White Sox Land No. 1 Pick in 2026 MLB Draft - and the Future Just Got a Lot More Interesting
For the first time since 1977, the Chicago White Sox are on the clock with the first overall pick in the MLB Draft. That year, they took Harold Baines - a future Hall of Famer. Now, nearly five decades later, they’re back in that same position, staring down a franchise-shaping decision in a draft that could accelerate their rebuild in a big way.
The White Sox entered the lottery with the best odds (27%) to land the top pick, but that hasn’t meant much since MLB introduced the lottery system. Until now, the team with the highest odds had never actually come out on top. That trend just broke in favor of the South Siders - and not a moment too soon.
Rosh Cholowsky: The Early Favorite, With a Catch
The early buzz centers on UCLA shortstop Rosh Cholowsky, a name already drawing comparisons to some of the best all-around college shortstops in recent memory. Cholowsky is coming off a monster season for the Bruins, where he posted a 1.190 OPS and launched 23 home runs - production that has evaluators calling him a near-consensus No. 1 pick. Some scouts have gone as far as to say he’s the best college shortstop in two decades.
But here’s where it gets tricky: if the White Sox go that route, it would mark the fourth time in six years they’ve used a first-round pick on a shortstop. That’s not a typo. And while drafting the best player available is often the right move - especially with a top pick - it does raise questions about how the team will juggle its infield depth chart moving forward.
A Crowded Infield Picture
Colson Montgomery, the club’s 2021 first-rounder, took a big step forward last season. He mashed 21 home runs in just 71 games and flashed elite defensive range.
His 7 Outs Above Average ranked in the 92nd percentile across MLB - a sign that he’s not just a bat-first prospect. He’s also capable of sliding over to third base, which could help create space if Cholowsky ends up in Chicago.
But that move would have a domino effect. Miguel Vargas and Lenyn Sosa, the current frontrunners for third base duties, could find themselves squeezed out. There’s already speculation that Sosa could be moved this offseason, which would potentially shift Vargas to first base - especially if Cholowsky is fast-tracked to the majors.
The White Sox also selected shortstops Billy Carlson (2025) and Jacob Gonzalez (2023) in recent drafts. Carlson has quickly built a reputation as a plus defender, with scouting grades on his arm and glove reaching 70 - elite territory. Gonzalez, meanwhile, had a solid but unspectacular year across Double-A and Triple-A, showing flashes but not quite breaking through offensively.
So, while Cholowsky might be the best player on the board, the White Sox will have to weigh his talent against the logjam they’ve created at his position. It’s a good problem to have - but a problem nonetheless.
A Turning Point After a Brutal Stretch
The White Sox are finally trending in the right direction after a brutal 2024 season that saw them lose a franchise-worst 121 games. And due to MLB’s anti-tanking rules, which prevent non-revenue sharing teams from landing top-10 picks in consecutive years, they weren’t even eligible to draft higher than 10th last year - despite the record-setting futility.
Still, they made the most of their 2024 pick, selecting left-hander Hagen Smith at No. 5.
And in 2025, things started to click. The team posted a 20-win improvement, thanks in large part to a wave of young talent finally starting to make an impact.
Montgomery led the charge, but he wasn’t alone. Chase Meidroth, Kyle Teel, Edgar Quero, Mike Vasil, and Shane Smith all contributed in meaningful ways, helping to stabilize a roster that had been plagued by inconsistency and off-field issues in recent years.
A Rebuild With Real Momentum
This first overall pick gives GM Chris Getz and his front office another high-leverage opportunity to build out the core of a team that’s starting to show signs of life. Getz has emphasized the value of premium positions - shortstop, center field, catcher - and has openly said he “loves shortstops” for their athleticism and versatility. That mindset has clearly shaped the team’s recent draft strategy, and it could very well lead them to Cholowsky in 2026.
But whether the pick is Cholowsky or someone else, one thing is clear: the White Sox are finally gaining momentum after years of false starts. The rebuild that once looked like a never-ending cycle of disappointment now has a direction, a foundation, and a spark of excitement.
For the first time in a long time, the South Side has reason to believe.