15 worst free agent contracts in Chicago White Sox history

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.

14. Ron Blomberg - 1978

Ron Blomberg is someone that the White Sox should have avoided.

The Chicago White Sox signed Ron Blomberg in 1978 after he played for a decade in the New York Yankees organization. It came one year after he spent the year missing from baseball in 1977.

He made less than $200,000 per year with the White Sox but that was a lot in the late 70s. The White Sox paid him for four years but he only played with them on the field during the 1978 season.

During that 1978 season, he was not a very good player at all. He slashed .231/.280/.372 for an OPS of .652. He had five home runs and 22 RBIs in this stretch with the White Sox where he only played in 61 games.

If they could re-do that signing and take it back, they probably would have. He just wasn't worth the contract he got.

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.

11. Jaime Navarro - 1997

Jaime Navarro was signed by the Chicago White Sox in 1997.

Jaime Navarro was an okay pitcher for the Milwaukee Brewers in the early 1990s but he was outstanding for the Chicago Cubs in 1995 and 1996. Then, the Chicago White Sox made the mistake of bringing in a Cubs player that had a bit of success in 1997.

Navarro was nothing short of a terrible pitcher for the White Sox after signing with them. He pitched for them in 1997, 1998, and 1999 and had no success. Ahead of the 2000 season, the White Sox traded him back to the Milwaukee Brewers where he was horrible in his final MLB season.

For most of the recent past, the Chicago White Sox haven't had success with players that used to play for the Cubs. Jaime Navarro was a prime example of that.

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.

9. Adam Eaton - 2021

Adam Eaton's contract with the Chicago White Sox was horrible in 2021.

Adam Eaton started his career with the Arizona Diamondbacks before making his way to the White Sox for the 2014 season. He was outstanding there for three seasons.

Following the 2016 season, the Chicago White Sox made an amazing trade involving Eaton. They sent him to the Washington Nationals in exchange for Lucas Giolito, Dane Dunning, and Reynaldo Lopez. Of course, Dunning became Lance Lynn in another trade with the Texas Rangers.

The bad part came ahead of the 2021 season as the White Sox brought Eaton back for seven million dollars. He was terrible and cut before the season was even half over. It was never a good idea to bring him back late in his career and they realized it quickly.

8. Mike Clevinger - 2022

Mike Clevinger is already a terrible free agent signing for the White Sox.

It didn't take long for Mike Clevinger to become one of the worst signings in the history of the Chicago White Sox. After having a tough 2022 season (coming off Tommy John surgery), he was already a question mark off the field.

Then, a few weeks before spring training started, we found out that Clevinger is being investigated for off-the-field issues. The Chicago White Sox should not be doing business with people like this but they always find a way to make the wrong move.

Before he even makes a pitch for them, they should be finding a way to get rid of him. He does not deserve to be paid the eight million dollars or even be considered for the team.

7. Joe Kelly - 2022

Bringing in Joe Kelly seemed smart for the White Sox but it wasn't.

Joe Kelly was a terrible decision by the Chicago White Sox. However, that opinion comes to us all in hindsight. It was clearly something that everyone liked when it was first announced but now we aren't so sure about it.

Kelly was either injured or hurt during the 2022 season and nobody has much faith that things are going to be better in 2023 for him. He has been a great player and a champion in his career but his White Sox tenure is a disaster.

For seven million dollars in 2022 and nine million in 2023 for a negative WAR reliever, this is a horrid free-agent signing.

6. Welington Castillo - 2018

Welington Castillo was a terrible signing for the Chicago White Sox.

The Chicago White Sox have made some bad signings. There were some that took it to a new level while they were rebuilding which is fun to look back on at this point. Welington Castillo was signed to a two-year deal worth 15 million dollars and he had a -1.3 WAR during that time.

He was an awful player for them and they were very lucky that James McCann eventually came along. Yasmani Grandal, although he is also on this list as well (for different reasons), looks like a Hall of Fame catcher compared to Castillo.

Castillo was the first-ever Chicago White Sox player to receive an in-season suspension for PEDs. Again, just a disaster of a signing in every way.

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.

4. Dallas Keuchel - 2020

Things did not go well for the Chicago White Sox and Dallas Keuchel.

Dallas Keuchel was not a good player for the Chicago White Sox outside of the one short 2020 season in which he was a Cy Young-caliber starter.

Things got so bad for him in 2022 that he ended up being cut. Following that, news of him being a back locker room guy got out there and he ended up with two other organizations.

It seemed like a great signing for one 60-game season but it turned around quickly. Looking back on the deal, it was a terrible decision by Rick Hahn and his staff. The day they cut him was celebrated hard by White Sox fans as the team couldn't win when he made starts.

3. Adam Dunn - 2011

Adam Dunn is someone that couldn't lead the White Sox to the playoffs.

Adam Dunn was brought in to be a great power hitter for the Chicago White Sox. He was during the 2012 season and he even made the All-Star Game but he will always be remembered as a major disappointment.

The White Sox made a big deal about bringing him in but it did not work out for them at all. Outside of his 25 games that he played with the Oakland A's to end his career, the White Sox were the team he was the worst with.

He had an OPS near or above .900 with every other team he played for before that. It was almost like putting on the White Sox jersey made him become a below-average player which made him an incredibly disappointing free-agent signing.

2. Nick Swisher - 2008

Nick Swisher was no-good for the Chicago White Sox during his tenure.

Nick Swisher comes up on the Chicago White Sox postgame from time to time because Ozzie Guillen will be talking badly about him. He was someone that made the Chicago White Sox worse because of the way he treated people.

He had okay production for the White Sox during his one year but this was nothing short of a player who caused more negative for the team than positive. They went to the playoffs in 2008 when he was there but they didn't win a round.

From the White Sox, Swisher went to the New York Yankees and won the World Series with them a year later which was tough for White Sox fans to see but it was nice to see him out the door anyway.

1. Adam LaRoche - 2015

White Sox fans won't soon forget Adam LaRoche's tenure in Chicago.

Adam LaRoche actually had a really nice Major League career. He was a Gold Glove-caliber first baseman in his career in addition to making an impact with his bat pretty much everywhere he went.

The only team he was terrible with was the Chicago White Sox. He signed with them and made 12 million dollars to have a 0.8 WAR. He was literally a terrible player during the 2015 season.

Following that, he cause a locker room stir that caused a debate league-wide. Even the national sports media scene got in on this debate. He ended up retiring early, less than a month before the 2016 season started because some White Sox players didn't love that he had his kid there every day.

Some of these contracts are worth laughing at and some of them are enough to make any White Sox fan incredibly mad. There will be more over time but we can only hope they are fewer and farther between.