The Chicago White Sox are in the middle of another difficult season. Chicago's 48-86 record currently has them sitting in last place in the American League Central standings. The White Sox are clearly rebuilding — and they should consider trading a specific player during the upcoming offseason.
Outfielder Luis Robert Jr. was mentioned in trade rumors before the 2025 trade deadline. Robert was not traded, however. He is currently dealing with an injury and it remains to be seen if the White Sox will pick up his club option for the 2026 campaign.
Robert is not the player we will be discussing today, though. Rather, the White Sox must consider trading outfielder Andrew Benintendi this offseason.
White Sox should trade Andrew Benintendi?
Benintendi, 31, has not been mentioned in trade rumors all that consistently despite the White Sox's struggles. The left-handed hitting outfielder joined the Sox in 2023 and has endured ups and downs with the ball club. His 2025 season has been especially disappointing. Benintendi has still produced enough to potentially catch teams' interest in trade talks, though.
As of this story's writing, Benintendi has recorded a .235/.298/.407 slash line across 100 games played. After hitting 20 home runs a season ago, however, Benintendi has crushed 15 long balls up to this point in the '25 campaign. His career-high for home runs in a single season is 20, a number Benintendi could possibly surpass this year — although that is unlikely with September already right around the corner.
It is fair to say that Benintendi has been disappointing, but it is also fair to assume that teams in need of left-handed hitting corner outfielders could have interest in the veteran. A former All-Star and Gold Glove winner, Benintendi features the ability to potentially make a big impact for a contending ball club.
He is under contract for two more seasons following 2025. Benintendi is set to make over $17 million in 2026 and $15 million in 2027. While some may argue that his production is not matching his contract, others could argue that his contract will increase certain teams' level of interest.
As opposed to a one-year rental, teams would receive two guaranteed seasons of Andrew Benintendi if they acquired him during the upcoming offseason. Perhaps a change of scenery would help Benintendi perform at a more consistent level.
What could White Sox receive in Benintendi trade?
The reason for trading Benintendi this offseason as opposed to waiting until next summer or next offseason is largely due to the two years remaining on his contract. The White Sox are not close to competing, so there is no reason to keep a struggling veteran outfielder on the roster. Maximizing the trade value he has remaining would be the best move Chicago can make.
Sure, there is a chance that Benintendi plays well to begin 2026 and boosts his trade value. However, there is also a chance that Benintendi performs at the same level or worse while his trade value continues to decrease since contenders wouldn't receive two full years of the outfielder.
If the White Sox trade Benintendi this offseason, they could potentially receive multiple intriguing prospects. Chicago may be able to acquire one high-value prospect or two-three prospects with respectable potential. Either way, trading Andrew Benintendi this offseason would go a long way towards positively impacting the White Sox's future amid their rebuild.
