White Sox general manager Kenny Williams has developed a penchant over the years for making daring, out-of-nowhere trades. His deal with Kevin Towers to bring in Jake Peavy at the 2009 trade deadline—after Peavy nixed a similar deal that May—epitomized his willingness to leave no stone unturned.

From Chicago’s perspective, the move was risky for several reasons.

Then just 2 ½ games behind the Tigers in the AL Central, the White Sox acquired Peavy, who had not pitched since June 8 and would not return for at least another month, instead of a healthy starter who could have contributed throughout the summer. In doing so, the White Sox inherited the three-year, $52 million extension Peavy signed with the Padres in 2007. The hitch did not kick in until the 2010 season, when Peavy earned $15 million, followed by a $16 million payday in 2011, and $17 million heading his way this year. Barring something unforeseen, the team will decline its $22 million option for 2013, handing the 30-year-old a $4 million buyout.

Fortunately for the White Sox, all Peavy effectively cost the team is the aforementioned money. The prospects Williams sent to San Diego—lefties Aaron Poreda and Clayton Richard, and righties Adam Russell and Dexter Carter—were highly regarded at the time, but have not amounted to much. Richard’s 1.4 WARP effort in 2010 represents the only valuable campaign any of them have produced.

And even the money might not look so bad, had Peavy not suffered an injury so rare, the surgery performed to repair it might one day be named after him.  Peavy had been worth 5.7 and 4.2 WARP, respectively, in the two seasons prior to the trade, so it was not unrealistic for Williams to expect value commensurate with the lofty salaries in his extension.  Alas, the tendon that connected the righty’s lat muscle to his humerus bone had other ideas.

All of this is significant now because the coming season is likely Chicago’s last chance to extract value from Peavy before—health-permitting—he departs in free agency.  The 18-month timeline for recovery from the surgery is up, and Peavy is as healthy as he thinks he is ever going to be.

The White Sox, on the other hand, are reeling. They may struggle to match last season’s 79-83 record, and they will almost certainly miss the playoffs for a fourth straight year. Their farm system is in shambles, with just one prospect, Addison Reed—who is likely Chicago’s closer of the future—ranking in the league’s top 101.

The best Williams and the White Sox can hope for is that Peavy stays healthy and pitches effectively over the first half of the 2012 season. Peavy’s 4.92 ERA last year was buoyed by a bloated .317 BABIP and unlucky 63.9 percent strand rate, belying his solid 3.25 FIP. Four months like that could make Peavy—who has a partial no-trade clause—a desirable rental at this year’s deadline, and perhaps enable Williams to infuse some talent into his barren pipeline.

Williams’ record with his patented blockbusters is less than stellar, but in hindsight, the Peavy acquisition may have been a shrewd move felled by misfortune. Peavy enters this spring in the best shape of his post-surgery life. If he can finally catch a break, perhaps Williams and the White Sox will too.

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