As the White Sox continue to exceed expectations and remain in the playoff picture, MLB insider Ken Rosenthal predicts what Chicago would do at a hypothetical trade deadline.
As we close out the final week of May, the Chicago White Sox find themselves in a spot few expected them to be in: the playoff picture.
The White Sox are over .500, contending in the AL Central, and currently holding a wild card spot in a middling American League. And as we get ready to cross the threshold of being one-third of the way through the regular season, the conversation is starting to shift toward the trade deadline.
There's still two months between now and then, and plenty can change. The White Sox have a gauntlet of a schedule in June and could quickly find themselves fading from the playoff race. But should this team stay afloat, and should they still be in the mix for a playoff spot come July, how will the White Sox approach the trade deadline?
MLB insider Ken Rosenthal answered that question on Tuesday during Foul Territory.
Rosenthal grouped the White Sox in with the Washington Nationals and St. Louis Cardinals, two other teams that find themselves in the playoff conversation while exceeding expectations in 2026. Just like the White Sox, both St. Louis and Washington are built around a young core, but entered the season viewing 2026 more as a rebuilding year than a true contending year.
That can present a difficult decision for a front office. Winning seasons are hard to come by. Playoff appearances are hard to come by. The White Sox should know that better than anyone. They've made the playoffs just three times (2008, 2020, 2021) since their 2005 World Series championship. And if you're closing in on the final months of the season with an opportunity to make a playoff push, it's hard not to bite and supplement your current roster.
On the other hand, the 2026 season was always supposed to be about the future and building a foundation that can lead to sustained success down the line. Trading away significant prospect capital and becoming a buyer at the deadline contradicts that long-term vision.
So according to Rosenthal, you shouldn't expect the White Sox to veer too far in either direction.
“What I would expect from those three teams, if in two months they are still kind of in contention, would be for them to buy, but not aggressively,” said Rosenthal.
“Maybe try to enhance the team in different ways, maybe add a bullpen piece here or there. Or if there's an offensive position where they might need help, maybe do that. But they're not going to deviate from their overall rebuilding plan. They are where they are, and they're not going to jump ahead simply because they've had a good start.”
“You don't go for broke and try to win a World Series in a rebuilding year,” Rosenthal continued. “I would expect the White Sox to add, but I don't expect those additions to be in a meaningful way.”
The most glaring need, to me, is in the starting rotation. If the White Sox are going to make a playoff push, they'll need pitching reinforcements via trade at some point.
The lineup has been holding its own, and positions of weakness like catcher and the outfield should improve as players return from injury (Kyle Teel, Austin Hays) or prospects come up from the minor leagues (Braden Montgomery). There may not be reinforcements coming for the pitching staff, though.
The White Sox just called up pitching prospect David Sandlin with hopes of tapping into his upside and solidifying the starting rotation, but there are so many young arms on this staff that it seems unlikely they'll all still be pitching at full strength come August and September.
So if two months go by and the White Sox are still in the playoff conversation, expect an addition via trade to the starting rotation, though it will probably be a rental veteran the White Sox can get cheap.
They won't be moving any of their top prospects or acquiring any big-ticket players with hopes of making a World Series push. Any noise that Chicago makes in 2026 is going to come down to this young core of players and the "clubhouse magic" they've got going.
