After improving by 19 wins from their disastrous 2024 season, the White Sox finally showed some signs of progress in 2025. A young core is beginning to take shape around top prospects Colson Montgomery and Kyle Teel—both of whom impressed in their MLB debuts—as well as Rule 5 pick Shane Smith.
Other controllable players such as Miguel Vargas, Davis Martin, Sean Burke, and Wikelman Gonzalez could form a respectable supporting group moving forward.
Still, Chicago remains far from contention. Even with those strides, the team lost over 100 games for the third year in a row, finishing 28 games behind the Guardians. Their 2–2 start in March was the only thing keeping them from having a losing record in every month of the season.
A post-All-Star break improvement to 28–37 was better than their 32–65 first half, but that still equates to a 92-loss pace. They finished with the 10th most runs allowed and the fourth fewest scored in the majors.
In short, the White Sox are still in rebuild mode heading into 2026. With their farm system now ranked in the middle of the pack by ESPN and MLB Pipeline—largely due to the graduations of Montgomery, Teel, and Edgar Quero—they’ll likely spend another offseason focused on development rather than contention.
Unfortunately, they’re short on tradeable assets. A potential Luis Robert Jr. deal continues to be unlikely, and while Mike Tauchman’s strong 2025 could draw some interest, his age (35 next season) limits his value. Players like Vargas and Lenyn Sosa are under team control through 2029, which means Chicago will likely hold onto them.
That leaves Andrew Benintendi as perhaps their most realistic trade chip. The veteran outfielder is coming off his best year in a White Sox uniform, hitting .240/.307/.431 (103 wRC+) with 20 homers and solid plate discipline in 116 games. His defense dragged down his value, but he still managed 1.0 WAR in limited action. At 31, it’s possible he could rebound to the 110 wRC+ range that defined his pre-Chicago years.
If Benintendi were a free agent, an outfield-needy team with a tight budget would likely be interested. However, his contract—$31 million guaranteed over the next two seasons—makes a trade difficult. While not immovable, it’s more than his recent production has warranted, and few teams would give up real prospect capital to take it on.
The White Sox have shown a willingness to pay down Benintendi’s salary to facilitate a trade, something they may need to do again this winter. With a projected 2026 payroll around $45 million (not including Luis Robert Jr.’s $20 million option), Chicago can afford to “buy” a better prospect return by covering most of his remaining contract.
That plan does have hurdles. The front office has been hesitant to sell low on players—see Robert’s case—and some of Benintendi’s best potential fits might be within the division. Both the Royals and Guardians could use outfield help, but the Sox may not want to subsidize a rival’s roster. Other possibilities include the Pirates and Rockies, though the market would be softer without Cleveland or Kansas City’s involvement.
Alternatively, the team could simply dump salary and move Benintendi for little return, but that wouldn’t help much given their current financial flexibility.
So what’s next for Chicago? Will they turn Benintendi’s solid 2025 into a modest prospect haul, offload his deal in a salary dump, or keep him and hope for further improvement in 2026?
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