Welcome to the off-season. The first thing the Sox have to do is decide what direction they're headed into: "win now" or "rebuilding." I don't want to see last year's strategy of "win now and rebuild on the fly;" it didn't work at all.
Either you're playing for this year, or you're building for the future-pick a road and stick to it. Trying to play both sides produced a 90-loss season in the present and a flighty commitment to the future.
Rebuilding is a very scary word, especially in Chicago where it traditionally has been used as a synonym for "going cheap" and "perennially losing," but it doesn't necessarily have to be so negative.
The AL Central could be too difficult to climb in 2008, considering the relative strength of the Indians and Tigers and the current make up of the Sox. Adding some young players to go along with Josh Fields, and the survivors of a handful of other Sox farmhands could create a core that will be competitive for four or five years together starting in 2009.
You could trade some of the veterans (Konerko, Garland, Thome, maybe even Jenks) for several prospects and amass formidable young talent like the Florida Marlins. But unlike the Marlins, the Sox are equipped with a high payroll capacity, meaning they could actually sign these players long term when they begin to produce at the big league level and they can add a big ticket free agent to fill any holes that are left when the team is ready to seriously compete in a year or two.
Though that sounds like a plausible plan to me, the point is moot because Ken Williams has already decided he wants to "win now." And if he does, then so be it. But he better go all the way. (Bringing in Torii Hunter and calling it an off-season is not going to get the job done.)
One thing we've heard repeatedly for the past few months is that the Sox are shopping Jon Garland, who has only one year left of his contract. That brings up the biggest question: if you are going to win now, why in the world would you trade Jon Garland? Knowing full well that starting pitching is the single most important component to winning, how is the 2008 team going to improve by dealing him away?
Trading Freddy Garcia for two minor leaguers last winter was the epitome of Williams' "win now and rebuild on the fly" strategy. I'm not debating it was the better move for the long term, but it didn't benefit the '07 Sox, which, supposedly, was the top priority. The resulting feeling was that of treading water.
Unless trading Garland brings in a bona fide major leaguer that can fill one or two of the Sox holes, most importantly a major league shortstop and/or lead off hitter, I can't see any justification for trading your number three starter if you want to contend. The general consensus seems to be that Garland would not fetch anything more than a B prospects or two.
If you want to win in 2007 you hold on to Garland, period. The 5th starter quagmire has ruined several Sox seasons this decade and a starting rotation of Buehrle-Vazquez-Contreras-Danks-Floyd is watching baseball on TV in October, no question.
So the Sox first move this winter should be to extend Jon Garland for four years. If they want to compete, the starting rotation needs to include no more than one rookie.
Then we can move on to the four areas of need: a lead off hitter, an outfielder or two, a shortstop and the bullpen.