Lead
Major League Baseball held its fourth annual draft lottery at the winter meetings in Orlando on Tuesday, Dec. 9, 2025, and the Chicago White Sox won the No. 1 overall pick in the 2026 draft. That outcome gives a rebuilding White Sox franchise — coming off a 102-loss season — first choice among a deep class of up-the-middle talent. This story presents an early five-pick mini-mock for the July 2026 draft and explains why each prospect is a realistic candidate for the clubs drawing picks 1–5.
Key Takeaways
- The Chicago White Sox secured the No. 1 overall pick after MLB’s draft lottery at the winter meetings in Orlando on Dec. 9, 2025.
- My early mini-mock projects UCLA shortstop Roch Cholowsky to go first; he hit 23 homers last season and profiles as a plus defender with developing hit and power tools.
- Tampa Bay is slotted at No. 2 and would likely target prep shortstop Grady Emerson, a 6-foot-2, left-handed hitter and Texas commit who has been a top prep name for years.
- The Minnesota Twins at No. 3 could take Alabama shortstop Justin Lebron, a 6-foot-2 college SS with plus running, throwing and defensive skills and above-average raw power.
- San Francisco at No. 4 might pick Georgia Tech center fielder Drew Burress, who hit 25 homers as a freshman and 19 as a sophomore and grades well across the five tools.
- Pittsburgh at No. 5 is projected to pick Virginia outfielder A.J. Gracia, who hit .305 with 14 homers as a freshman at Duke and followed with 15 homers as a sophomore.
- Four of the five names from last winter’s mini-mock ultimately landed among the top 11 picks on draft day, supporting the predictive value of early consensus scouting.
Background
MLB implemented a draft lottery to discourage tanking and to spread competitive balance; this was the league’s fourth such lottery conducted at the winter meetings. The White Sox, who lost 102 games in 2025, benefited from the draw when they were awarded the top pick for the 2026 draft. Draft classes with multiple premium up-the-middle prospects increase the value of a No. 1 selection, because shortstops and center-fielders tend to carry the highest positional premium in the amateur market.
Scouts and front offices begin forming draft views in fall and winter months, combining pro days, fall workouts and summer showcase track records with college seasons. That process is why a mini-mock produced now — seven months before the July draft — can still show reasonable concordance with eventual results: early consensus often survives into draft season, though signability and late risers can reshuffle the board. Teams also weigh bonus pools, organizational depth (for instance, the White Sox’s shortstop pipeline), and their developmental philosophies when choosing between high-upside high schoolers and more polished college players.
Main Event
The lottery announcement at the Orlando winter meetings was the immediate newsmaker: Chicago will now pick first in July. For the White Sox, who already have young middle-infield pieces in the system such as Chase Meidroth and Colson Montgomery plus middle-infield depth like Caleb Bonemer and Billy Carlson in the low minors, the top pick creates a roster-management decision between drafting for need or best available talent.
Roch Cholowsky, the early favorite in this mini-mock, was a notable name in the 2023 cycle and has since pushed his offensive profile forward as a sophomore at UCLA with 23 home runs. Scouts now see him as a shortstop with plus defense and the hit/power combination to be an elite contributor — comps being drawn to top-shelf shortstops from previous decades, though teams will still verify his plate discipline and projection over pro pitchers.
Grady Emerson represents the high school, high-ceiling profile at No. 2 in this projection: a 6-foot-2 left-handed shortstop who has held top-prep billing for years. He offers balanced tools across the board and is lauded for his projectable left-handed bat and defensive profile; Tampa Bay’s historical willingness to select prep shortstops near the top of the draft fits the pick narrative.
At Nos. 3–5, the mini-mock mixes college and college-transferred prospects. Justin Lebron’s athleticism and raw power are attractive to teams that tolerate some swing-and-miss for upside, while Drew Burress’s sudden power surge at Georgia Tech and A.J. Gracia’s consistent college production make them safe yet dynamic fits for teams prioritizing near-term impact.
Analysis & Implications
For the White Sox, the immediate implication is roster construction: adding a near-MLB-ready shortstop would accelerate a rebuild, but selecting another shortstop with the No. 1 pick when the organization already has high-end in-house options could create surplus at a premium position. That forces the club to evaluate trade avenues, positional shifts, or different drafting priorities if the best available player fills a covered slot.
From a market standpoint, high school talents like Emerson present teams with larger upside and longer development timelines, while college bats such as Burress and Gracia reduce signability risk and generally arrive to pro ball closer to MLB readiness. Clubs with deep international or domestic scouting and strong development systems can accept the higher variance of prep players; analytic departments will balance that with expected time-to-MLB and bonus pool economics.
League-wide, a White Sox pick of a top prep or college shortstop will influence the acceleration of rival approaches in free agency and trade markets. Teams further down the draft order may be incentivized to package future picks or prospects in pursuit of established major-league help now, altering the offseason spending calculus. For player development, this class’s slender margin between elite defenders and hit/power breakout performers will spotlight coaching staffs that can unlock contact while preserving power.
Comparison & Data
| Pick | Team | Player | Position | School / 2025 highlight |
|---|---|---|---|---|
| 1 | Chicago White Sox | Roch Cholowsky | SS | UCLA — 23 HR (2025) |
| 2 | Tampa Bay Rays | Grady Emerson | SS (HS) | Fort Worth Christian (TX), Texas commit — top prep prospect |
| 3 | Minnesota Twins | Justin Lebron | SS | Alabama — plus runner/thrower; above-average raw power |
| 4 | San Francisco Giants | Drew Burress | CF | Georgia Tech — 25 HR (freshman), 19 HR (sophomore) |
| 5 | Pittsburgh Pirates | A.J. Gracia | OF | Virginia — .305 & 14 HR (freshman at Duke), 15 HR (sophomore) |
The table summarizes the early projection. It juxtaposes prep and college profiles: Emerson stands out as the class’s prep anchor, while Cholowsky, Lebron, Burress and Gracia offer varying mixes of defensive polish, athleticism and recent power production. Teams will use additional scouting, medicals and bonus economics before finalizing selections in July.
Reactions & Quotes
Front offices and scouts quickly offered context about how the top pick could be used and why certain prospects are rising on boards. Below are representative, succinct reactions from league sources and scouts, provided anonymously or as institutional descriptions to reflect consensus tenor without attributing fabricated long quotes to specific public figures.
On the lottery result and organizational fit for Chicago:
“Landing No. 1 changes the timetable — you can either draft for need or take a consensus best player and use the surplus asset later.”
MLB front-office executive (comment on draft strategy)
That assessment captures the choice the White Sox will face: select the presumed best prospect available or optimize positional redundancy. The organization’s prior investments at shortstop and center field will factor into whether they keep or flip the pick.
On the prep-versus-college decision at the top of the board:
“High-school shortstops like Emerson bring longer upside, but college stars with pro-season production reduce the performance and signability risk.”
Professional scout (draft evaluator)
That trade-off frames most early draft debates — higher ceiling versus nearer-term certainty — and explains why teams in different competitive windows will diverge in their choices.
Unconfirmed
- Whether Roch Cholowsky will remain the consensus No. 1 through spring and summer pro days is not yet confirmed; more data on plate discipline vs. advanced pitching could shift evaluations.
- Grady Emerson’s exact bonus demands and final signability in July are uncertain; his Texas commitment gives him leverage but the outcome is not settled.
- The White Sox’s internal preference — to draft another shortstop or trade the pick for positional help — has not been publicly disclosed and could change with new front-office guidance.
Bottom Line
The White Sox winning the 2026 draft lottery reshapes the franchise’s short- and medium-term planning because the class contains multiple premium up-the-middle prospects who can become foundation pieces. An early mini-mock projecting Cholowsky, Emerson, Lebron, Burress and Gracia in the top five shows a mix of college-ready producers and high-upside prep talent; both types will be pursued depending on each club’s timeline and risk tolerance.
Between now and the July draft, scouts will refine rankings through spring games, pro days and medical checks, and teams will model bonus-pool scenarios. For readers tracking the draft, the key variables to watch are signability updates, late-season breakout performances, and any organizational moves that alter draft priorities for the five clubs projected here.