Poll: Will The White Sox Trade Andrew Benintendi This Winter?

After winning 19 more times in 2025 than they did last season, the White Sox are showing some signs of life for the first time in a while. The beginnings of a young core centered around top prospects Colson Montgomery and Kyle Teel, both of whom impressed in their MLB debuts this year, as well as Rule 5 pick Shane Smith, appear to be forming. Controllable pieces like Miguel Vargas, Davis Martin, Sean Burke, and Wikelman Gonzalez have the look of what could be a solid supporting cast, as well.

Even with those steps forward acknowledged, however, it must be understood that the White Sox remain a long way from contention. Even with all of that improvement over a historically disastrous 2024 campaign, they still lost more than 100 games for the third consecutive season. They finished the season a whopping 28 games back of the Guardians for the division lead and a 2-2 record in March is the only thing preventing them from having lost more games than they won in every month of this year’s campaign. A 28-37 record after the All-Star break was certainly an improvement over a 32-65 first half, but even that second half record was a 92-loss pace. They allowed the 10th most runs in the majors this year while scoring the fourth fewest.

In other words, contention in 2026 remains a pipe dream on the south side of Chicago even after this season’s improvements. That surely means another year of prioritizing a farm system that has fallen into the middle of the pack on both ESPN and MLB Pipeline’s farm system rankings after the graduations of Montgomery, Teel, and Edgar Quero. Unfortunately for the White Sox, they’re running out of tradable assets. A Luis Robert Jr. trade has been speculated upon for years now, but appears to be just as much of a non-starter now as it was over the summer. Mike Tauchman’s impressive 2025 campaign could make him an attractive target for a team in need of outfield help on the cheap, but no journeyman outfielder headed into his age-35 season should be expected to bring back a big return. Players like Vargas and Lenyn Sosa won’t be free agents until after the 2029 season, a point by which the Sox are surely hoping to be back in contention.

With so few resources through which they can upgrade their farm system on the trade market, might outfielder Andrew Benintendi actually prove to be their best asset on the trade market? Benintendi is coming off his best season in a White Sox uniform, though that bar is quite low. He hit .240/.307/.431 (103 wRC+) in 116 games this year with 20 home runs, an 8.5% walk rate, and a 17.4% strikeout rate. Poor defense in left field limited Benintendi’s overall value, but he was still worth 1.0 bWAR in less than a full season of work. Heading into his age-31 season, it’s not completely impossible to imagine Benintendi building on last year’s performance and getting back into the 110 wRC+ range he sat comfortably in for his career prior to arriving in Chicago.

If Benintendi were a free agent this winter, an outfield-needy team without much money to spend surely would have interest in his services for 2025. The problem, then, is Benintendi’s contract. $31MM guaranteed over the next two seasons is hardly the most onerous contract out there, but it’s still far more money than the veteran’s production has been worth, and no team is likely to be eager to take that deal of Chicago’s hands, much less surrender significant prospect talent for it.

With that being said, the White Sox have reportedly expressed willingness as recently as this summer to pay down some of Benintendi’s salary in order to facilitate a deal. To get a meaningful return for him, the Sox would surely need to cover the vast majority of his salary for the next two years. That might not be as unreasonable as it would seem, given that RosterResource projects the club for a payroll of just $45MM next year as things stand. That figure doesn’t include the $20MM club option on Luis Robert Jr.’s services next year, but even so, the White Sox should have plenty of money to work with this winter. Essentially buying a better prospect return from a club acquiring Benintendi by paying down his salary could be the best use of those resources.

With that said, there are some obstacles to that plan. For one thing, the White Sox have shown a reluctance to sell low on their players, as shown in their handling of Robert. Another problem could be that the best fits for Benintendi might be the team’s division rivals. Small-market clubs in significant need of outfield help would be the perfect trade partners for a deal like this, but both the Royals and Guardians reside in the AL Central alongside the White Sox, and it’s unclear if the the team would be willing to pay Benintendi to play for their direct opponents for the next two seasons.

The Pirates and Rockies are two other clubs that could be at least plausible fits for a Benintendi trade, but the market would surely be much softer if Cleveland and Kansas City aren’t involved. Another option could be to simply accept little to no return for Benintendi and try to offload as much of his salary as possible, though that wouldn’t do much for the team’s long-term outlook given their existing financial flexibility.

How do MLBTR readers think the White Sox offseason will play out with regards to Benintendi? Will they be able to leverage his decent 2025 season in order to get some type of return for him this winter? Will they resort to trading him in a salary dump to get a portion of his deal off the books while they can? Or will they hold onto him and hope for improvement in 2026? Have your say in the poll below: