July 13: Cholowsky will sign for a record $10.35MM bonus, reports Jim Callis of MLB Pipeline.
July 11: The White Sox took the UCLA shortstop Roch Cholowsky with the first overall pick in the 2026 draft. Jim Callis of MLB Pipeline reported the news about 20 minutes before the pick was officially announced, and The Athletic’s Keith Law wrote earlier today that the Sox appear to be leaning toward Cholowsky.
It is the third time the White Sox have held the first round pick, following their selections of Harold Baines in 1977 and Danny Goodwin in 1971. Cholowsky is also the second UCLA product to go first overall, following Gerrit Cole to the Pirates in the 2011 draft.
Cholowsky has been considered the favorite to go 1-1 for a long time, though there has been recent speculation that the White Sox could turn to another top prospect such as high school shortstop Grady Emerson (whom the Rays took second overall) or Georgia Tech catcher Vahn Lackey (who went third to the Twins). The Sox ended up making the pick, although Bob Nightengale of USA Today writes that Cholowsky agreed to sign for less than the $11,350,600 value attached to the first overall pick. This savings would free up more money within Chicago’s $20,489,500 draft pool, and allow the White Sox to pursue other players seeking more slot money to shed college commitments.
Despite finishing the 2024 season with a modern-day record 121 losses, Chicago picked only 10th overall in 2025 – rules prevent all teams from receiving lottery picks in three straight seasons, and the White Sox and other non-revenue-sharing teams cannot receive lottery picks in consecutive seasons. These same rules kept the 119-loss Rockies out of the process last December, leaving the White Sox (102-loss in 2025) with the best chance of winning the draft lottery, at 27.73%.
The ping pong balls have fallen in favor of the Southerners, so the White Sox can now add Cholowsky to the core of young talent they have accumulated through draft picks, international signings, and trades. What was expected to be a surprisingly long rebuild has begun to show results, as Chicago sits atop the AL Central with a 48-45 record. Cholowsky still has three years of college ball under his belt and may not need much time in the minors, so when he arrives (perhaps as early as 2027), he may join a potentially full-time contender White Sox club.
It should be noted that Chicago’s farm system already includes a good deep crop of infield prospects, as well Colson Montgomery (first round pick in 2021) has established himself as a regular in parts of two major league seasons. Teams always draft the best player available rather than focusing on a specific need, and shortstops can be moved around the diamond as they are athletic enough to handle multiple positions. The Sox can take their time sifting through their minor league options, but with Montgomery on the horizon and Cholowsky on the horizon, it could make the White Sox more open to trading a young infield prospect for some win-now help…perhaps before the August 3 trade deadline.
Baseball America, ESPN’s Kiley McDaniel, and The Athletic’s Keith Law all ranked Cholowsky as the top prospect of the 2026 draft class, while MLB Pipeline ranked him second (behind Emerson) and Fangraphs ranked him third (behind Lackey and Emerson). Pundits all agree that Cholowsky has the glovework to stick easily and thrive in the shortstop, with his strong throwing arm drawing some praise among his defensive tools. At the plate, Cholowsky makes solid contact and more, and 20-homer production could be his niche depending on how well his raw power translates and develops against big league pitching.
