What's next for White Sox? After historic turnaround falls short, Chicago has path to sustained contention

The White Sox were one of the best stories in 2026; can they keep the good times rolling?

Oct 10, 2026 at 10:48 pm ET • 6 min read

The bad news here is that the 2026 season for the Chicago White Sox has ended. The good news is that, in the previous three installments of White Sox baseball, the season ending was the good news. After three straight 100-loss seasons, including a record 121-loss campaign in 2024, the White Sox were a win away from reaching the ALCS but fell in Game 5 to the Cleveland Guardians on Saturday after taking a 2-0 lead in the series. 

Given the circumstances, losing in the playoffs shouldn't detract from the notion that this season on Chicago's South Side was an overwhelming success. The White Sox were arguably the best story in baseball.

Some of it was being in the right place, of course, and that has to be acknowledged. The White Sox were an 84-78 team in the regular season, which was good enough to only lose out on the AL Central title by one game and earn them a wild-card spot. They then faced the 81-win Houston Astros in the Wild Card Series and beat them easily to set up the fatal date with the Guardians. They won the first two games of the ALDS, then lost three straight. Now, they head into the winter looking for ways to improve the ballclub. 

The overarching feeling here should be very, very positive. It wasn't just the number of wins or advancing in the playoffs. The White Sox found many positives in 2026 that will last them for years on the field. We'll start there and then see what areas they could stand to improve. How do they approach the offseason?

Guardians advance to ALCS with Game 5 win over White Sox: José Ramírez, Gavin Williams set date with Rays

Mike Axisa

A strong foundation of talented youth

Third baseman Miguel Vargas is only 26 years old and controlled through 2029. He's already a star after his 2026 breakout and it's possible there's another level in there, which would vault him up into MVP conversations. Chase Meidroth at second base just posted 4.5 WAR and looks like a good candidate to be an All-Star next season. He wouldn't hit free agency until 2031 even without an extension. Shortstop Colson Montgomery is also under control through 2031 and just hit 31 home runs. All-Star center fielder Tristan Peters is under team control through 2031 as well, as is catcher Kyle Teel. Outfielder Braden Montgomery could be around through 2032. 

How about the pitchers? Sean Burke had a very nice season and is under control through 2030. Stud reliever Grant Taylor is under control through 2031 and Hagen Smith only has a few months of service time. 

There's good, controllable talent all over the place. 

These guys alone don't yet make up one of the best teams in baseball, but there's plenty of room for internal improvement. Think about Montgomery hitting for better average after cutting down on strikeouts. Teel was hurt for nearly the entire season. Vargas and Meidroth could be superstars as soon as next year. The core is in place already.

Money to spend? 

Something even more exciting? The White Sox are only tied up with roughly $89 million of player salary for 2027 as things stand. 

We know this is notoriously one of the cheapest ownership groups in baseball, but their payroll in 2026 was roughly $120 million, and they weren't even really planning on contending to the extent they did. It was up around $200 million just a few years ago, so there's the possibility of a spending splurge in free agency this coming offseason, depending on the parameters of the new CBA. 

Biggest need: Rotation help

Sure, they left plenty of men on base in their two ALDS home games, but the White Sox's undoing in the playoffs stemmed from the lack of a strong stable of starting pitchers. Burke was really the only actual starter and guys like Erick Fedde and Anthony Kay were cast in creative relief roles (or very shortened starts). Smith was used as an opener and Taylor was tasked with outings that were far too long to be sustainable for a deep playoff run. 

If Smith and Taylor remain in the bullpen long term, they'll be among the best relief tandems in baseball, and it won't be difficult to fill in the bullpen around them. Taylor probably stays in the bullpen with his pitch mix unless the White Sox get really creative. Smith, though, was a starter in the minors and they likely see him as a starter long-term. 

So the rotation starts with Burke and Smith. 

Davis Martin was good for two months to start the season before falling apart. He heads to his age-30 season and is under team control. He'll be in the mix. Kay is fine to be in that group of possible starters, too, even though you'd prefer he be at the back end of the rotation or even a sixth or seventh starter. Noah Schultz didn't find success as a starter this season, but he was great in the role in Triple-A and has the pedigree as a former first-round pick and top-10 prospect.

Remember former All-Star Shane Smith? He was the Opening Day starter. He went through a disaster of a season that included injury and ended with him as a reliever for Triple-A Charlotte. Once the calendar turns to 2027, though, he'll have a shot to earn his way back. 

Luis Castillo is under contract and sure seemed washed up after the trade, but he's around. 

So there's Burke, Hagen Smith, Shane Smith, Schultz, Martin, Kay and Castillo. That's six. If there are two quality additions from outside the organization, that would mean depth and the ability to use two of these guys, at least in theory, to provide bullpen help. It would also tremendously raise the ceiling here because, let's face it, that's not exactly a stable of aces at this point. 

The pie-in-the-sky option here is Tarik Skubal. I don't think the White Sox will come even remotely close to paying what is required, but he'd be the perfect signing here. 

Soon-to-be free agent Adrián Morejón is a beast of a multi-inning reliever and could be ready to move to the rotation. The White Sox should be all over this. Sticking with the Padres, what about Michael King? Casey Mize? He was a disaster for San Diego after the trade deadline, so maybe he could be had on a short-term deal to re-establish his value as an All-Star. Freddy Peralta was fixed by the Rays, it appears, but overall, his season was bad and a similar sentiment could apply. 

If he doesn't retire, Sonny Gray could have something left in the tank. Kevin Gausman and Clay Holmes will be free agents and both seemed to enjoy their time in Chicago with the Cubs after the deadline. 

Let's say the White Sox can land something like King and Holmes in free agency. 

This rotation, teamed with a good bullpen built around Taylor and those young position players, would be nice. 

1. Michael King
2. Clay Holmes
3. Sean Burke
4. Hagen Smith
5. Noah Schultz
6. Luis Castillo

Extra depth: Davis Martin, Shane Smith, Anthony Kay

In this case, they could even leave Hagen Smith in the bullpen with Taylor.

We're just spitballing here, of course. The main thing is that the White Sox need to attack the rotation in the offseason, both internally and with talent from outside the organization. They need to capitalize on the excitement from the unlikely and incredibly fun 2026. Speaking of which ... 

A Munetaka Murakami extension? 

Murakami is 26 years old and only signed through next season. Surely the White Sox would love to keep him around for longer, as he's such an important piece in the lineup (and seemingly the clubhouse too). There's a lot of swing-and-miss, yes, but it's possible he improves there, and it isn't exactly easy to find his level of power lying around.

As noted above, the White Sox should, in theory, have a decent amount of money to spend. Why not use some of it to keep Murakami around for years?

It couldn't hurt to see what it would take to extend Vargas before the new CBA, either.