White Sox Offseason: What Happens With Luis Castillo?

After a disastrous finish to 2026, the Chicago White Sox face a difficult decision about Luis Castillo's role and future with the team.

Acquiring right-handed pitcher Luis Castillo in a trade was a high-upside swing for the Chicago White Sox at the 2026 trade deadline. One that had some merit.

I won't shy away from the fact that I endorsed the trade for Castillo at the time. For a White Sox team looking for starting pitching help in 2026 and beyond, acquiring a three-time All-Star who had been a frontline arm as recently as 2025, with multiple years of control remaining, felt like a risk worth taking.

But it backfired in a major way for Chicago. Aside from one fluke start against the Cincinnati Reds, Castillo was a nightmare every time he took the mound in a White Sox uniform. Over nine appearances, he pitched 31 innings with an 8.42 ERA, allowing 44 hits, 29 earned runs, and nine home runs.

It raised his overall season ERA to 5.85. Now, Castillo will turn 34 years old over the winter and is owed $22.75 million by the White Sox in 2027.

That's a nightmare, especially if that number impacts Chicago's financial flexibility and willingness to spend on other free agents who could actually help the team.

As a result, Castillo seems to have been placed out of sight and out of mind by White Sox fans. He hasn't been part of the conversation regarding 2027. But he should be and has to be. That $22.75 million figure isn't going anywhere. And even if Castillo won't be part of the roster, it's still important that we ask the question: What will happen with Luis Castillo this winter?

Jesse Rogers of ESPN labeled it as the biggest offseason question facing the White Sox.

That probably overstates its significance, though it is an interesting conversation when breaking down Chicago's roster needs.

We know the starting rotation is a point of emphasis for the White Sox front office. But just as the team needs to evaluate young pitchers in the organization, like Noah Schultz, David Sandlin, and Drew Thorpe, and determine what's next for Hagen Smith and Grant Taylor, they'll also need to answer questions about whether Castillo can contribute to the starting rotation in 2027.

GM Chris Getz said during his end-of-year press conference that he believed a right shoulder impingement, the injury that landed Castillo on the IL in September, ultimately hindered his performance down the stretch.

Could a bounce-back from that injury restore Chicago's faith in Castillo as a productive starting pitcher?

I'd find it shocking at this point if Luis Castillo wasn't with the White Sox when they report to Camelback Ranch for Spring Training in 2027. That contract isn't tradable. It's also not one the White Sox are going to move on from without first giving him an opportunity to rediscover himself.

I think he ultimately ends up in the bullpen. The White Sox seem self-aware enough to know that the starting rotation needs an upgrade. I don't think they're delusional enough to believe Castillo can be that upgrade.

I think Chicago gives him a shot in a relief role, where he'll be an (extremely) overpaid multi-inning arm. But if his struggles persist early in the season, he could promptly be designated for assignment.

Looking ahead to 2027, I'm saving a roster spot for Luis Castillo, but not a place in the starting rotation. I think it's important that the White Sox do the same.

Betting on Castillo cost them dearly in 2026, and I don't think Chris Getz makes that same mistake moving forward.