First, Jake Peavy balked at the idea of heading to the South Side of Chicago. Now, Roy Oswalt reportedly said thanks, but no thanks to the White Sox. With two veteran pitchers saying no to the White Sox, it makes you wonder. Why don't players want to play for the White Sox?
On the surface, the White Sox seem like an excellent team to play for. They are less than five years removed from a World Series championship. They have an owner who has seven championships between the two teams he owns. Their stadium is fairly new, and in a top-three media market. The White Sox have a fervent fanbase, and even cool-looking uniforms. Why wouldn't a top pitcher want to come to Chicago?
First, pitchers know that U.S. Cellular Field isn't the friendliest place to throw a ball, but that isn't nearly as important as the other x-factor, Ozzie Guillen. His lack of predictability can make him a difficult manager. The bullpen, or lack thereof, also hurts the White Sox abilities to draw in the best players. There isn't much sense in pitching your heart out if your bullpen loses the game anyway.
This does not mean that the White Sox won't be able to sign big name free agents. It just means that Chicago needs to work a bit harder to bring in those players.