The White Sox finished 16 games behind the Tigers in the AL Central last season and 12 games shy of the Rays for the wild card. Their farm system was one of the shallowest in baseball coming into the 2011 campaign, so there aren’t any immediate reinforcements to propel the ChiSox back into contention. A wholesale rebuilding process this offseason seemed inevitable.

General manager Kenny Williams did little to dispel that expectation when he traded Sergio Santos to the Blue Jays for lefty pitching prospect Nestor Molina. Though Santos is controllable at a reasonable salary through 2017, as a reliever, he was not going to be as valuable to the White Sox’s future as a potential mid-rotation starter, which Molina projects to become. The rebuilding process was still on track.

Then, last night, news broke that the White Sox had agreed to a five-year, $65 million extension with John Danks. In a vacuum, it’s a fine deal for both sides. It gives the 26-year-old Danks some financial security, while leaving open the possibility of another lucrative deal after his age-31 season. It gives the White Sox a solid number-three starter, in his prime, at a reasonable price.

The problem is that this deal throws a wrench into the rebuilding effort. Danks was one of the White Sox few truly valuable trade commodities, a player who could have brought back a couple of nice prospects from a contender in need of rotation depth.

Unless Jerry Reinsdorf is planning to open his checkbook for a free-agent binge in the near future, the ChiSox are unlikely to be in the pennant chase until at least 2014. The Tigers trump them in big-league talent; the Royals and Indians have superior farm systems. Danks does not change the former, but as a trade chip, he offered Williams an opportunity to put a dent in the latter.

By committing $65 million to Danks, the White Sox have effectively scrapped their fire sale for an attempt to contend while rebuilding. That might be fine, if they hadn’t sent the exact opposite signal with the Santos trade two weeks ago. In Keith Law’s words, they appear to be lost.

 From the Jake Peavy trade, to the Alex Rios waiver claim, to the Danks extension, Kenny Williams has shown a greater flair for bold moves than any GM in the league. Unfortunately, without a coherent plan, there’s a fine line between boldness and absurdity. The White Sox had better choose a direction soon, because they’re now on the verge of crossing it.     

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I guess I disagree with your point. 5/$65m isn't a huge financial outlay and it's not like they have any farm system right now. They do need to field 25 players for the upcoming seasons.

If he were older, I'd be against it, but if KW decides to trade him two years from now, 3 years of a 28 year old pitcher making $13m a year is still going to be a valuable commodity.
I would think a John Danks with 5 years of cost certainty is a much more tradeable asset than a John Danks with 1 year of control before heading to free agency. Given the shortage of quality pitchers available, it wouldn't surprise me at all if Danks wound up wearing a NYY or BOS jersey in 2012.
Yes, in regards to the two comments above, that was my first thought too, unless a no-trade clause was included (which isn't mentioned).

It's not like $13 million a year is cheap, but 170 innings a season (his 2011 total, perhaps more as he continues to mature) of reasonable reliability and cost control spanning a player's prime years has considerable value.
Why does it have to be New York or Boston? Why always the cliche teams? Other teams have the ability to make trades too, and better farm systems to boot.
They probably should rebuild, but who really believed the White Sox would be willing to go through the painful process? Their farm system is so bad that once they deal veterans, they start to look like the Astros pretty quick. That doesn't sound like something Reinsdorf would accept and rebuilding is not Kenny Williams' forte, either. The Santos trade might be a slight concession to the need to rebuild on the fly but it might also be trading high on a more or less fungible relief arm. They've still got Matt Thornton and Addison Reed for the back end of the bullpen, and maybe Chris Sale too if the starter experiment craps out. I'm not impressed with Molina as a return but to me that says more about the team's questionable ability to evaluate prospects than as any kind of window into their intentions for 2012.
My guess is that Williams values Danks far more than any other GM does, and he was surprised/disappointed at the potential haul a Danks trade would fetch. Whether he should be surprised by the lack of demand for a starter with one year left on his deal in a winter where the most prized pitching commodities are cost-controlled starters like Latos and Cahill is another question, but credit him for getting what he could for Santos. The farm system is so barren that even one decent pitching prospect in return significantly improves its talent base.

The White Sox are in a tough spot with so much dead money (Peavy Rios, Dunn) on the books for 2012 (and in the case of the latter two, 2013 and 2014) and so little in the pipeline in either the near or distant future. Ideally, Danks and Floyd will have strong starts and someone will throw a few prospects at Williams for them over the summer. Anything less points to a half decade of expensive mediocrity for a team that spent more for less production in 2011 than anyone this side of the Mets.
I agree. They might have been willing to rebuild in theory, but really that was only if they got what they wanted for Danks, Quentin and whoever else (Peavy, Rios, Dunn). And, like most teams, they valued their guys more than other teams did. The bottom line for me is the idea that trading Santos signals a rebuild was way overstated.
Nitpick alert. Molina is a righty.
Could work sort of like a sign and trade in the NBA. It may end up becoming more popular as the new reality of the CBA and signing limits take effect. If the compensation process for FAs is lessened it seems sign and trades will start to happen.