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See the full story · 1 sourcesRoch Cholowsky's road to Chicago is officially underway. | (Matt Marton/IMAGN IMAGES)
It’s go time for Roch Cholowsky.
After being selected first overall by the White Sox, Cholowsky officially began his professional career with Winston-Salem on Tuesday night. He started at shortstop and batted second for the Dash, reaching base once via a walk in five plate appearances. It wasn’t much, but there were definitely some positive signs for the 21-year-old in his affiliate debut.
Since Chicago selected Cholowsky in the MLB draft back on July 11, it’s been a whirlwind month for Chicago’s No. 1 pick. Cholowsky spent a week in the organization’s draft-eligible athletes camp in Charlotte before spending two weeks in Arizona working out and playing in Bridge League games, where he hit his first career pro home run on Saturday.
Roch Cholowsky’s FIRST bridge league homer 💪 The first overall pick in the 2026 draft ranks No. 1 in the White Sox system + No. 5 in our Top 100 📈 (🎥 @complexscout ) pic.twitter.com/0qa34nV3FG
— Baseball America (@BaseballAmerica) August 1, 2026
His performance on the field has drawn rave reviews, and the same can be said for what he’s done away from the ballpark.
Reports from inside the organization describe Cholowsky as every bit as impressive in the clubhouse as he is between the lines. He welcomed his fellow draftees to his Arizona home and even treated all 25 of them to a steak dinner. White Sox director of hitting Ryan Fuller recently said Cholowsky has a natural presence about him, and by all accounts, he has quickly earned the respect of teammates and coaches alike. As Chris Getz and the front office continue emphasizing culture throughout the organization, those leadership qualities may prove nearly as valuable as his considerable talent.
As for the debut itself, the nerves were understandable.
Cholowsky’s first professional at-bat lasted just three pitches, ending with a strikeout.
His second trip to the plate was a much better representation of the hitter the White Sox believe they drafted. With runners on first and second and one out, he patiently worked the count to 3-0, fouled off the fourth pitch with an exit velocity of 111 mph, then rolled a grounder to second on the fifth pitch. While it went into the books as an out, the quality of the at-bat was encouraging, especially after making such a quick adjustment from his first plate appearance.
He reached base for the first time as a professional in his third at-bat, drawing a six-pitch walk with a little help from a generous strike zone. In the seventh inning, he jumped on the first pitch he saw and flew out to center.
With the game tied, 2-2, in the bottom of the ninth, Winston-Salem had a chance to walk it off. With Kaleb Freeman on first with two outs, Cholowsky stepped to the plate looking for a storybook ending. Instead, he fouled off the first two pitches before striking out swinging to end the frame and push the contest to extras.
It wasn’t the dream debut every No. 1 overall pick imagines, but one night is not going to define Cholowsky’s career. If anything, Tuesday simply marked the beginning. Over the next five weeks, White Sox fans will get their first extended look at one of Chicago’s brightest young talents, and there should be plenty of memorable moments still to come.
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