I'm really starting to think that KW is doing a decent job, but he is, in his mind, contradicting himself. He wants to keep key parts here that have been loyal to the club, and he wants to field a team that regardless of costs will compete well, but still is restricted by JR and the cheap regime. Therefore, sometimes he makes moves that are good money-wise(Sandy at 500-700K, bringing in 2-3 vet starters to ST to compete), but then he makes bone-headed moves like JosE6 at 5 mill and the obsurd contracts for Konerko and the severly backloaded Maggs contract.
KW has too many conflicts of interest in his head, with being still a new GM, wanting to get talent to the Southside, club loyalty, JR's cheapness, etc. I don't envy him at all.