All Eyes on Cholowsky as White Sox Prepare for First Overall Pick

The Chicago White Sox are on the clock. On Tuesday, the White Sox found themselves winners in the draft lottery, securing the first overall pick in the 2026 MLB Draft. It marks the first time the White Sox have had the first overall pick since 1977, when the club selected future Hall of Famer Harold Baines. 

Now the fun begins. The early favorite to go No. 1 is UCLA shortstop Rosh Cholowsky. But selecting Cholowsky could force some positional reshuffling. If the White Sox take him, it would be their fourth shortstop drafted in the first round in the past six years.

Colson Montgomery, the club’s 2021 first-rounder, impressed last season at shortstop, hitting 21 homers in just 71 games. Defensively, he also displayed excellent range. His 7 Outs Above Average ranked in the MLB’s 92 percentile. 

Montgomery can play third base as well, which could increase pressure on Miguel Vargas and Lenyn Sosa, the current favorites to handle the hot corner. The White Sox could trade Sosa this offseason to clear space, but that would push Vargas to first base once Cholowsky is ready for the majors.

The decision gets even more complicated when you consider the team’s recent draft history. The White Sox selected shortstop Billy Carlson in the first round last year and Jacob Gonzalez in 2023. Gonzalez posted modest offensive numbers in Double-A and Triple-A last season, while Carlson is already regarded as a polished defender, with some scouts grading his arm strength and glove as high as 70 on the scouting scale.

However, the White Sox can make a strong argument for drafting the best player available, even if it isn’t a position of need. Cholowsky turns 21 in April and appears to be close to MLB-ready, which could give the White Sox lineup a much-needed boost.  

Baseball America calls him “one of the best college shortstops the draft has seen in years,” while MLB Pipeline went as far as to say that he could be the best “all-around college shortstop in 20 years.”

Last season, Cholowsky posted a 1.190 OPS for the Bruins with 23 homers and is considered a consensus first overall pick, unlike last year’s draft, which was filled with younger high school prospects. 

Regardless of who the White Sox pick it finally feels like the team’s luck is turning around. Despite losing a record-setting 121 games in 2024, the White Sox found themselves being able to pick no higher than 10th, due to the league’s anti-tanking” rules, which prevent non-revenue sharing teams from getting consecutive lottery picks. After taking Hagen Smith with the fifth overall pick in 2024, they were automatically ineligible for a top 10 selection. 

The disastrous 2024 season left fans with little reason for optimism. The team was coming off a long rebuild that produced just two playoff wins, one in the 2020 Wild Card Round and another in the 2021 ALDS, before the roster unraveled amid off-field drama and consistent underperformance on the field. 

But a 20-win improvement in 2025, fueled by young talent like Colson Montgomery, Chase Meidroth, Kyle Teel, Edgar Quero, Mike Vasil, and Shane Smith, finally gave fans reason for optimism. That progress, combined with lottery luck, gives the White Sox another chance to strengthen their growing young core and expedite their rebuild.