The Chicago White Sox have been a historically mediocre franchise. They did win the World Series in 2005 which is the greatest year in franchise history but they haven't won a playoff series since.
There have been a lot of mistakes that have led to this issue for them. Now, here in 2023, they are trying to bounce back from what was a terrible season in 2022.
A large reason for this is the fact that they aren't that smart with contracts. They are one of a few teams that has never given out a 100 million dollar contract which usually goes to elite players.
Instead, the White Sox like to sign free agents that like to become disappointments. These are the 15 worst free-agent contracts in White Sox history:
15. Sandy Alomar Jr. - 2003
The Chicago White Sox brought back Sandy Alomar Jr in 2003.
The Chicago White Sox saw Sandy Alomar Jr. have some good years with Cleveland in the 90s as a division rival. They landed him in 2001 and he just wasn't the same player anymore.
He had a good start in 2002 however, so the Chicago White Sox were able to trade him to the Colorado Rockies. He had been a good player for them but it was time for him to go.
Following that season, however, the White Sox made the mistake of signing him for the 2003 season for $300K and he went back to being a below-average player again. He then played out the season with them and then was back again in 2004.
After a cup of coffee elsewhere following that, he made his way back via a trade in 2006 but he only played in 19 games for them. Sandy had a great career but the White Sox should not have brought him back in 2003 knowing he was on the decline.