2 expensive players White Sox should figure out a way to move on from this offseason

2026 was a surprising and incredible year for the Chicago White Sox, who made a run to the ALDS and won a playoff series after three-straight seasons of losing 100+ games. The backbone of the best story in baseball was the young lineup, led by breakout stars Miguel Vargas, Chase Meidroth, and Munetaka Murakami. While the future looks bright for the White Sox, who have an influx of young talent and a ton of financial flexibility, there are a few outliers on the roster– players who are expensive and don’t offer much upside. Here are two players who the White Sox should find a way to move on from this offseason if possible. 

OF Andrew Benintendi

To label Andrew Benintendi as an outfielder at this stage of his career would be generous, as he played just 11 of his 134 games this season in the outfield. It’s only been five years, but it seems like forever ago that Benintendi took home the Gold Glove, and it’s been four years since he was an AL All-Star after hitting .304 in a season. Since he signed the largest free agent contract in White Sox history prior to 2023, it’s been a bit of a perilous journey for the former first-round pick. Benintendi hit just five home runs and posted a .682 OPS in his first year in Chicago, and his batting average plummeted despite 20 home runs in 2024. 2025 was his best season with the White Sox, as he slugged 20 home runs again and this time raised his OPS+ to a slightly-above-average 104 mark. 2026 was more of the same, though the majority of his playing time came against right-handed pitching as he faded into a platoon role. 

Benintendi has one year left on his five-year deal entering 2027, and the White Sox will owe him approximately $15 million. He’s been nothing more than a league-average hitter during his time in Chicago and he has very little defensive value left, so the White Sox would love to find a way to move on from his contract if at all possible. It won’t be easy. It’s hard to see a team being willing to take on that much money in a trade for a guy with a very limited skillset, leaving the White Sox with three main options. They could keep Benintendi and continue to utilize him in a platoon DH role, but this would make it difficult to add a meaningful outfield upgrades to the roster. They could cut him, but they’d still owe him $15 million to play for somebody else. Or they could trade him for a minimal prospect return and eat most of the salary, perhaps getting $2 or $3 million in salary relief. 

There’s no easy choice here, but a decision will have to be made. 

RHP Luis Castillo 

I’ll admit, I’m one of the clowns that liked this trade a lot when the White Sox did it at the trade deadline. Luis Castillo has a long history of success in the big leagues, and I thought he was a prime candidate for a change of scenery. But his first few games in a White Sox uniform were nothing short of a disaster. Castillo posted an 8.42 ERA in nine outings for the White Sox before being mercifully put on the injured list at the end of the year with a shoulder issue. Castillo has one more year of control entering 2027, and it’s not cheap. The White Sox owe him $24 million, and there’s a vesting option for $25 million for 2028 that vests with 180 innings pitched in 2027. Fortunately, the lockout will likely prevent that, but the Sox are on the hook for his contract in 2027 and there’s little they can do about it. 

Moving Seranthony Dominguez’s $12 million in the deal for Castillo softens the blow a little bit, so the deal is essentially a one-year, $12 million contract for 2027. That’s still expensive, but not unreasonable. Trading Castillo with his poor numbers and expensive contract seems virtually impossible, and it’s hard to see the White Sox just eating $24 million here, so I think the most likely outcome is spending the offseason trying to figure out what went wrong for Castillo and seeing if they can fix it. If they can restore him back to his career norm, his contract will look much better, but after his disastrous 2026, I wouldn’t bet on it.

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