The Chicago White Sox are focused on the playoffs right now. They play ALDS Game 2 in Cleveland on Monday evening.
But it’s also worth considering what the White Sox have accomplished and where they might be able to go in future seasons.
This was an incredible bounceback campaign for the White Sox, who won’t want to fall back into their losing ways in future seasons. Before this year, they had triple-digit losses three seasons in a row.
That means that when the offseason arrives, the White Sox will have to avoid resting on their laurels.
This will likely be a weird winter, because a pending lockout will change the rhythm of everything.
If the White Sox take the right approach, though, they can still make their team better for the 2027 season — and coming off the back of what they hope is a deep October run to add juice to their actions.
White Sox Predicted Trade
Bleacher Report’s Kerry Miller began this week with a new article examining six realistic trades for the offseason ahead.
His first idea involves the White Sox and the New York Yankees.
The deal he suggests would cost the White Sox two players: utility prospect Caleb Bonemer and Triple-A pitcher Pierce George.
In return the White Sox would get right-handed pitcher Luis Gil and southpaw Ryan Weathers.
Bonemer has promise for Chicago, but he also probably doesn’t have an infield spot in the near-term.
“In Colson Montgomery and Chase Meidroth, the White Sox already have a middle infield tandem that is arguably top five in the majors in terms of defensive proficiency, plus Miguel Vargas fresh off an All-Star season at third base—and all three of those guys are under team control through at least 2029,” Miller writes. “Recognizing this logjam (and his less-than-stellar glovework), they started giving Caleb Bonemer some reps in center field late in the 2026 season, giving him more paths to playing time in the majors after he clubbed 37 home runs in the minors this season.”
That headline-grabbing power, a 37-homer season for Bonemer, could make the sell easier for another team to make the trade.
“Using him as a trade chip could also work, though, if the return is not one, but two starters who could be middle-of-the-rotation arms for them for the next two years,” Miller writes.
Why Yankees Would Do This
Simply put, the Yankees have too much pitching.
There will be a team that takes advantage of that in the trade market this offseason. It would behoove the White Sox to be that team, rather than leaving the arms for someone else to acquire.
“Max Fried is signed through 2032,” Miller writes to begin breaking down the Yanks’ pitching staff. “Cam Schlittler won’t hit free agency for the first time until after the 2031 campaign. And both Gerrit Cole and Carlos Rodón are signed through 2028. The Yankees also have four more years of Will Warren, two years left on both Luis Gil and Ryan Weathers, one more season of Clarke Schmidt and two MLB-ready 23-year-olds in Elmer Rodríguez and Carlos Lagrange.”
Something has to give in the Bronx. The White Sox should happily help take a few pitchers off the Yankees’ hands.
White Sox Predicted to Trade for 2 Yankees Pitchers