With Colson Montgomery, Caleb Bonemer, Billy Carlson, and potentially Roch Cholowsky all rising through the system, the White Sox may soon have more shortstops than positions to play them.
It’s an old philosophy among baseball scouts that you can never go wrong drafting up the middle. Catcher, shortstop, and center field are some of the most premium positions in the sport.
But when it comes to drafting young shortstops in particular, there’s an added element of versatility at play.
For years, the Chicago White Sox found themselves drafting for a specific need. They used the fourth overall pick in the 2018 draft on Nick Madrigal with the understanding that he would be a second baseman — and nothing more — at the big league level. Anticipating the eventual end of Jose Abreu’s career, the White Sox used the third overall pick in 2019 on Andrew Vaughn.
You can see how things work out when you draft strictly for need and select players who don’t offer much defensive versatility.
Lately, however, the White Sox have taken a different approach, and it’s beginning to give the organization one of the best problems possible. Chicago suddenly has “too many” talented young shortstops, and if they all continue developing at their current pace, the organization could have a tough time finding playing time for all of them.
After a dominant second half in 2025 that included 21 home runs and surprisingly strong defense, Colson Montgomery currently looks like the White Sox shortstop of the future. But is it possible someone eventually pushes Montgomery off that spot?
In the second round of the 2024 MLB Draft, the White Sox selected high school shortstop Caleb Bonemer out of Okemos High School in Michigan.
The 2025 season marked Bonemer’s first year of professional baseball, and he played at two different levels while posting a .874 OPS with 30 doubles, 12 home runs, and 29 stolen bases at just 19 years old. That performance sent Bonemer rocketing up prospect rankings. According to MLB Pipeline, he is now the No. 3 prospect in the White Sox organization and the No. 61 prospect in all of baseball.
Other outlets, such as Baseball America, are even more bullish. They already rank Bonemer as a top-30 prospect in the game, and there is belief that he could ascend into the top 10 nationally if he posts another big season in 2026.
On top of that, the White Sox used the 10th overall pick in the 2025 MLB Draft on high school shortstop Billy Carlson, who is already a top-100 prospect in his own right (MLB Pipeline No. 73). Carlson was considered the best defensive shortstop in his draft class by a wide margin, and scouts have very little doubt that he’ll stick at the position long-term while potentially developing 20-home-run power.
The White Sox also hold the No. 1 overall pick in the 2026 MLB Draft, and they are currently favored to select UCLA shortstop Roch Cholowsky, whom many scouts tout as the best college shortstop prospect of the last 20 years. Cholowsky is the type of player who would be drafted, sign with the White Sox, and immediately become a top-five prospect in the game. He could reach the big league level as soon as 2027.
To be honest, that’s only the tip of the iceberg. But even just looking at that group of four shortstops raises an interesting question: where can we realistically expect each of them to play long-term if they all pan out?
Jim Callis of MLB.com recently laid out his prediction.
Because defense at shortstop is so essential, Callis believes Billy Carlson will remain at the position long-term — assuming he hits well enough to hold down a starting job.
Colson Montgomery should have a relatively easy transition to third base if needed, especially compared to moving to the outfield. Plus, the power in his bat profiles well at a corner infield position.
Callis therefore projects Cholowsky as a long-term second baseman for the White Sox, while Bonemer could eventually transition to a corner outfield spot.
But honestly, it wouldn’t surprise me if both of those players ended up in the outfield long-term.
We see this kind of thing all the time. There’s no better example than the San Diego Padres. Their infield already features natural shortstops Xander Bogaerts and Manny Machado. Meanwhile, Fernando Tatis Jr. and Jackson Merrill were both shortstops as prospects, and now they patrol right field and center field at an elite level.
Of the group, I do think Cholowsky and Bonemer are the most likely candidates to move to the outfield. Sam Antonacci is another player I haven’t mentioned yet who could factor into the infield mix at some point during the 2026 season. But he, too, could experiment with a corner outfield role if it helps him find more regular playing time.
Like I said before, it’s a good problem to have. In fact, it might be the best possible problem to have.
It’s also a sign that the White Sox are finally doing things the right way. Instead of drafting strictly for need and scrambling to fill holes as they appear, the organization is beginning to build real positional depth.
A year ago, I thought the wave of young starting pitchers was the most exciting thing in the White Sox system. But as we get ready for the 2026 season, it might actually be the surplus of talented young shortstops that will shape the future on the South Side.