If Chicago secures the top selection in Tuesday’s MLB Draft Lottery, these are the names most likely to define the franchise’s future.
At next week’s MLB Winter Meetings, few teams will have as much riding on a single moment as the Chicago White Sox. That’s ironic, considering they aren’t expected to be major players for the top free agents on the market.
But on Tuesday at 4:30 p.m. CT, the MLB Draft Lottery will determine the shape of the 2026 draft order — and potentially the trajectory of the White Sox rebuild.
Chicago enters the drawing with the best odds of any team (27.73%) to secure the No. 1 overall pick. Yet recent history suggests that having the best odds guarantees very little. The Sox could fall as far as seventh if the ping-pong balls bounce the wrong way. Even sliding to No. 3 or No. 4 could be the difference between drafting a generational superstar… or missing entirely.
Just look back at 2019, when Adley Rutschman and Bobby Witt Jr. went 1–2, leaving the White Sox to select Andrew Vaughn at No. 3. Or in 2022, when Baltimore claimed Jackson Holliday at No. 1 while Arizona settled for Druw Jones — a talented prospect who has yet to climb above High-A.
But let’s stay optimistic. Let’s assume the Sox cash in on their odds and win the top pick. Who are the early candidates to be the next face of the franchise?
Here are the players currently most likely to go 1:1 in the 2026 MLB Draft.
Roch Cholowsky, SS, UCLA
This is the name everyone keeps circling for good reason. MLB.com’s Jim Callis wrote that “Cholowsky is pretty clearly the best prospect in the Draft right now” and even called him “the most well-rounded college shortstop in 20-something years.”
This isn’t merely a high-upside college star — this is a potential generational performer who could move quickly through the minors and become the instant centerpiece of a franchise.
The 20-year-old from Chandler, Arizona hit .353 with a 1.190 OPS, smashing 23 home runs and 74 RBIs in 66 games for UCLA as a sophomore. He does pretty much everything at an elite level.
If the No. 1 pick isn’t Cholowsky, it will likely be because of one of two things:
- a team trying to save money on a signing bonus, or
- unforeseen circumstances like an injury or steep regression.
Justin Lebron, SS, Alabama
If Cholowsky stumbles, Alabama’s Justin Lebron has a real chance to reclaim the top spot among college shortstops.
Before the 2025 season, most scouts already viewed Lebron as the consensus No. 1 prospect. But his year at Alabama didn’t quite match the lofty expectations. He still hit .316 with a 1.058 OPS and 18 home runs, but his SEC OPS dipped to .857 — a noticeable drop against stiffer competition.
Even so, Lebron’s skill set is undeniable, and with another year of growth he could easily reappear in the conversation for 1:1 if he hits the ceiling evaluators thought he would last year.
Jacob Lombard, SS, Gulliver Prep (Miami, Fla.)
The son of former MLB outfielder George Lombard and brother of current Yankees prospect George Lombard Jr. (No. 25 in baseball), Jacob Lombard has the athleticism and five-tool potential associated with classic No. 1 picks.
He’s likely to stick at shortstop and may have the highest pure ceiling in the class — but he’s also a longer-term development play compared to the college options.
If teams sour on Cholowsky or Lebron, Lombard becomes a legitimate prep alternative for a team willing to dream big and bet on their development staff.
Grady Emerson, SS, Argyle (Texas) HS
Lombard might have the highest ceiling, but Grady Emerson currently ranks as the top prep prospect in the 2026 class.
The left-handed hitter continues to add strength and emerging power — the missing ingredient that could elevate him to true 1:1 consideration. As Jonathan Mayo wrote, “If he shows up in the spring a little stronger and is getting to the power more, he could even rise into the conversation for 1–1.”
If he taps into that next gear, Emerson could become the buzziest name of the spring.
The Stakes
The top of this draft class is loaded, especially at shortstop. That’s a dream scenario for a White Sox organization already stocked with young infielders like Colson Montgomery, Billy Carlson, and Caleb Bonemer — yet still in need of a long-term offensive anchor.
Cholowsky remains the ideal outcome. He’s the closest thing this class has to a “can’t miss” franchise cornerstone. Missing out on him would sting, but the Sox could still secure a future star if they stay inside the top two or three picks.
Anything lower than that would be a disaster — the kind of setback that potentially elongates a rebuild by years.
The stakes couldn’t be higher on Tuesday evening.