15 worst free agent contracts in Chicago White Sox history

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5. Derek Holland - 2017

Derek Holland was a truly awful player for the Chicago White Sox.

The Chicago White Sox made some interesting decisions when they started the rebuild. One thing they liked to do was sign players that they thought they might be able to flip at the deadline if they were having a good year. One player who failed them in that role was Derek Holland.

Holland signed a one-year deal worth six million dollars just to have a -1.6 WAR and be cut before the season even ended. That plan did not work out as planned.

The only good thing that Holland did for the White Sox was eat innings as a starter for a team that was purposely tanking. He did manage to end up playing for four other teams all the way up until 2021 which is nice for him but he was bad on the south side.