15 worst free agent contracts in Chicago White Sox history

13. Jon Jay - 2019

Jon Jay will not bring back good memories for Chicago White Sox fans.

In 2019, the Chicago White Sox were in heavy pursuit of Manny Machado. In an effort to recruit him, they brought in Jon Jay who is close to Machado off the field. It was a smart idea but it backfired on them very badly.

Jon Jay was someone that helped Machado decide on the San Diego Padres in free agency and the White Sox were stuck with him on a four-million-dollar deal. During that stretch where Jay played for them, he was incredibly bad and not worth a penny that he was being paid.

For that one bad 2019 season, he only played in 47 games because he was hurt. He didn't hit a single home run and only had nine RBIs to go with a slash line of .267/.311/.315 for an OPS of .626.

Luckily, he only had to play there the one season and the White Sox never had to see him again. It was a bad time for the franchise but they moved on quickly.