The one thing you always have to consider is how many World Series rings do the 1990's Indians and 2000's Twins have? None. While I'm not for completely mortgaging our future, if the right guy(s) are out there, you have to go for it -- even at the expense of good prospects.
I'd love to put together a team that wins consistently like the Braves of the last decade and a half, but I also want to see the White Sox win the Series more than anything. Kenny has been better at signing quality free agents than in making impact trades or developing young talent, so if the right guy(s) is out there, you gotta go for it.
I do agree, though, the Sox have seemingly remade their organization into one that plays better fundamentals, has locked up some of our key players and is moving forward with some good looking young talent on the horizon.