez to the Minnesota Twins. Received Francisco Liriano.

Liriano was walking one of the valleys of an up-and-down career with the Twins, but as a left-hander with good velocity, he seemed like a good candidate to improve under the tutelage of Sox pitching coach Don Cooper.

Instead of recapturing the dominant form he had flashed at times since his rookie year, Liriano kept nibbling at the strike zone, walking too many batters and giving up home runs at inopportune times. Deciding they'd done all they could do with him, the Sox let Liriano walk in the offseason only to watch him have a resurgent year that helped carry Pittsburgh to the playoffs for the first time in more than two decades.

Liriano probably wouldn't have found that success in the American League, or without a ballpark that helps hide some of his flaws. And the Sox probably don't miss Escobar or Hernandez. It was still a disappointing outcome as Lirano's struggles were part of the reason a division title slipped through the Sox's fingers.

3. July 26, 2001: Traded James Baldwin and cash to the Los Angeles Dodgers. Received Jeff Barry, Gary Majewski and Onan Masaoka.

The Sox predictably got little for Baldwin, who like Durham was set to be a free agent after the season in which he was traded. Unlike Durham, Baldwin wasn't very good.

What makes this trade embarrassing for the Sox is that they didn't actually want Jeff Barry, a journeyman minor league first baseman. They wanted pitching prospect Jonathan Berry.

Berry never made the majors, otherwise this would have been an embarrassment that could have lived on for years and years.

2. July 27, 2011: Traded Edwin Jackson and Mark Teahen to the Toronto Blue Jays. Received Jason Frasor and Zach Stewart.

Instead of trading their best asset near the deadline, the Sox basically bundled it with Teahen's ill-advised contract for salary relief, plus the meh and bleh performances they'd respectively get from Frasor and Stewart.

Jackson certainly had value as the Jays immediately spun him off in a package for Cardinals center fielder Colby Rasmus. In a way Rasmus has been a hitting version of Jackson, with his up-and-down career that hasn't seen him reach his full potential. Though it's no doubt Rasmus' line with Toronto (.233/.295/.431) would make a number of Sox outfielders over the last three years envious.

No matter how crowded their rotation was at the time, or if Rasmus or someone similar would have been available in a similar package, the Sox should have done much better in any deal with Jackson while he was near the peak of his value.

1. July 30, 2010: Traded David Holmberg and Daniel Hudson to the Arizona Diamondbacks. Received Edwin Jackson.

Jackson graces the list twice, coming and going. Even though Jackson had one the better stretches of his career with the Sox (3.66 ERA over 196 2/3 innings), it was an awful idea to trade the young Hudson for him straight up, much less adding another prospect in Holmberg.

The Sox were concerned Hudson's fly ball tendencies wouldn't play in their ballpark. They were frustrated that he nibbled at the plate in his brief audition with the big club. And they were worried he would get hurt.

The injury concerns were validated when Hudson needed elbow surgery during the 2012 season, and then needed another during his comeback attempt. Still, he pitched to a 3.58 ERA over 347 innings for the Diamondbacks (who also play in a homer-friendly park) before his injuries. He also did it for nearly league minimum salaries.

Besides not getting good value back in Jackson, it was rumored the Sox had only traded for him in an attempt to pry Adam Dunn away from the Washington Nationals. When Nats GM Mike Rizzo either backed out, or the Jackson-for-Dunn swap wasn't as solid as Sox GM Kenny Williams had believed, the Sox were stuck with Jackson and ended up claiming Manny Ramirez off waivers in August to bolster their offense instead.

All of this was to help hold on to an unlikely division lead grabbed after an unreal 26-5 stretch during June and July. And the Sox did lead as late as Aug. 8, but the reinforcements didn't really matter much as the team slid to a double-digit deficit by mid-September. 

That the Sox were willing to spend big bucks to keep their run alive in 2010 only made it more frustrating when they punted in 2011 just to save a few bucks they never would have had the need to spend if they'd kept Hudson around.