Andrew Benintendi’s contract remains a detriment to the White Sox in more ways than just on-field performance.

The Chicago White Sox signed Benintendi to a five-year, $75 million deal before the 2023 season — a last-ditch effort to salvage their fading core and squeeze out one final playoff push. The club had gone from AL Central champions in 2021 to an even 81–81 in 2022, and that team trotted out AJ Pollock and Gavin Sheets as regular outfielders. They needed proven, long-term outfield help with Eloy Jiménez clearly trending toward a full-time DH role.

That’s where Benintendi came in.

A Gold Glove left fielder coming off a season with a .304 batting average and an All-Star nod, his signing was a surprise to fans — but a welcome one. For once, the front office was actually spending money to improve the lineup after leaning on internal patchwork in previous years.

But it hasn’t worked out. Benintendi has never come close to matching the value of his contract, and the team collapsed around him.

In 2023, he hit .262 with 34 doubles but only five home runs and a .682 OPS. His power ticked up in 2024 — he tied his career high with 20 homers — but a .289 OBP dragged his OPS to .685. Still below league average.

His 2025 season was his best in Chicago. He hit another 20 home runs and posted a .738 OPS, finally registering a positive WAR and above-average OPS+ with the White Sox… barely. His 0.2 fWAR reflected the steep decline of his once-elite defense.

With age, Benintendi isn’t close to the defender he used to be, and now Chicago is left carrying a contract for a slightly above-average hitter with minimal defensive value.

It’s not completely crippling given the team’s payroll flexibility. Maybe the veteran leadership and league-average bat still hold some value. But you just know Jerry Reinsdorf is sitting in his owner’s box shaking his head every time Benintendi rolls over and sends a chopper to second base.

And that’s where this contract has truly set the White Sox back.

Reinsdorf is the kind of owner who uses deals like this as justification to avoid spending real money in free agency. It becomes the excuse. The reason the White Sox are “priced out” of free agents who command $15 million per year — which won’t even get you a mid-rotation starter in today’s market.

If Chicago wants to complement its young core with legitimate pieces, ownership has to invest. The last rebuild proved you can’t rely solely on homegrown talent and rookie deals. At some point, you need to make a splash.

Reinsdorf has always been risk-averse with long-term contracts. And when the one time he does take the plunge comes back to bite him, it reinforces every bad instinct he already has.

If the failure of the Andrew Benintendi contract becomes the reason the White Sox refuse to go to the $15 million AAV range needed to land a proven closer or a respectable first baseman — like Kenley Jansen and Ryan O’Hearn — this winter, then it’s hurting the organization in far more ways than the obvious one.