The Chicago White Sox received excellent news at the Wnter Meetings that they in fact won the draft lottery and would be granted the first overall pick in the 2026 MLB Draft. Of the lottery-eligible organizations, the White Sox had the best odds at 27.73% to land the first overall pick due to their 60-102 regular season record in 2025.
Despite coming off of the worst regular season in MLB history in 2024, the White Sox were ruled ineligible for the 2025 draft lottery due to its rules. Teams that pay into revenue sharing can’t enter the draft lottery in consecutive seasons. As an organization in a large market, the White Sox pay into revenue sharing and had the fourth overall pick in 2024, ruling them out of the 2025 draft lottery.
Fortunately for the Pale Hose, their return to the draft lottery following their third straight 100-loss season yielded them the first overall pick. It is the first time since 1977 that they will have the luxury of selecting first in the draft. It was with that pick that year that the White Sox selected Hall of Fame first baseman Harold Baines.
Roch Cholowsky could be the White Sox's next homegrown star
Fast-forward to 2026, and the White Sox once again have the opportunity to add a future star. Barring a drastic change to the top of the draft class, UCLA’s Roch Cholowsky is comfortably the favorite to end up with the White Sox as the first overall pick. A multi-tool shortstop, Cholowsky was one of the top position players in the country in 2025 and helped lead the Bruins to a World Series appearance in Omaha.
As a sophomore at UCLA, Cholowsky hit 23 home runs with a.353/.480/.710 slash line — good for a 1.190 OPS across 324 plate appearances. He brings a lethal combination of contact skills and power to the plate as well as excellent speed on the bases. Defensively, Cholowsky has just as much upside as his strong arm and advanced range earned him an NCAA Gold Glove award at shortstop. His profile as a college shortstop has drawn a lot of comparisons to Dansby Swanson, who was selected first overall by the Arizona Diamondbacks in 2015.
A number of scouts and draft analysts believed Cholowsky would have been the first overall pick in the 2025 draft had he been eligible as a sophomore. In each of the last two drafts, the favorite to be the first overall pick was not nearly as clear-cut as it is for 2026. In 2023, Paul Skenes emerged as the favorite to be the first overall pick but was not the favorite as early as December.
It has been a while since this process was as clear-cut as it is right now, and as early as it is now. As it stands, the White Sox would need a reason not to select Cholowsky on July 11, 2026 in Philadelphia.