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Who’s On Short: Which White Sox Prospect Could Claim Coveted Position?

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The post Who’s On Short: Which White Sox Prospect Could Claim Coveted Position? appeared first on Sox On 35th.

As spring training dawns, Korey Lee, Derek Hill, and Everson Pereira will fight for the final spots on the White Sox bench. Jedixson Paez, Tyler Gilbert, and Wikelman González will be among those trying to find their place in the bullpen.

Colson Montgomery, however, seems to have shortstop on lockdown in 2026.

But what about seasons beyond?

Montgomery’s ability to man shortstop long-term has been in question since his draft day in 2021. Because of his large frame, many scouts projected the infielder to transition to third base eventually. 

In his rookie campaign, the shortstop impressed defensively both by the eye test and advanced metrics, clouding what’s shaping up to be an already complicated infield log-jam. 

If the Sox infield talent all pans out (a big if), who could find their name penciled in at “6” a few seasons from now? 

Colson Montgomery

Montgomery gave a glimpse of his defensive potential in his very first MLB start. Against the Rockies, the rookie snared a Ryan Ritter flare in a highlight-reel play. 

Time and time again, the shortstop showed off his range and strong arm to quash doubts about his present ability to man the position. 

Even the analytically inclined crowd would have to agree that Montgomery’s rookie campaign was a defensive success. 

His seven defensive runs saved ranked eighth-best among shortstops this season. He accomplished this in just over 500 innings at the position, several hundred fewer than each of the seven players ahead of him. Montgomery also ranked inside the top ten in both Outs Above Average (6) and Statcast Fielding Run Value (6). 

To help Montgomery’s case, one of his long-time comps – Corey Seager – has been able to stick at shortstop for eleven seasons. Seager, in fact, ranked third in the league with 16 DRS this past season. 

All signs point to Montgomery being able to make a career out of being a shortstop, but he might have some competition in the near future. 

Roch Cholowsky (UCLA)

The Sox future shortstop might not even be a member of the organization yet. Even with a full season of college baseball still to be played, UCLA shortstop Roch Cholowsky seems destined to hear his name called first on draft night. 

Cholowsky took home the ABCA/Rawlings Gold Glove last season after posting a .978 FLD%, and he has continued to impress with his glove early this year. Cholowsky made a series of tough plays in UCLA’s series against UC San Diego, showing off both his athleticism and range. 

According to MLB Pipeline, Cholowsky profiles as a plus defender with a plus arm. He’s not particularly fast, but has good instincts that provide him with some extra range. 

Cholowsky certainly has the tools to stick at shortstop long term, but if he does end up joining the Sox system this summer, he’ll be far from its best defender at the position. 

Billy Carlson

The Sox first round pick from last season has yet to appear in a game of affiliated ball, but has already drawn high praise for his defensive prowess. 

Earlier this year, MLB Pipeline polled over 40 front office executives about prospects, and 14% tabbed Billy Carlson as the best defensive prospect in baseball. The shortstop finished second in the poll, behind just Pittsburgh’s Konnor Griffin (32.6%).

MLB Pipeline also notes that several scouts believe Carlson to be the best defensive prep shortstop they’d ever seen.

“He is a wizard at shortstop,” said Keith Law on The Athletic’s Rates & Barrels Podcast. “I remember seeing him this (past) spring. … You just don’t see teenagers make plays like that.”

His 70-grade fielding comes from his strong instincts, range, and arm, the latter of which allowed him to touch 97 MPH as a pitcher. 

There are questions surrounding Carlson’s hitting, specifically his stance and swing. If he’s able to make consistent contact, there’s no reason he can’t become the “surefire Gold Glover” that MLB Pipeline predicts him to be. 

Caleb Bonemer

The arrival of Carlson may signal a permanent end to Caleb Bonemer’s time at shortstop. The writing was already on the wall for Bonemer: after receiving a promotion to High-A Winston-Salem at the end of August, he played just one of his eleven games at short. 

Bonemer isn’t overly impressive in the field, but has earned praise for his soft hands and strong arm. Among a group that potentially boasts three plus defenders, however, he’s unlikely to ever win the day at shortstop. His defensive future could be at third, second, or even left field, according to Fangraphs.

Bonemer’s true strength lies with his bat, which has earned him top-50 prospect rankings from various publications. His offensive potential could make Bonemer’s move away from shortstop, a more defensive-minded position, a much easier decision. 

Don’t Forget About…

Kyle Lodise

Kyle Lodise spent every one of his 232.1 defensive innings at shortstop this season, performing admirably for Winston-Salem. He’s proven capable of making highlight-reel plays, as well.

The Sox 2025 third-round pick has a high floor overall, but his average range and arm strength could mean a move to second base is in his future. 

Jacob Gonzalez

It’s now or never for Jacob Gonzalez. Despite reaching Charlotte last season, the former first-round pick has never posted an OPS above .652 in any of his seasons as a member of the organization. He’s shown flashes of strong offensive production at times, but has lacked any consistency. 

Gonzalez has proven reliable on the field and has a strong arm, but may end up at second. He has good hands and has made impressive plays across the infield. His defensive ability is moot, however, if he doesn’t start hitting. 

William Bergolla

Entering his age-21 season, William Bergolla has a chance to be one of the youngest players to reach AAA this year. He rocked a .342 OBP across 551 plate appearances with Birmingham last year, and a fast start could lead to a promotion. 

MLB Pipeline says that Bergolla has good range and a strong arm, and he posted a .981 FLD% last year. Ultimately, Bergolla’s severe lack of power – he’s hit just one home run in 293 minor league games – means he’s unlikely to ever earn a starting job. 

The Verdict

If all four of Montgomery, Carlson, Bonemer, and (presumably) Cholowsky prove to be major league players, the Sox will have an embarrassment of riches on their hands.

In terms of who earns the lion’s share of time at shortstop, though, it’s tough to see Montgomery being uprooted any time soon. 

He’s shown that he can be one of baseball’s best defenders at the position, and while his frame is somewhat atypical for a full-time shortstop, Corey Seager’s continued defensive success is a sign that Montgomery could stick at short. 

Most importantly, the organization has expressed belief in Montgomery’s ability to man the position long-term. If he can maintain MLB-caliber offensive production, there’s no reason that he can’t play shortstop for the next decade-plus. While the slick-fielding Carlson seems most likely to give him a run for his money, Montgomery also holds the upper hand in a very important area: MLB experience.

At the end of the day, the simplest answer to the question “Who will be starting shortstop for the Sox in five years?” might just be the guy who’s already proven that he can do it. 

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Featured Image: @MLBPipeline/X (Cholowsky, Carlson, Bonemer), @MLBNetwork/X (Montgomery)

The post Who’s On Short: Which White Sox Prospect Could Claim Coveted Position? appeared first on Sox On 35th.