Playing GM: 4 Moves to Complete White Sox Roster in 2026
This winter, the White Sox should be looking to make moves that'll help them improve over last year without losing sight of the big picture. Here are four that should help them do so.
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Not far removed from being a historically bad team, the framework is there for the Chicago White Sox to ascend.
Even in a year everyone knew wouldn’t spark a parade, there was a lot of excitement brewing in the Windy City in 2025. At least, much more than a traditional 60-102 season would yield.
But it’s true. The second half especially brought tons of excitement. For starters, the youth movement began to take shape. Catcher Kyle Teel and shortstop Colson Montgomery were both top-six hitters at their positions after the All-Star Break.
Teel, the 2024 first-round pick acquired from Boston for Garrett Crochet, had a 136 wRC+ after the break, a .376 on-base percentage, and eight home runs. Montgomery blossomed into a Rookie of the Year hopeful, hitting the fifth-most homers in baseball in the second half as well.
Moreover, Miguel Vargas had a strong second half, while right-hander Shane Smith made the All-Star team.
Sure, they’re still a few years away from being a real threat. But the foundation is there; there’s light at the end of the tunnel.
This represents a continuation of our “Playing GM” series. What’s been a somewhat eventful winter for the White Sox is not done. While the name of the game is still building for long-term sustainability, here are four moves this team can make to help improve from last year without losing sight of the big picture.
1. Sign a Cheap Left-Handed-Hitting Outfielder
On the show, the agreed-upon name was former Minnesota Twins and Philadelphia Phillies right fielder Max Kepler. However, Kepler’s since been suspended 80 games for violating the league’s performance-enhancing substance policy.
The price point the White Sox likely consider is something neighboring $7 million. Some options in that tier of player are Michael Conforto, Jesse Winker, and Alex Verdugo. Even though he’s going into his age-33 season, Conforto is probably the highest upside of the bunch.
With as much of a struggle as 2025 was for the veteran, he dramatically underperformed his expected metrics. He especially underperformed against fastballs, posting a .328 wOBA against a .383 expected wOBA against heaters.
He’s got some experience in right field as well, most recently in 2023 with the San Francisco Giants. So, he fits right in with Andrew Benintendi and Luis Robert Jr. in a veteran outfield on a young team. On the cheap, he could give the White Sox a strong 90 games before a summertime trade to an outfield-hungry postseason contender.
If not Conforto, maybe Kepler is still the play here. Even though no contending team would deal for a postseason-ineligible player, think of it in the same vein as signing a pitcher recovering from Tommy John Surgery. Sure, Year 1 is essentially paid time off, but Year 2 is where the value sets in.
If the White Sox gave Kepler something like two years for $14 million, $3 million coming in 2026, they’ve secured a tradeable chip next winter or the following trade deadline. Conceptually, Kepler has always been a “more than meets the eye” kind of bat.
Perhaps going to a rebuilding team in Chicago allows him to realize that potential and be ready for that next opportunity with a contender.
2. Hold on to Luis Robert Jr. For Now
It wouldn’t be a proper White Sox conversation without hitting on the veteran center fielder.
Last season was a tale of two for Robert, who looked historically bad in the first half before looking like his superstar self in the second. After the All-Star break, the 28-year-old slashed .298/.352/.456 with five home runs in 125 plate appearances.
Yes, he also dealt with injuries. Because as much as you can’t talk White Sox without touching on his tradability, you can’t talk about Robert without discussing his injury history. When he’s right, he’s one of the most exciting players in baseball. Unfortunately, him being healthy and right are too often unaligned.
Holding onto him for now in all likelihood does minimal to hurt his value and can only truly inflate it. If he’s hitting in the first half, and healthy, he’d be one of the most sought-after bats on the market. Even if he’s not hitting or healthy, there will still be interest.
He’s still a gifted defender at worst, with tremendous power from the right side. He’s not someone the White Sox need to rush out the door by any means necessary, especially with him under team control through 2027 on a club option.
3. Sign Left-Handed Reliever Danny Coulombe
Part of improving on a 60-win season is slamming the door on games you lead late. For the White Sox, fortifying their bullpen is paramount this offseason.
But when looking at their pen, especially the high-leverage guys, they’re rife with right-handers. Guys like Jordan Leasure, Grant Taylor, and Mike Vasil figure to assume a lot of high-leverage opportunities for Chicago.
Even Prelander Berroa, another righty, will surely factor into that mix when he comes back from Tommy John rehab.
For lefties, they have Brandon Eisert and Tyler Gilbert; maybe Sean Newcomb as well, but he’s projected as their No. 5 starter. Regardless, this highlights a need for another lefty reliever.
Someone like Coulombe makes a ton of sense for a few reasons. For starters, he’s going to be cheap. Even coming off of a 2.12 ERA in 2024, he only signed for $3 million with Minnesota last winter. Even if you want to treat his free agency like an extension of arbitration, giving him a significant raise still results in $5 or so million.
Second, Coulombe is among the best lefty relievers in baseball. Last season, he struggled after a midseason trade to the Texas Rangers but finished the year with a 2.30 ERA and 3.30 FIP in 43 innings.
Teams are always hungry for relief pitching during the summer months. Coulombe in a lot of ways could be one of the better arms available again next summer. Not a bad return on investment for a rebuilding team signing a 36-year-old reliever.
4. Trade Korey Lee to the Philadelphia Phillies
Even before claiming Drew Romo off waivers, the White Sox didn’t have much of a pathway to playing time for Lee.
Between Teel and fellow former top prospect Edgar Quero, the White Sox have two promising young catchers to give burn behind the dish. Lee, while still young, doesn’t fit the timeline anymore. Even though he flashed a little more as a hitter in 2025, it was only 40 plate appearances.
He’s hovered around the mid-to-low 80s in wRC+ as a high-minors catcher in recent years, and perhaps a team needy for a backup catcher gives up a dartboard throw prospect. The Phillies come to mind especially, having dealt Eduardo Tait last winter and remaining uncertainty surrounding JT Realmuto.
Right now, the Phillies two catchers on the 40-man roster are Rafael Marchán and Garrett Stubbs. Behind them, Mark Kolozsvary and Rene Pinto in Triple-A. Overall, Marchán’s been fine in parts of four seasons defensively, but there’s not much in the way of long-term sustainability at the position.
Even at 27, Lee would be the youngest catcher sniffing around the big leagues for the Phillies. With team control, and likely on the cheap, he makes a lot of sense for a veteran Phillies team.
The return? 24-year-old right-hander Jean Cabrera.
Cabrera was among the other names to watch outside the Phillies top 15 prospects after the 2024 season. In 2025, he posted a 3.81 ERA and an 11.5% strikeout-to-walk rate in 137 innings pitched. He’s intriguing, but his command was touch-and-go last season. With the White Sox recent run of developing capable starting pitching, Cabrera affords them another option in the mid-to-upper minors.
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