3 biggest questions the White Sox are facing as the 2026 offseason begins

After a historic 2026 season that saw the White Sox become the first team in MLB history to reach the postseason following three-straight 100-loss seasons, it’s hard to not be happy with the team’s progress. Yes, the ending was disappointing, especially considering how close the White Sox came to an ALCS berth, but the season as a whole was one of great progress. The White Sox have been here before and watched it all go downhill after a promising season, so the job for GM Chris Getz and manager Will Venable is even more difficult this offseason. The White Sox face questions about if and when the 2027 season will begin with a lockout looming, but a few other questions about how to move forward after a big step this year. Here are the three biggest questions facing Chicago as the offseason begins. 

How aggressive should they be in adding to the roster? 

The 2025-2026 offseason was a busy one for Chris Getz and the White Sox, but most of the moves the team made were marginal upgrades. A year later, they find themselves in an interesting position. Sean Newcomb and Randal Grichuk are the only big-time contributors headed to free agency, so the overwhelming majority of the roster will be back in 2027, but it’s clear they have some improvements they can make. The White Sox lineup led the American League in runs scored but faltered in the ALDS, and they relied heavily on platoons during the season. With questions about a few positions, could they be aggressive in adding to the lineup or do they continue to give primary at bats to their young players and hope for a step forward? 

Then, of course, there’s the starting rotation, which seems like a mystery behind Sean Burke. The team could benefit from adding multiple impact starting pitchers, but that wouldn’t leave clear opportunities for players like Hagen Smith, Noah Schultz, and David Sandlin to fully transition into a starting role. It’s going to be a difficult balance for Chris Getz to find. Entering 2026, the expectation was development and the most important factor was giving young players opportunity. Now that the team has reached the Postseason, the expectation has changed. Anything less than equal performance in 2027 would be a failure, so Getz and Venable will have the difficult task of giving young players opportunity while also maintaining the team’s success. 

When and where will their top prospects play? 

As many big league debuts as the White Sox have seen over the past two years, they’re far from finished. In fact, two of the most exciting prospects to join the organization in a long time are on track to debut in 2027. Caleb Bonemer and Roch Cholowky are both infielders by trade, but the White Sox infield seems to be in shape for years to come. That raises the question of where they can make room for some of their top talents. Caleb Bonemer ended the season playing outfield with Double-A Birmingham and has done so in the Arizona Fall League as well. He’s athletic enough to hold his own at the position, so it seems  like that could be the plan for the team’s second-ranked prospect. That brings us to Cholowsky, who could also be on track for his big league debut in 2027 and also plays the infield. Could a position change be in store for him as well? Do the White Sox trade an infielder to make room on the roster? Perhaps Murakami becomes a primary DH, with Miguel Vargas moving to first and opening up third base. This is a plan that will surely be at the forefront of the minds of the White Sox front office this offseason. 

Which pitchers are starters and which are relievers? 

It’s difficult to determine what kind of needs the White Sox will have in the starting rotation without knowing who they already have. Sean Burke is an easy one, and Davis Martin was a reliable contributor for a good portion of the season, but behind that, the White Sox pitching situation is murky. Top starting prospects Hagen Smith, Noah Schultz, and Tanner McDougal all moved to the bullpen at the end of the season. With each having varying degrees of success, the team will need to decide which, if any, they’d like to turn back into starters next year. That doesn’t even factor in Anthony Kay, Luis Castillo, David Sandlin, or Shane Smith, who will be in the mix next year as well. There’s been discourse about whether the White Sox should stretch out Grant Taylor and make him a starter as well. There’s no question that the team needs pitching reinforcements, but before they determine how many, they need to decide what they have heading into the spring.

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