White Sox Offseason: What to Do With Andrew Benintendi

2027 will be the final year of a five-year, $75 million contract between the Chicago White Sox and outfielder Andrew Benintendi. To date, it remains the largest contract in franchise history, but it's not one that has aged particularly well, even with Benintendi's improved performance over the last few seasons.

In 2026, Benintendi hit 15 home runs with a .715 OPS, though he did serve as one half of a valuable platoon tandem as the primary designated hitter against right-handed pitching, complementing Randal Grichuk nicely.

All 15 of his home runs came against right-handed pitching, and Benintendi posted a .741 OPS in those platoon opportunities. But when you factor in his lack of defensive value and the fact that Benintendi is now 32 years old, it's difficult to argue that his production will be worth the $15.1 million the White Sox owe him in 2027.

Naturally, that raises questions about whether Chicago should keep him in the fold for the final year of his contract.

So what should the White Sox do with Andrew Benintendi? They have a few options, and each comes with its own set of complications.

The easiest option would be to leave things as they are. After all, there's only one year remaining on Benintendi's contract, and there's an argument to be made that he brings value to the White Sox beyond what the statistics reflect, particularly through his veteran leadership.

Especially if Randal Grichuk departs in free agency, it may be important for the White Sox to retain Benintendi's veteran presence in a young clubhouse.

Another option would be for the White Sox to move on from Benintendi entirely and simply absorb the remaining salary he's owed. Essentially, Chicago could consider the money a sunk cost and release Benintendi to clear a roster spot, allowing the team to get younger and more athletic.

We know GM Chris Getz wants to improve the outfield and turn it into a strength of the team next season. But with Benintendi on the roster, along with young players like Sam Antonacci, Tristan Peters and Braden Montgomery, Chicago would have very limited flexibility to make significant upgrades, even if Benintendi were relegated exclusively to the designated hitter role.

A contending team needs more production from its designated hitter than what Benintendi can provide at this stage of his career. But do I see the White Sox eating $15.1 million in salary just to move on from Benintendi? I do not. Not with their track record.

So what's the happy medium? Perhaps the White Sox should explore trading Andrew Benintendi.

There should be a number of teams looking to add veteran leadership and a competent platoon bat, particularly those with lower expectations and more roster flexibility. Those teams will likely be looking to make additions at a discounted price compared to what they'd find on the free agent market.

If the White Sox can trade Andrew Benintendi and convince another team to absorb even a small portion of his remaining contract, it would make the financial loss easier to stomach and could potentially bring back a lottery-ticket prospect in return.

Ultimately, this wouldn't be a trade about getting fair value for Benintendi. It would be about freeing up roster space and creating opportunities to upgrade the lineup.

Perhaps the White Sox won't find a taker and will enter the 2027 season with Benintendi still on the roster. But how Chicago handles this situation could have a significant impact on the team's approach to free agency this offseason.

And if I had things my way, I'd like to see the White Sox move on from Benintendi and aggressively pursue upgrades in the outfield and at designated hitter this winter.