The White Sox have plenty to feel good about after a wild 2026 season, but not every piece on the roster fits the next phase. Chicago surged into the ALDS, won a playoff series, and did it behind a young core that changed the feel of the entire franchise.
Miguel Vargas, Chase Meidroth, and Munetaka Murakami were right at the center of that rise. With more young talent coming and real financial room to work with, the Sox also have some costly veterans who don’t bring much upside.
Two names stand out as players Chicago should try to move off of this offseason if there’s any path to doing it.
Andrew Benintendi is the clearest example of a pricey fit that no longer makes much sense. Calling him an outfielder at this point is almost generous, since he appeared in just 11 of his 134 games in the outfield this season.
The days of the Gold Glove and the .304 season feel distant now, even if it has only been five years since the Gold Glove and four since he was an AL All-Star. Since signing the largest free agent contract in White Sox history before 2023, Benintendi’s run in Chicago has been uneven.
He hit five home runs and put up a .682 OPS in his first season. In 2024, his average slipped even though he reached 20 home runs.
His best year with the Sox came in 2025, when he again hit 20 homers and lifted his OPS+ to 104. In 2026, he mostly settled into a platoon role, with the bulk of his playing time coming against right-handed pitching.
Benintendi has one year left on that five-year deal as the White Sox head into 2027, and they’ll owe him about $15 million. He has been basically a league-average bat in Chicago, and his defensive value is close to gone.
That leaves the White Sox hoping for an exit, but the options are all messy. They could keep him and use him as a platoon DH, though that would make it tougher to add a real outfield upgrade.
They could release him and still pay the full amount. Or they could trade him for only a small prospect return while covering most of the salary, maybe trimming just $2 million or $3 million from the bill.
None of it is clean, and the team still has to choose.
Luis Castillo is the other expensive problem. The White Sox liked the trade when they made it at the deadline, and for good reason.
Castillo has a strong track record in the majors, and he looked like the kind of pitcher who could benefit from a fresh start. Instead, his early stretch in Chicago went off the rails.
He turned in an 8.42 ERA across nine outings before a shoulder issue sent him to the injured list late in the year.
His contract makes the situation even trickier. Castillo has one more year of control going into 2027, and the Sox owe him $24 million.
There’s also a vesting option for $25 million in 2028 if he throws 180 innings in 2027. The lockout is likely to keep that from becoming a real issue, but Chicago is still committed to the 2027 money.
The deal is somewhat softened by moving Seranthony Dominguez’s $12 million in the same trade, which makes it feel more like a one-year, $12 million commitment for 2027. That’s still not cheap, but it’s more manageable than the full number.
Even so, a trade looks close to impossible after what Castillo showed in 2026, and the White Sox probably can’t justify eating the full $24 million. That makes the likeliest path a winter spent trying to diagnose what went wrong and see whether they can get him back to his normal level.
If they can, the contract starts to look a lot better. After last season, though, betting on that bounce-back feels risky.
In Other News...
Colson Montgomery Gave The White Sox Hope And One Huge Concern
Colson Montgomerys 2026 season gave the White Sox plenty to build on at shortstop. He played in 153 games, led American League shortstops with 31 home runs and 87 RBIs, and finished with a 2.8 WAR, the kind of everyday production Chicago has been waiting for from the position. Even with the offensive value, his defensive metrics stayed strong enough to suggest theres a real long-term piece here, not just a power surge.
The concern, though, is how narrow the path to that production appears to be. Montgomerys contact quality dipped from his 2025 debut, his chase rate climbed, and the swing-and-miss issues were impossible to ignore over the course of the year. The White Sox can live with some strikeouts from a power-hitting shortstop, but if the swing decisions and fastball handling do not improve, the ceiling comes with a fairly obvious catch. [Read more 🡒]
Caleb Bonemer Is Giving White Sox Fans A Prospect To Watch
Caleb Bonemer has been one of the more eye-catching White Sox prospects in the Arizona Fall League, where his tools have shown up in a way that gives the organization something tangible to point to this fall. He has been standing out with his blend of raw power and speed, the sort of athletic package that tends to get noticed quickly when prospects are trying to make their case in a showcase setting.
Bonemer also turned in a big game for Glendale, adding extra-base hits in a convincing win over Mesa and reinforcing why he has become a name to keep circling on the White Sox prospect map. Within the organization, some in player development are even looking at his frame and athleticism and seeing a familiar kind of upside, which only adds to the intrigue as he continues to build momentum in front of evaluators. [Read more 🡒]
Caleb Bonemer Is Giving White Sox Fans Something To Watch Closely
Several White Sox prospects have spent the fall in the Arizona Fall League, giving the organization another look at how its young players stack up against advanced competition. Caleb Bonemer has been one of the names worth following there, joining Colby Shelton, Anthony DePino, Pierce George and Mathias LaCombe on a Glendale Desert Dogs roster that has not found much traction in the standings.
The Desert Dogs have the leagues worst record and are unlikely to push into the playoffs, which has shifted the focus even more toward individual development than results. For Chicago, that makes Bonemers showing especially notable, since he has handled the assignment well while the rest of the group has produced a mixed bag, with some players getting more out of the experience than others. [Read more 🡒]