KW with 50 cents was a lot better GM than he was when he had the dollar. The Sox have been fortunate, at least in my lifetime to have had some very creative, hardworking GMs. Frank Lane, Ed Short (at least on the front end of his tenure) Roland Hemond and KW stand out the most for me. Frank Lane got Nellie Fox, Billy Pierce, Minnie Minoso and Sherm Lollar for next to nothing. It's hard to top that. When the Sox slid 3 years in a row after winning a pennant Ed Short revitalized the team with a block buster trade that brought Pete Ward, Hoyt Wilhelm and Ron Hansen from Baltimore. Dave Nicholson too but the other 3 made up for him. Roland Hemond, like Lane breathed new life into an organization that was near comatose. KW of course did what none of the aforementioned was able to do. Of course I respect the man, but like Ed Short he made some questionable moves the last few years. It's too early to tell, but so far I think Hahn will do well and add his name to the list of noteworthy Sox GMs who did so much to keep the Sox competitive with limited resources.
Edit: Of course I should mention Larry Himes but I was thinking more of the trading aspect of the GM position, so I brain cramped.