No. 7: Bobby Bonilla to the Pittsburgh Pirates for José De León - July 1986
Bonilla is now best known for the ridiculous contract that he signed with the New York Mets. However, many have forgotten that his storied career began all the way back in 1986 with the White Sox.
After being selected in the Rule 5 Draft from the Pirates by the Sox, Pittsburgh came back around and traded for the eventual All-Star. Of course, his career began to really take off once he left Chicago.
After returning to Pittsburgh, Bonilla made four straight All-Star Games and emerged as one of the game's top offensive players. He went on to have a highly successful 16-year career, performing well at every non-White Sox stop along the way.
De León never amounted to much with the White Sox, making this trade a loss through and through. He looked sharp in 13 starts after the trade but his first full season with the club saw him post an ERA north of 4.00 with nearly 100 walks.
He was flipped to the Cardinals in 1988 and did ultimately return to the White Sox in 1995, but his lack of noteworthy performance makes this deal a tough one since Bonilla experienced so much success after leaving Chicago.