The White Sox have gone all-in on the youth revolution, and as a result, most of the team’s players are still on rookie deals. Entering 2026, just three players – Andrew Benintendi, Martín Pérez, and Luis Robert Jr. – are on multi-year, multi-million contracts. Fortunately, the White Sox hold the pursestrings with Pérez and Robert, each relying on the team to pick up an option for 2026. Unfortunately, all three of these players are holding Chicago back from climbing out of the cellar.
In 2025, Benintendi cobbled together his best season since signing a five-year, $73 million deal with the White Sox prior to 2023. He slugged 20 home runs, including five during Chicago’s September surge, for the second straight year. Still, Benintendi is likely to regress in 2026; his barrel rate was far outside of the norm for him, and he became far more likely to chase pitches outside the zone.
The White Sox have very little money tied up in long-term deals. Unfortunately, the players that are under contract aren’t paying off.
At 31 years old, Benintendi is losing a step on the basepaths and in the field. The former Gold Glover contributed a -10 fielding run value in 2025. For a player earning $17.1 million, that isn’t going to be good enough. Not to mention, the White Sox have top prospect Braden Montgomery moving swiftly through the Minors, and outfield/first base prospect Caden Connor is getting reps in the Arizona Fall League. I wouldn’t be surprised to see Benintendi hanging around while the younger guys mature, but sooner or later, his contract will be too glaringly overpriced to carry.
Fellow outfielder Robert is an even trickier spot. The White Sox seem poised to execute his club option for $20 million, making him the highest paid player on the team. Robert, though, didn’t do much to entice other clubs into a trade, posting a .223/.297/.364 line in 2025. He ended the season on the IL and other executives reportedly view the White Sox picking up the option as “unfathomable.” At the end of the day, the question becomes is it worth it to pay Robert $20 million to play mediocre baseball in Chicago (or worse, to sit on the injured list), or to pay Robert $2 million to play elsewhere and get nothing in return?
Pérez also landed on the IL in September and missed considerable time early in the 2025 season. He will be 35 as the 2026 season begins. His greatest asset has been his ability to eat innings, so if the White Sox pick up his mutual option for 2026 and he remains injury prone, the decision could be one of the biggest blunders of the offseason.