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Going into free agency, the Chicago White Sox have a few holes to fill. Starting pitching and outfield depth are high on the wishlist for general manager Chris Getz. And starting pitching by far outweighs outfield depth based on what we saw in the postseason.

Could Getz take a big swing at the biggest fish out there this offseason?

Jim Bowden of The Athletic put together a list of the top-40 free agents this offseason. To absolutely nobody's surprise, Los Angeles Dodgers ace and two-time Cy Young Award winner Tarik Skubal was ranked the best free agent. The surprising part, however, is which teams he thought would be the best fit. The Los Angeles Dodgers and New York Mets are the two biggest spenders in baseball, so it would seem logical that they would pursue Skubal.

But the third team Bowden wrote as a best fit was none other than the White Sox!

Skubal is one of the best pitchers in baseball, and his reputation goes without saying. Therefore, any team in theory would want him on their ball club. Still, most teams don't have the means to acquire such talent, especially one like the White Sox. So, should Chicago even be mentioned as a possible suitor for their former division rival?

Are the White Sox Really a Destination for Tarik Skubal?

Oct 11, 2026; Milwaukee, Wisconsin, USA; Los Angeles Dodgers pitcher Tarik Skubal (29) reacts during the fifth inning against the Milwaukee Brewers in game one of the NLCS for the 2026 MLB Playoffs at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

Tarik Skubal will be one of the most sought-after free agents ever. So, why would he even consider going to a team like Chicago? Well, the White Sox are on the rise. I think everyone can agree on that! But are they a true World Series contender yet? Likely not. Even if Skubal could push them into that stratosphere, it's still unlikely that he would consider coming to Chicago because of one factor: money.

Skubal is expected to shatter the MLB records for guaranteed money and Average Annual Value by a free-agent pitcher. Bowden places his projection for the total value of the contract at $350-$500 million, depending on the length of the contract. To put this in context, the White Sox have never signed a free agent to a deal worth even $100 million. So, to say that owner Jerry Reinsdorf would be opening up his pockets would be an understatement.

While the need is certainly there, the fit is murky. Chicago's payroll is low enough that a team in their position could theoretically make a move on a free agent like Skubal. However, the White Sox don't operate outside of their means. Given the history of the franchise, it appears highly unlikely that Reinsdorf and Getz will take that big of a swing in free agency.`

While this may remind fans of 2019, when the White Sox were in the race for Bryce Harper and Manny Machado, this is a different team, a different general manager, and, more importantly, a different philosophy than the previous regime.

So, White Sox fans, if you believe that Skubal will go to Chicago, think again! The White Sox will likely build this team with affordable, solid starting pitching, rather than trying to outbid the Dodgers and Mets.

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