No matter which direction they turn in the upcoming MLB Draft, the Chicago White Sox seem to be in an excellent position to pick the next franchise-altering player.
As Chicago looks to turn the corner out of their rebuild, this draft is crucial to nail.
With the No. 1 overall pick, Chicago is expected to take UCLA shortstop Roch Cholowsky. However, a lot can change between now and July.
Elias Schuster of Sports Illustrated, as well as other outlets, deems Cholowsky as a “true five-tool prospect.”
He has been compared to former Colorado Rockies shortstop Troy Tulowitzki because of his skill set.
As of now, Cholowsky is the No. 1 draft prospect, according to MLB.com. Just seven games into the 2026 season, he is making this decision more and more apparent.
Will The Chicago White Sox Select Cholowsky?
In seven games, Cholowsky has had an absurd .393/.486/1.143 slash line. He has hit six home runs over that span, while flashing the leather at shortstop. During the 2025 season, Cholowsky hit 23 home runs with a 1.190 OPS.
The bat is obviously what has scouts salivating at his potential, but his fielding is not to be ignored.
While many experts are set on Cholowsky to be the consensus No. 1 pick, it’s still very early in the season and process.
“The comparison game can always get a little tricky, as well as establish some potentially unrealistic expectations,” Schuster wrote. “Nevertheless, the upside Cholowksy offers is undeniable, and the fact he has started the year this hot underscores that.”
But with all of Chicago’s young infield talent, especially at the shortstop position, is it really worth taking another one?
What Is Going Into This Decision?
The White Sox have prospects Caleb Bonemer and Billy Carlson making their way through the system, as well as major-leaguer Colson Montgomery at the shortstop position.
Taking Cholowsky, who may not have the defensive versatility/speed to switch positions, could impact Chicago’s future.
Carlson has one of the best defensive profiles scouts have seen from a minor-leaguer in quite some time, with plus-plus arm strength and fielding skills. As for Bonemer, the second-round pick raked in his first professional season with an .874 OPS and 29 steals.
Montgomery had an excellent rookie season, flashing elite raw power with 21 home runs in just 71 games.
The White Sox also have several second and third base prospects and major-leaguers that could be displaced by this decision.
Other Prospects in This Draft
The White Sox likely want to fast-track their rebuild with this pick by taking a major-league-ready player, or something close to it.
This could rule out the No. 2 draft prospect, Grady Emerson, due to his young age (18), not his ability.
Fellow shortstop Justin Lebron, out of the University of Alabama, could be a closer second than people think.
In eight games in 2026, Lebron has five home runs and a 1.295 OPS, with eight steals.
Back in December, MLB.com’s draft expert Jonathan Mayo took questions about the upcoming draft.
“We did get feedback from some scouts that they wouldn’t be shocked if he played his way into No. 1 pick conversations,” Mayo wrote. “He’s really talented, with four plus tools.”
Lebron’s only knock is his tendency to chase pitches out of the zone, but the rest of his tools are undeniable. He also has the speed and versatility to potentially make a move to the outfield in the future.
By no means should the White Sox let a positional logjam affect taking a potentially generational player, but there is plenty of time to see if Cholowsky is the player everyone thinks he is.
Inside White Sox’s Roch Cholowsky Decision as New Candidates Emerging for No. 1 Pick