The White Sox face a pivotal offseason this winter as they try to continue their climb out of MLB's basement. The team took a big step forward by winning 19 more games in 2025 than they did in their historically awful 2024 season. But at 60-102 last year, they obviously still have a long way to go before they can compete for a postseason berth.
If the new young core headlined by Miguel Vargas, Chase Meidroth, Colson Montgomery and Kyle Teel continues to improve, the White Sox should win more games next year. If prospects like Hagen Smith and Noah Schultz make their big league debuts and stick, it'll help even more. Same can be said for a potential return from Tommy John surgery for Drew Thorpe.
A few solid transactions could be the difference between really turning the page and another year of table setting, though. Bad ones can obviously set the process back.
Here's what we want to see, and what we don't want to see:
2 dream offseason White Sox moves, 1 nightmare change
Want to See: Sign Josh Naylor in Free Agency
First base was a carousel for the White Sox in 2025. Vargas played there 63 times, Lenyn Sosa played there 42 times and Andrew Vaughn manned the position 31 times before he was traded to the Brewers. Beyond that, seven different guys played 20 games or fewer at first base.
Moving forward, there's no clear answer for the White Sox at first, and they don't need to go to the top of the market to ink a player like Pete Alonso to make a difference. By signing Naylor, the team can both plug the hole and add a reliable bat with pop to the middle of the lineup.
Naylor has been a consistent hitter since he became a regular player in Cleveland back in 2022. Over the past four seasons, he's hit .275/.336/.464 with an average of 22 homers and 94 RBI per year.
He's added an unexpected aspect to his game, too: base stealing. In 598 games before this year, Naylor had 25 career stolen bases. But in 2025, he exploded for 30 swiped bags. According to local Mariners coverage, the difference has beenextra study to pick up tendencies and a new aggressive mindset, but no special speed training. A change like that indicates Naylor could keep it up moving forward.
The Athletic predicts Naylor will command a four-year, $90 million contract, which would make him the highest paid player in White Sox history. Now's the time to spend for the White Sox, though, and since Naylor's just 28 years old, he feels like a less risky investment than some of the older players on the market.
Want to See: Bring Back Adrian Houser
The White Sox have some intriguing young arms, with guys like Shane Smith and Sean Burke. We already went over the guys who could be on the way. Yet, the group could still use another veteran to eat innings. Houser was that guy last year, but he played so well that the Rays came knocking to acquire him at the deadline.
The deal didn't work out for the Rays, as Houser's ERA ballooned from 2.10 in 11 starts with Chicago to 4.79 in 10 starts with Tampa Bay. Maybe he could regain his form with a return to the South Side? If so, he would stabilize the rotation. If not, the White Sox could opt to call up one of their young guns to take his place.
Could be a low-risk, high-reward play for the team.
Don't Want to See: Sell Low on Luis Robert Jr.
Robert Jr.'s name has been a staple in White Sox trade rumors since the team shipped off pieces of its old core like Yoan Moncada, Tim Anderson and Eloy Jimenez. But he's remained in Chicago, in part because of ill-timed injuries, in part because of elongated slumps, and in part because the White Sox remain steadfast that he can be a star player on offense, defense and the base paths.
He showed that ability for stretches of the season last year, like the month-long streak from July 8 to Aug. 8 when he slashed .355/.425/.539 with four home runs, 14 RBI and nine stolen bases. If (and, yes, it feels like a big if) he can stay healthy, he can anchor the outfield and be a cornerstone in the lineup. At 28 years old, it's not like he's at risk of being over the hill. And it might be a sunken cost fallacy, but Getz has held onto him through "sell low" opportunities before, so there's no reason to pull the trigger now.
The absolute worst thing would be seeing him rake for another squad, just like Vaughn did when he made the move to Milwaukee.