10. Yasmani Grandal - 2019
Yasmani Grandal wasn't all that good of a signing for the White Sox.
Yasmani Grandal was brought in after the 2019 season ended. For a hot minute there, it looked like Grandal's 74 million dollar contract was the beginning of a new White Sox era in which they were going to act like a big market/serious franchise.
At the time of the signing, it was the largest contract ever handed out by the Chicago White Sox. Since then, only Andrew Benintendi has passed him. That thought that they would be big spenders going forward has all but failed.
Grandal was outstanding in 2021 but that was really his only great year with the team. He has been a massive disappointment on a team that is wildly underachieving.