The Los Angeles Dodgers' quest to become three-peat World Series champions came up short in the NL Championship Series (NLCS). The Milwaukee Brewers swept the Dodgers on their way to their first Fall Classic appearance since 1982. With the offseason swiftly approaching, the free agent market is already abuzz. Ace starter Tarik Skubal, fresh off his effort to help the Dodgers get back to the World Series, will hit the open market. According to The Athletic's Jim Bowden, Skubal would certainly fit back in with the Dodgers. However, Bowden also mentioned another surprising team fit: the Chicago White Sox.

“Best team fits: New York Mets, Los Angeles Dodgers, Chicago White Sox,” wrote Bowden on Tuesday.

The White Sox were baseball's worst team two seasons ago, going 41-121. However, the team has turned it around. Under manager Will Venable, Chicago improved to 60-102 in 2025, followed by a 24-win jump in 2026. After finishing 84-78 and clinching an AL Wild Card spot, the White Sox defeated the AL West champion Houston Astros in the Wild Card round. However, after taking a 2-0 series lead against the Cleveland Guardians in the AL Division Series (ALDS), Chicago lost the final three games to end their season early.

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Now, GM Chris Getz and Venable will look to improve a playoff roster. Skubal would be, by far, the best free agent pickup they could make. The White Sox rotation does have some promising young arms, such as Sean Burke and Davis Martin, yet they could use a true ace. Skubal would fill that role and more. The question is this: will Chicago owner Jerry Reinsdorf sign off on what could be the biggest contract in franchise history, but the biggest deal ever given to a pitcher? If so, then the lefty ace could join the team that calls Chicago's South Side home for years to come.