White Sox spark whispers of a stunning long-term free-agent splash that no one saw coming.ht

How do you pry open the White Sox’s checkbooks? With a little external pressure, of course!

Tampa Bay Rays v Chicago White Sox
Tampa Bay Rays v Chicago White Sox | Matt Dirksen/GettyImages
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The Chicago White Sox aren’t going to be in contention for an AL Central title next year no matter what the front office decides to do over the offseason.

Three straight 100-loss campaigns have a way of sapping the optimism of a fanbase, and given the way general manager Chris Getz has spoken about the team’s plans for the winter, it’s hard to have much for hope for the immediate future of the franchise.

Getz: “Free agency is an avenue to bring in players to help in the win total. But to go beyond this upcoming season I think would be a little premature considering the state of our club right now and the development of these young players.”

— Scott Merkin (@scottmerkin) November 5, 2025

That being said, there’s a clear core of building blocks in place, and the White Sox may not be quite as far away from contending again as it may appear at first glance.

Is the presence of Colson Montgomery, Kyle Teel, and All-Star Shane Smith enough to convince the front office to make a splash in free agency? Probably not, even if they do deserve some veteran counterparts that can help the team return to relevancy.

So, it’s a good thing that a baseball-wide lockout and significant MLBPA grievances appear to be on the horizon.

White Sox could be pressured into buying free agents this offseason

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As things currently stand, the White Sox have two players under contract following the 2026 season: Luis Robert Jr. and Andrew Benintendi. That 2027 season will be the first one after the impending lockout—if it gets played at all. The economics of the sport are bound to change in some fashion or another; a salary cap and salary floor have been rumored, as has the prospect of maximum and minimum contracts á la the NBA. That year, Benintendi ($15.1 million) will be in the final season of his albatross deal, and Robert ($20 million club option) may not even be on the team by then if the club finally trades him or exercises a $2 million buyout in his contract.

Of course, there are a number of players on the roster who will be earning salaries via arbitration or pre-arb minimums, but none of that money is guaranteed. The White Sox risk being in an uncomfortable spot before and after the next round of CBA negotiations begin if they don’t get at least a little more money on the books this winter.

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This conversation isn’t new. The Athletics have been the poster boy in the spendthrift conversation for the better part of the last decade, and there’s no secret that their (relatively) luxurious offseason last year was motivated by threats of grievances from the player’s union. Notably, the Athletics spent on starting pitcher Luis Severino and signed cornerstone hitters Brent Rooker and Lawrence Butler to extensions.

None of this is to say fans should expect Chicago to pursue Kyle Tucker or a reunion with Dylan Cease. But, if another mid-level player seeking a multi-year deal like Benintendi comes along, the White Sox could pounce at the chance to add a veteran to the roster without overburdening the long-term payroll sheet.

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