The Chicago White Sox absolutely fleeced the Cubs when they acquired Eloy Jimenez and Dylan Cease for Jose Quintana. It was a trade that propelled the White Sox rebuild even further. They were already well on their way but adding Jimenez and Cease made things even better. It is definitely a trade that the White Sox will look back on fondly forever.
However, that trade makes the White Sox and Cubs even in bad trades with one another. On March 30th, 1992, the White Sox traded Sammy Sosa, Ken Patterson, and cash to the Cubs in exchange for George Bell. Sammy Sosa went on to be one of the better players in the history of the Chicago Cubs. He hit 545 home runs as a member of their organization so it is easy to see why trading him away was a very bad idea.
He was known as a cheater which puts an asterisk next to his career in a lot of people’s eyes but there is no doubt that he was a great player for them. If he was on the White Sox in the mid-90s, there is no doubt that they would have had a chance to win the World Series. He would have been on the same team as Frank Thomas who was one of the best power hitters of his generation. That duo would have for sure at the very least made the playoffs. This is clearly one of the worst trades that the White Sox have ever made. It makes it even worse because of the fact that it was one that benefited the Cubs.