Jesus Christ what a mess. They won't necessarily be a horrifyingly bad team, but I really can't imagine being an owner of a professional baseball team and standing idly by while my GM simultaneously creates the worst farm system in baseball, while also spending $127MM, and finishing under .500.
I probably could have told you that taking the Alex Rios deal was a bad idea, and the Jake Peavy thing was kind of iffy at the time as well, simply due to his injuries. It's not that Peavy has been terrible or anything, because he's still fairly decent when healthy, but he's only pitched 111 innings or fewer in each of the last 3 seasons, and is now past his prime seasons, even if he can stay healthy. The Adam Dunn contract seemed fine at the time, especially if the plan was to DH him, because I don't think anyone could have really predicted his fall off a cliff.
The end result of these three guys being either hurt, or terrible going forward is a nice big chunk of payroll providing not that much value. Peavy is still owed $17MM this season (plus a $22MM option or $4MM buyout), Rios is due $36.5MM between now and 2014 (plus a $1MM buyout), and Dunn is due $44MM through 2014. No one of these contracts alone will handcuff the team, but the three of them together, combined with other commitments like Paul Konerko, will take away a lot of payroll flexibility going forward.
Kenny Williams refuses to commit to a full blown rebuild, considering the payroll that this team can sustain. I think the biggest problem he has going for him right now is the fact that he hasn't gotten much use out of the salary that he's using right now, but with a lack of a farm system, the only real way to compete in the next few years (i.e. until the Rios/Dunn deals are off the books) would be to spend on free agency and have a really expensive bench. I'd have traded John Danks and Gavin Floyd already, if I were him, mostly because there's no way he's going to compete in the next 2 or 3 years. The biggest struggle Williams is going to have going forward is dealing with a division that has the peaking Tigers and the up-and-coming Royals and Indians.
Alexei Ramirez is good and plays a premium position, so he would probably get a decent haul in a trade, and you could probably turn 4 or 5 guys from that roster in to a 3-star prospect (with a bit of cash tossed on the side in some cases), so it's not utterly hopeless if they're really willing to go ahead and actually commit to a rebuild.
This farm system is the consensus worst in baseball. That's why I'd have traded Danks and Floyd. Floyd could still be moved (and Danks can be moved next year), so it's not a complete disasterfuck yet, but given the load of prospects Gio, Latos and Cahill fetched, this seems like a no-brainer, since they're not going to be winning soon anyway.
The White Sox have spent next to nothing on the draft over the last few years, and it shows. They've hardly gotten any value from their own first rounders, either due to prospects fizzling, or trading them away (they also gave away a pick when they signed Adam Dunn, who gave them -3WAR for $12MM).
I guess it's a pet peeve of mine to see a team have a $100MM payroll and finish with 80 wins or fewer without having some semblance of a positive aspect of your season.
The best-case scenario for the White Sox over the next few years is being perpetually decent. I don't see much of a fix until the Rios and Dunn contracts expire (assuming Dunn never returns to form). They really need to accumulate some assets in the form of prospects so they can have some kind of chance to compete in 2017 or so. I don't necessarily think that they completely tank this year, because they aren't absolutely awful and won't fully commit to re-tooling the organization, but they definitely aren't good enough to compete with the Tigers, and won't improve enough any time soon to compete with Indians or Royals when they get good either.
2012 Projection: 74-88, 4th in AL Central
I expect them to be worse this year than they were last year, but also expect improvements from the Royals and Indians. I wouldn't be terribly surprised if they went it to full firesale mode, in which case they could actually win something like 70 games or fewer, depending on when the sale happens, but as is, they're probably better than that right now.