3 worst contracts in modern Chicago White Sox history

As a baseball general manager, some moves pan out and others don’t. It comes with the territory. The Chicago White Sox have made some boneheaded moves over the years. In 1992 they traded Sammy Sosa to the Cubs. In 1976 they traded Rich Gossage who wound up being a Hall of Famer.

In 2016, they added James Shields for some guy named Frenando Tatis Jr. In recent years, Rick Hahn has been pretty good about making moves. His ability to lock up players to team-friendly long-term contracts has paid dividends.

Because Chris Sale was signed long-term, the White Sox were able to get a pool of prospects headlined by Yoan Moncada and Micheal Kopech out of him. Jose Quintana netted the White Sox Eloy Jimenez and Dylan Cease.

However, in the White Sox modern era, there have been contracts so bad that it leaves fans scratching their heads today. These three players turned out to be useless during their time with the White Sox. While the James Shields deal turned out to be regrettable, at least Shields ate up innings for the White Sox for three years and served as a mentor in the clubhouse.

The Chicago White Sox have handed out some bad contracts in recent years.

The following is a list of the three worst contracts in modern White Sox history from the 2000s to the present.  These moves resulted in poor production, rifts in the clubhouse, and the season’s being derailed.

Because of all these factors, the team would like to have their money back. So without further ado, here are the three worst contracts in modern White Sox history: