Tarik Skubal is headed for free agency, and one of the more unexpected teams linked to him is the Chicago White Sox.
The Athletic’s Jim Bowden put Chicago alongside the Los Angeles Dodgers and New York Mets as the “Best team fits” for the left-handed ace on Tuesday. That’s a notable list, especially with the Dodgers fresh off falling short in the NL Championship Series after the Milwaukee Brewers swept them to reach their first Fall Classic since 1982.
For the White Sox, the fit is striking for a different reason: they were baseball’s worst team two seasons ago, finishing 41-121, but have climbed back into relevance fast. Under manager Will Venable, Chicago went 60-102 in 2025 and then made a 24-win jump in 2026 to finish 84-78. That season was good enough to deliver an AL Wild Card berth, and the White Sox rewarded it by beating the AL West champion Houston Astros in the Wild Card round.
Their run ended in painful fashion, though. Chicago grabbed a 2-0 lead over the Cleveland Guardians in the AL Division Series, then dropped the final three games to see its season cut short.
Now GM Chris Getz and Venable are facing a different kind of offseason question: how aggressive can they get in upgrading a playoff roster? Skubal would be, without question, the biggest name they could chase.
Chicago’s rotation has some interesting young pieces in Sean Burke and Davis Martin, but it still lacks a true ace. Skubal would change that immediately.
The real hurdle is financial. The question is whether owner Jerry Reinsdorf would approve what could be the largest contract in White Sox history, and the biggest deal ever handed to a pitcher. If he does, Skubal could wind up anchoring the South Side for years.
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Recent trades have only added to the sense that this winter could bring more turnover, with the team already pulling in Braxton Ashcraft and sketching out how players like Freddy Peralta and Alec Bohm fit into the larger discussion. The intriguing part for White Sox fans is how much more movement might still be coming, because the current blueprint suggests the organization is still willing to make bigger, harder choices if it means accelerating the reset. [Read more 🡒]
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As the White Sox head toward free agency, the conversation around their roster fits is already bigger than just plugging a few holes. Starting pitching remains a need, and so does outfield depth, which is why Jim Bowden of The Athletic linked Chicago to Tarik Skubal while ranking the left-hander as the top free agent on the market and putting the Dodgers and Mets in the same bucket of possible suitors.
The tougher question is whether a club still operating under financial constraints and a fairly cautious roster-building philosophy can realistically chase that kind of impact arm. Bowdens broader point was less about a likely chase and more about the kind of decision the White Sox front office has to make if it wants to accelerate the rebuild, because the market for a star starter of this caliber is expected to test every teams appetite for spending. [Read more 🡒]
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Freddy Peralta is emerging as the more realistic high-end target for the White Sox, which says plenty about where the clubs search may actually lead. Clay Holmes, meanwhile, still lingers as a name worth watching after past trade chatter, but he looks more like a fallback than a front-line answer. Beyond that, Chicago is sorting through left-handed options such as Foster Griffin and Trevor Rogers, trying to find a path that makes sense without overreaching for the wrong kind of help. [Read more 🡒]