The White Sox are heading into a winter that will demand real change, and the clearest pressure point is easy to spot: starting pitching. Chicago’s deadline gamble brought in Luis Castillo, but that move has fallen flat, leaving the front office with the same problem it tried to solve in-season. If the Sox want to move closer to contender status, they’ll need arms with control, and that likely means using some of their own tradeable pieces to get there.
Andrew Benintendi looks like one of the most obvious names to monitor. He did have a fairly solid 2026 season, hitting .240/.302/.413 with 15 home runs and 78 RBIs in 141 games while sharing time with Randal Grichuk.
But the bigger picture is hard to ignore. Benintendi’s run in Chicago has not matched the five-year, $75 million contract the White Sox handed him, and his four seasons have produced just 0.5 bWAR.
His postseason production also leaves the team with little reason to keep investing in him.
There’s also the Grichuk factor. With Grichuk now a free agent, Chicago may have to decide whether it wants to keep him or stick with Benintendi.
The problem is that Grichuk has been pushed into designated hitter work because he’s been close to unplayable in left field. That makes it tough to see a clean path for him on the roster, either.
Benintendi’s contract gives the White Sox some flexibility, too. He’s owed just over $15 million in 2027, his age-33 season and the final year of his deal. That makes him a possible salary dump, but also a candidate to be part of a bigger package if Chicago wants to land a starter and take on money in the process.
Another name that could come up is Billy Carlson. When the White Sox drafted him 10th overall in the 2025 MLB Draft out of high school, the infield picture looked very different.
Colson Montgomery had not debuted yet, Miguel Vargas and Chase Meidroth had not had their breakout seasons, Munetaka Murakami had not signed, and Roch Cholowsky had not been drafted. Now the infield is crowded, and Carlson’s long-term fit is less obvious.
Carlson is still just 20, and the upside is very much there. He was billed as the best defensive shortstop prospect in decades, maybe even ever, and so far he has backed up that reputation.
In 60 minor league games, he hit .252/.380/.335, though he has not yet shown much power and has zero home runs. He is currently the No. 81 prospect in the game, which is exactly why he would be difficult to move.
But if the White Sox can turn that kind of prospect capital into a quality starter with control, Chris Getz may have no choice but to do it.
Brenton Doyle is another player who could end up in the rumor mill, even if his path there is less straightforward. Chicago acquired him from the Rockies for pitching prospect Mason Adams, and the move raised some eyebrows at the time.
Doyle had some productive stretches, posting a .258/.258/.462 line with five home runs, but his postseason bat disappeared with a .349 OPS. He was especially strong against left-handers, less so against right-handers, and his defense remained a major asset.
Still, the outfield logjam makes his role murky. The White Sox already have Braden Montgomery, Sam Antonacci, and Tristan Peters out there, and No.
27 MLB prospect Caleb Bonemer has also been working in center field, apparently with an Opening Day opportunity in mind. Doyle’s defense and occasional offense give him value, but not enough to justify keeping him around if the at-bats aren’t there.
He isn’t a free agent until after the 2029 season, so this isn’t about an expiring contract. It’s about fit. And with Chicago facing a winter full of hard decisions, Doyle could be the player who ends up squeezed out.
In Other News...
White Sox Face A Risky Murakami Decision This Winter
Munetaka Murakamis first season with the White Sox gave the club plenty to dream on, and plenty to think about. The rookie was named an All-Star and looked the part of a middle-of-the-order cornerstone at times, which is exactly why his situation has become one of the more important winter storylines for a team trying to build something sustainable.
Now the front office has to decide whether to commit to him with a major extension or entertain trade talks before the window gets any more complicated. Murakamis late-season downturn, including a quieter finish in both the second half and the playoffs, has only sharpened the stakes, leaving Chicago to weigh upside against risk as the offseason begins. [Read more 🡒]
White Sox Biggest Bats Vanished When This Guardians Series Turned Ugly
The White Sox spent a season rewriting expectations, turning the kind of summer that had too often ended in disappointment into a playoff run as a Wild Card team. They even got through the first round by knocking out the Astros, a notable step for a club that had spent recent years trying to climb back toward relevance. But once the American League Division Series shifted to Cleveland, the offense that had carried so much of the regular season never quite matched the moment.
Chicagos power core never really found its footing when the games tightened up, and that mattered against a Guardians team built to punish any lapse. Miguel Vargas, Munetaka Murakami and Colson Montgomery had been the lineups big bats during the regular season, but October asked for more than reputation and resumes. The Sox can point to the progress they made overall, but the series also left them with a familiar postseason question: when the spotlight got brightest, who in the middle of the order was going to break through? [Read more 🡒]
White Sox Prospects Are Already Forcing Early Questions About The System
The White Sox have plenty of reason to watch the Glendale Desert Dogs closely this fall, with nine prospects in the Arizona Fall League getting an early chance to show where the system stands. The group has already been part of a rocky start for Glendale, but the action has also offered a useful first look at how Chicagos younger players are handling higher-level competition, with both position players and pitchers getting meaningful run.
Among the names drawing attention are Caleb Bonemer and Colby Shelton, who have helped the offense in key spots and given the White Sox a little more to track as the AFL schedule unfolds. Glendale finally broke through for its first win after a string of losses, and for Chicago, the broader takeaway is less about the standings than about which prospects are beginning to shape the conversation around the organizations depth. [Read more 🡒]