To be clear, I'm not necessarily saying what KW should do. I'm guessing what he'll actually do.
I'ma assume that AJ, Bonerko, Ramirez, Bacon, Rios, and TCQ will all be back in their current roles, and that Dye, Pods, and Fields will be gone. Flowers can work in at DH and C. None of the other position prospects will be ready to break camp with the big league team. Castro, Kotsay, Getz, and/or Nix might stick around. Wise can go the way of his predecessor, Timo Perez.
As for the pitching, your top 4 is set with Buehrle, Peavy, Danks, and Floyd. Hudson, Torres, and whoever can fight it out for the 5th spot. Even assuming that Dotel is gone, most of the pen probably is set, since it's not really feasible to restructure through trades at this late juncture.
That leaves KW with a boatload of money to fill the following holes: - a 2B who can leadoff (Brian Roberts?) - a second lefty in the pen - a lefthanded hitting corner OF with pop - backup CF / defensive replacement / pinch runner - backup SS / pinch runner
If JR decides to be extremely cheap, the 1st 2 spots can be filled internally with Getz/Nix and Williams. The last 2 spots also can be filled very cheaply, but they absolutely need to spend some money to fill Thome's role in the lineup, upgrading to somebody who can play the field and DH only some of the time. Pods ain't gonna hack it.
Theoretical Roster: C - Pierzynski, Flowers, Castro 1B - Konerko, Kotsay 2B - ______ (trade, Getz, Nix) SS - Ramirez, ______ (free agent) 3B - Bechham CF - Rios, ______ (free agent) RF - Quentin LF - ______ (trade, free agent) DH - rotation
SP - Buehrle, Peavy, Danks, Floyd, (Hudson, Torres, etc.) RP - Jenks, Thornton, Linebrink, Pena, Carrassco, ______ (Williams, trade, free agent)



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