One of the biggest days of the White Sox offseason is rapidly approaching. The Winter Meeting will begin in Orlando, Florida on Sunday evening, and in addition to getting an opportunity to make moves, the White Sox will learn where they’ll be picking in the 2026 MLB draft in July. The draft lottery will take place Tuesday afternoon at 4:30pm central time, and the White Sox have the highest odds of landing the top pick.
Thanks to the Colorado Rockies, Los Angeles Angels, and Washington Nationals being ineligible for the lottery, The White Sox lead the pack with a 27.73% chance at earning the top pick, with the division-rival Twins behind at 22.18% and the Pittsburgh Pirates in third at 16.81%. The Orioles and A’s round out the top five with odds under 10%.
The White Sox had the most losses in baseball in 2024, but weren’t eligible for the lottery and ended up with the 10th pick in this year’s draft, which the team used to select shortstop Billy Carlson. They’ll get a chance for redemption this year, and it’s a great year to have the top pick. UCLA shortstop Roch Cholowsky is widely considered the favorite to go first overall, and some have called him the best college prospect in years. He’s an advanced hitter with a mature approach at the plate and big power. Though he’s far from the fastest player in the draft, he’s a plus defender at shortstop with an arm that could play at third base should his team choose to move him. Cholowsky will be 21 when he’s drafted, and he has the kind of profile that should allow him to move quickly through the minor leagues. He’s as sure of a bet as there is to be an impact talent at the big league level and won’t need years to develop.
Roch Cholowsky could be the best all-around college shortstop in 20 years.
— MLB Pipeline (@MLBPipeline) December 5, 2025
Here's what's makes him our No. 1 prospect: https://t.co/acly9V17Mo pic.twitter.com/mYAzPKBoEQ
The 2026 draft class has an elite group at the top
Cholowsky is the kind of prospect that all 30 teams would sacrifice a lot for the chance to take, but which team will land him is left up to chance. The 2026 draft class is viewed strongly, so if the White Sox were to miss out on the top pick and Cholowksy, there are other excellent options. Prep infielders Grady Emerson and Jacob Lombard as well as college hitters Justin Lebron and Drew Burress are among the top group of players that may have been in consideration for the top pick in recent seasons. The White Sox are most likely to land a top five pick and would be guaranteed one of these players if so. They can, however, fall as far as the seventh pick, which would undoubtedly be a catastrophic result given the circumstances.
Tuesday afternoon will be a crucial moment in determining the trajectory of the White Sox rebuild. If the team is able to land the top pick and secure a franchise-changing talent like Cholowsky, it certainly accelerates the timeline to competing. But a lower draw in the lottery and falling back out of the elite group of players would be a major blow to a team that badly needs a talent infusion in the farm system. White Sox fans should say their prayers and hope for good luck on Tuesday. May the odds be ever in our favor.
