White Sox’s $75 million disaster called out in worst way imaginable

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White Sox’s $75 million disaster called out in worst way imaginable

Originally posted on ChiCitySports | By Matthew Schmidt | Last updated May 27, 2026 12:45 PM ET

The Chicago White Sox have been one of baseball’s biggest surprises thus far in 2026, as they are sitting at 27-27 and firmly in contention in the AL Central race when just about everyone expected them to finish in the cellar again.

I’m not even sure the White Sox themselves anticipated they would be performing like this two months into the season. Nevertheless, here we are, and while Chicago has slid a bit recently, going 5-6 over its last 11 games, it looks like the White Sox are here to stay.

Of course, Chicago may still need to make some roster adjustments in order to ensure its best possible chance of a playoff push.

The White Sox have between now and the MLB trade deadline to make some moves, but whether or not they choose to buy or sell (or a little bit of both) remains to be seen. One thing is for sure: they could certainly use some help with their lineup depth, and one of the biggest culprits of Chicago’s shaky offense is Andrew Benintendi.

In fact, Bleacher Report’s Zachary D. Rymer dubbed Benintendi as the club’s least valuable player this year.

Andrew Benintendi is hurting the Chicago White Sox

May 23, 2026; San Francisco, California, USA; Chicago White Sox designated hitter Andrew Benintendi (23) during the fourth inning against the San Francisco Giants at Oracle Park. Mandatory Credit: Darren Yamashita-Imagn Images

The White Sox signed Benintendi to a five-year, $75 million contract back in December 2022. At the time, it looked like a solid deal. After all, the outfielder was coming off of an All-Star campaign the season prior in which he slashed .304/.373/.399 over 521 plate appearances between the Kansas City Royals and New York Yankees.

Needless to say, Benintendi has not lived up to expectations in Chicago, and Rymer has taken him to task for it.

“Good defense used to be one of the things the White Sox were supposed to get out of Benintendi’s $75 million deal. Now he’s a DH, and one with only a 78 OPS+ to show for 170 plate appearances. And nobody likes a DH who can’t hit,” Rymer wrote.

Benintendi is slashing .228/.273/.361 with three home runs and 23 RBI across 173 trips to the dish in 2026. He began transitioning to a designated hitter role last season, and now, he is essentially a full-time DH … one who owns just a .693 OPS over the course of his first three-plus seasons in the Windy City.

Perhaps the White Sox should consider sliding Everson Pereira into the DH slot once he returns from injury, but the problem is that Benintendi is making $17.1 million this year and is set to collect another $15.1 million in 2027.

Chicago would obviously love to jettison Benintendi, but good luck trading that contract.

This article first appeared on ChiCitySports and was syndicated with permission.

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