3 terrible decisions that killed the Chicago White Sox rebuild

The Chicago White Sox rebuild is dead. These three decisions killed it.

Chicago White Sox v Kansas City Royals
Chicago White Sox v Kansas City Royals / Kyle Rivas/GettyImages
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The Chicago White Sox rebuild started on December 6th, 2016 when they traded Chris Sale to the Boston Red Sox in exchange for Yoan Moncada, Michael Kopech, and two others. 

The next day, they traded Adam Eaton to the Washington Nationals in exchange for Lucas Giolito, Reynaldo Lopez, and Dane Dunning. From there, they started doing a bunch of wheeling and dealing for prospects. 

Some bad years followed on the diamond as they were essentially a losing team on purpose. They had some high draft picks though which added even more high-end prospects. 

There were some good seasons in 2020 and 2021. In 2022 they were very average (81-81) but the rebuild was completely dead by 2023. There are a lot of reasons for this. 

Some bad decision-making was made by everybody involved. These are the three biggest decisions that killed the rebuild: 

The Chicago White Sox should have never hired Tony La Russa at all

One of the biggest mistakes that Jerry Reinsdorf ever made was letting Hawk Harrelson fire Tony La Russa back in the '70s. One of his other biggest mistakes was hiring him again in 2020. 

Reinsdorf went above Rick Hahn and made the hire once the team was ready to start winning. It was a terrible way to conduct business after Rick Hahn put this rebuild together. 

It seemed to be working but La Russa didn’t manage the team the way they were designed to be managed. The effects of this bad hire are still being felt. Pedro Grifol is even worse but he would never be the guy if Reinsdorf didn’t go above Hahn’s head and make that hire. 

Everything slowly but surely went downhill from that point on. Ownership should never take over Baseball Operations without talking it over with the actual baseball people. 

Yasmani Grandal’s contract is a reason why the White Sox rebuild failed

The problem wasn’t that the White Sox handed out a contract north of $70 million. It is infuriating that they are one of only three MLB teams to never hand out a $100 million contract. They are cheap. 

That contract over $70 million during the rebuild went to Yasmani Grandal. They gave a catcher the largest (at the time) contract in the history of the franchise. Grandal was an above-average pitch framer and a very good hitter during his prime but the White Sox overpaid him for what he did in the past. 

Grandal ended up being elite for exactly half of a season. In the second half of 2021, you can argue that he was their best hitter. The team ended up winning the division with a 93-69 record and was one of the best in the league. 

Towards the end, rumors were coming out about Grandal’s negative impact on the clubhouse. If that is the case, it makes the contract even worse. They gave him all of that money for a four-year-long headache. 

At the time of the Grandal signing, they still had James McCann catching for them as well. He was doing great things with the Sox and they didn’t take advantage of it. They could have ridden McCann and used that Grandal money elsewhere but they weren’t smart. 

Grandal had an up-and-down tenure with the White Sox but it was mostly down for that level of owed money. By the end of the 2023 season, he couldn’t get out of there quickly enough.

The White Sox didn’t land any of the great players during free agency

The Chicago White Sox were supposed to sign free agents to supplement the young core that they were building. Rick Hahn made it seem like they would be in on everyone available that could help them win. 

The failure here started in the off-season ahead of 2019. Bryce Harper and Manny Machado were both available. They were younger than most free agents of their status because of how early they came into the league.

Harper ended up with the Philadelphia Phillies and Machado ended up with the San Diego Padres. The White Sox claim that they tried to get both but the offers to them weren't good enough.

In hindsight, those guys never had a realistic shot at coming to the White Sox. Since then, they have missed just about everyone. Their bad ways of doing business plus being cheap are the biggest reasons why.

As long as the current ownership group is in place, the White Sox have no chance of becoming a team with sustained success year after year. All of these big problems step from Jerry Reinsdorf. It is time to sell.

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