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White Sox Win 2026 MLB Draft Lottery: Predicting Top 5 Picks

MLB held its fourth annual draft lottery at the Winter Meetings in Orlando on Tuesday, and the Chicago White Sox landed the top pick in the 2026 MLB Draft.

It’s still very early in the draft process, but it’s the perfect time for a quick mini-mock draft of five picks to see how things might play out in July. Four of the five players from last winter’s edition of this exercise ended up among the first 11 picks on draft day. So it’s fair to think we have a reasonable idea of ​​how the top picks will play out, although a lot can change over the next seven months.

Here are my initial predictions for the top five picks in the 2026 MLB Draft, after consulting industry sources combined with my own research.


1. Chicago White Sox: Roch Cholowsky, SS, UCLA

Cholowsky was a big name in the 2023 draft, ranking 32nd on my final board as a standout defender with solid tools but questions about his overall offensive potential as well as a high asking price. His bonus was missed and he was solid as a freshman at UCLA, then took a huge leap as a sophomore, hitting 23 home runs last season.

He’s still a standout defender, but now his (above average) hitting and (plus) power tools have developed, allowing evaluators to look back over the last decade and find lineups at the top of previous drafts, like Dansby Swanson or Troy Tulowitzki. Cholowsky currently has a pretty solid lead over the field for the top pick, but it’s not insurmountable due to the strong group of mid-tier and high-level talent in this class.

The lottery couldn’t have gone better for the White Sox after a 102-loss season, landing the top pick in a year where there is a clear preseason favorite to be the top pick. Chase Meidroth and Colson Montgomery are solid shortstop options in the major leagues with Caleb Bonemer and Billy Carlson as Top 100 guys in the minors, but Cholowsky would pose a big problem for the White Sox: too many good players at the most important position on the field.


2. Tampa Bay Rays: Grady Emerson, SS, Fort Worth Christian (Texas) HS, Texas commit

Emerson has been touted for years as the top prep prospect in the 2026 class and has held that title throughout the summer season and fall practices. He is a 6-foot-2 left-handed shortstop who projects above average to plus in almost everything on the field. He might not be really good at anything right now, but he’s still only 17, so that could change.

Given his long track record as an elite prospect and being in the draft’s most sought-after player demographic, he is a consensus talent in this draft area, even for teams that don’t normally take high school players at the top. The Rays are not that team, taking a prep shortstop in the first two rounds of each of the last three drafts; Tampa Bay also likes left-handed hitters. Emerson is the rare prep prospect who is a safer pick than the vast majority of college players, but also has more upside.


3. Minnesota Twins: Justin LeBron, SS, Alabama

Lebron was scouted as part of the loaded 2023 prep class alongside prep teammate Antonio Jimenez, who was a third-round pick of the Mets out of UCF in 2025. Lebron’s hitting ability and athleticism each took a leap upon his arrival in Tuscaloosa and the 6-foot-2 shortstop is now a plus runner, pitcher and defender with above-average raw power. His pitch selection is good, with the only question being about his strikeout ability due to worse-than-average strikeout rates last season, fueled somewhat by a bottom-up, power-oriented approach. If LeBron can find a happy medium between his swing plane, contact and power, he could challenge Cholowsky as the top pick.

The Twins haven’t been afraid of a little swing and miss if it has big upside in recent drafts, like with Billy Amick, Brandon Winokur and Quentin Young over the last three years, but they also love taking college shortstops like Kaelen Culpepper, Marek Houston and Kyle DeBarge. Lebron threads the needle of certainty given his tools and position profile, but also his untapped upside due to his contact/power balance being a bit unbalanced at the moment.


4. San Francisco Giants: Drew Burress, CF, Georgia Tech

Burress was a pick of mine in the 2023 draft, ranking 40th overall on my board (among the highest rankings among media and teams), but ultimately proved unsignable to teams that also had him in that range. He’s only 5-foot-8, so impact power wasn’t expected at the time, but he had more power than you’d think given his size, as well as a long history of hitting for average, as well as speed and centerfield defense.

Burress exploded at Georgia Tech, particularly on the power front – hitting 25 homers as a freshman, then 19 as a sophomore – fueled by now above-average raw power. He grades above average or higher in all five tools, but his approach/swing is more power-oriented than in high school, so balancing his abilities at the plate in pro ball could be the key to reaching his ceiling. The Giants have taken college players with their top three picks each of the last two years and will likely turn to the best available player from that same demographic in 2026.


5. Pittsburgh Pirates: AJ Gracia, OF, Virginia

Gracia had almost no national scout profile coming out of a New Jersey high school as a two-way player in 2023 before heading to Duke. He immediately showed scouts that he should have been considered a true pro prospect coming out of high school, hitting .305 with 14 homers as a freshman, then following that up with more walks, fewer strikeouts and 15 homers as a sophomore. Gracia transferred to Virginia after the season, following much of the Duke coaching staff.

He is currently a 6-foot-3 center/right fielder who is above average in almost everything in the batter’s box, especially his ability to lift/pull the ball in games, although his swing can become too difficult at times.

The Pirates appear to be turning the corner with Konnor Griffin and Bubba Chandler joining Paul Skenes and Co. as they also look to spend some money in free agency, so I see them leaning into the college player group that is a strength in this class.

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