2027 Chicago White Sox: Examining the starting rotation

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2027 Chicago White Sox: Examining the starting rotation

Oct 10, 2026; Cleveland, Ohio, USA; Chicago White Sox pitcher Sean Burke (59) delivers a pitch during the second inning against the Cleveland Guardians in game five of the ALDS for the 2026 MLB Playoffs at Progressive Field. Mandatory Credit: David Dermer-Imagn Images | IMAGN IMAGES via Reuters Connect

Tim Healey · Da Windy City

Mon, Oct 19, 2026 ·

9 min read

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The 2027 Chicago White Sox will need pitching. Anyone who watched the 2026 Chicago White Sox knows that.

White Sox manager Will Venable was often using openers and bullpen games in the season's second half and during the playoffs less because that was his preferred style and more because he simply needed to. Injury and poor performance forced him to.

Two examples of that are Davis Martin and Luis Castillo. Martin was dominant in the first half but struggled after the All-Star Game and eventually went on the IL with a blister. That blister may have also served as cover for him to get some rest and reset -- though we've now learned he had a leg injury of some kind near the seasons end.

Castillo was the top trade deadline acquisition and had one very good start but otherwise struggled. He's still under contract, so the Sox will have to either get him better or get him gone in a trade.

As of now, if there's no change, the Sox's rotation would be Sean Burke, Martin, Anthony Kay, and Castillo in some order, plus a fifth man. That wouldn't be bad if the Sox had first-half Martin and the Castillo they expected to get working along with the reliable Burke, especially if Kay stopped struggling in the middle innings and started going deeper in games.

But as it is, unless Kay and Castillo improve a lot and unless Martin is better, that rotation won't cut it.

The Sox have said that at least one of these relievers -- Hagen Smith, Noah Schultz, and Grant Taylor could be stretched out to be a starter. Even if that works, I suspect the Sox will need one or two starters from outside the organization, acquired via trade or free agency.

I'll examine the internal rotation candidates below, wrapping up with a quick pass through the free-agent class, ending with my guess at what the rotation would be and what I hope it will be. Baseball Reference provides the stats and Spotrac the contract info.

A look at White Sox pitching, now and next year

Let's start with the current rotation, such as it is.

Sean Burke

Burke was the most reliable Sox starter, and he was great in Game 5 of the ALDS -- he was just unlucky when White Sox serial killer Jose Ramirez hit a pitch in the dirt out of the stadium for the game's only runs. He'll be the staff ace next year -- not much else needs to be said.

Davis Martin

I don't think Davis Martin will be the monster he was in the first half of the season -- nor do I expect him to be as bad as he was in the second half. If he's somewhere in between, he can be a solid number two or three starter for the White Sox.

Anthony Kay

The lefty has two problems -- he plunks too many batters and he struggles to go past the fourth inning. Whether's that's a third time through the order issue or a stamina issue or both, it's a problem. If the Sox could get five solid out of Kay on a regular basis, he could be a future rotation piece.

Other Candidates

The Sox have indicated that at least one of Noah Schultz, Grant Taylor, or Hagen Smith will be made a starter next year. Luis Castillo is still here. We'll also take a look at free agents at the end.

Noah Schultz

Schultz probably came up too early. He initially struggled to throw strikes, then he got better at that -- but his strikes were getting batted around. He did seem better in mostly low-leverage situations at year's end. I think he will be a starter someday, but I also wonder if he needs more minor-league seasoning.

Hagen Smith

Smith did generally well as an opener and can be tough to hit. He's my choice to stretch out to start.

Grant Taylor

If the Sox revert back to having a more traditional approach to a pitching staff, I'd make Taylor the closer. Yes, he had a terrible inning when the Sox had chance to clinch against Cleveland, but he was heroic earlier in the postseason (he also had some general struggles against the Guardians). I think he has closer stuff and the closer mentality.

Luis Castillo

This is the big one. Castillo has an albatross of a contract and wasn't very good after being acquired at the trade deadline. If his issues can be fixed, the veteran could be a huge part of next year's rotation. But if they can't -- can the Sox flip him and his deal for reinforcements?

Erick Fedde

The pending free agent did yeoman's work and if he re-signs, he could be a fifth starter or a long-reliever bulk guy. I think the Sox should re-up and use him in one of those two roles.

Prospects

Drew Thorpe, David Sandlin, Shane Smith, and Jonathan Cannon are all starters to watch at the minor-league level. Sandlin had some decent outings late in 2026, and Thorpe is likely to be up with the big club at some point in 2027. Smith struggled in three big-league starts in Chicago, and Cannon spent most of his year at Charlotte, where he was 5-7 with a 4.78 ERA and 121 strikeouts in 122 1/3 innings.

Sandlin or Thorpe could be a fourth or fifth starter. Smith or Cannon could be, too, but both need work to return to the big club as regulars.

Free Agents

Aug 25, 2026; Phoenix, Arizona, USA; Chicago Cubs pitcher Clay Holmes against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images | IMAGN IMAGES via Reuters Connect

The list of free-agent starting pitchers is too long to list here, and some of the highest-WAR guys are probably too close to the end of their career, but some names stick out. The Sox are probably not going to spend for someone like Tarik Skubal or Freddy Peralta. Casey Mize is only 30. Kris Bubic is out there. Steal Foster Griffin from the Guardians? Go after Clay Holmes, who may have been a trade target earlier this year?

Could Lucas Giolito return with hopes of finding his magic from a few years back? I doubt it. But Walker Buehler is intriguing.

Trades might be the answer to the questions at starter.

The rotation as I see it should be some combination of Burke, Martin, Kay, and two external candidates -- or one external and Hagen Smith. Re-sign Fedde and have him as the long guy out of the pen. If Castillo is in the rotation, he'd better be the guy the Sox wanted, not the guy the Sox got.

Sandlin, Thorpe, Smith, and Schultz might all be rotation guys someday, but other than Smith, I think that group still needs some seasoning, though Thorpe was knocking on the door in 2026. He could prove me wrong.

Two solid veterans, Burke, Martin, and Kay as the number five. That could be enough to get it done, depending on who the veterans are.

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This article was originally published on www.dawindycity.com as 2027 Chicago White Sox: Examining the starting rotation .

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