5 White Sox mock extensions: Who’s in line when the club invests in the future?

After Pete Crow-Armstrong inked a new long-term deal with the Cubs on Monday night, just about every Chicago sports fan began pondering the same question: Who’s Next?

Let’s take a page from wrestling legend Bill Goldberg and play Who’s Next: White Sox edition.

Munetaka Murakami

Mock deal: Five years, $100 million

It was the estimated contract Murakami was rumored to earn before he shocked the world and signed a two-year, $34 million deal with the White Sox. What if White Sox general manager Chris Getz pulled the equivalent of a reality TV show move on the Yakult Swallows and gave Mune a smaller contract to pay a lesser posting fee? Seems uncouth.

2026 Year 1: $17m
2027 Year 2: $18m
2028 Year 3: $19m
2029 Year 4: $22m
2030 Year 5: club option for $24m

Likelihood: This would likely cause a massive rift between MLB and NPB. Not only is it unlikely, but ill advised. Murakami being with the White Sox beyond 2027 will be – and should be – based on his performance over the next two years.

Colson Montgomery

Mock deal: Seven years, $63 million

Montgomery’s rookie season was like riding The American Eagle at Six Flags backwards. At least that’s what I picture it to be like, as that side is always closed up in Gurnee. He missed most of 2025 Spring Training due to back issues, slumped in Triple A and fell out of most Top 100 prospect rankings before he was sent to Arizona to re-work his swing. He looked fine when called back to Triple A and somehow, some way, bested baseball’s golden boy, Roman Anthony, in bWAR in the same 71-game sample size in 2025.

If you’re Montgomery, unless you’re concerned about the health of your back, you don’t take this deal. Similar to Crow-Armstrong, who reportedly turned down a $66 million extension last year, Montgomery could double this number with 35-plus home runs in a fuller sample size in 2026.

I also don’t see a ton of upside for the club to rush into an extension. Failed extensions can tank rebuilds, so the White Sox should have no issue proceeding with caution.

2026 Year 1 Pre-ARB: $1m
2027 Year 2 Pre-ARB: $3.5m
2028 Year 3 Pre-ARB: $4.5m
2029 Year 4 ARB-1: $8m
2030 Year 5 ARB-2: $12.5m
2031 Year 6 ARB-3: $15m
2032 Year 7 FA1: club option ($19m)

Likelihood: If Montgomery broke camp with the team last year and hit the same 21 home runs but over 130-plus games, this might be a different conversation. With the White Sox’s past extension history being littered with injury-riddled players like Luis Robert Jr., Eloy Jimenez and Yoan Moncada, I think they’ll be better off letting things play out with Montgomery for a while.

Sam Antonacci

Mock deal: Six years, $32.5 million

This is the Colt Keith deal. Keith was a fifth-round pick out of high school for the Detroit Tigers in the 2020 MLB Draft. While Antonacci is not the White Sox’s No. 1 prospect – Keith was once the Tigers’ top prospect – Getz did say the White Sox value Antonacci more than his valuation in public prospect rankings.

Antonacci displayed great defense at second base and shortstop, along with superb instincts on the base path for Team Italy in the World Baseball Classic. While he had a few highlights at the plate, the overall slash line (.105/.261/.368) left something to be desired.

Getz said Antonacci won’t make the Opening Day roster, and assuming this deal doesn’t happen, they could effectively move Antonacci hitting the free agent market to 2033 or beyond. I’d imagine the White Sox want him to prove his hit tool first against Double-A and better pitching before calling him up, let alone signing an extension. But a deal would show they believe in his leadership, determination, and athleticism.

2026 Year 1 PRE-ARB: $2.5m
2027 Year 2 PRE-ARB: $3.5m
2028 Year 3 PRE-ARB: $3.5m
2029 Year 4 ARB1: $4m
2030 Year 5 ARB2: $4m
2031 Year 6 ARB3: $5m
2032 Year 7 FA1: club option ($10m)

Likelihood: If he were closer to breaking into the majors, then this would be more likely. However, it’s unclear whether Antonacci can hit against truly elite pitching. And with Montgomery, Caleb Bonemer, Billy Carlson, Chase Meidroth, and possibly Roch Cholowsky after July, in the organization, the White Sox do not lack interior infield options.

Edgar Quero

Mock deal: Eight years, $52 million

This is based on the Keibert Ruiz contract. While some people may say tomato and think to extend Kyle Teel, I’ll say toma-toe and extend Edgar Quero. Not because of a preference for one over the other, but due to Quero’s age. Quero will still be 22 on Opening Day. He’s also qualified as a Super Two player according to Fangraphs. This designation gives Quero four years of arbitration. To avoid that typical head-aching process, the Sox and Quero could come together on an extension beforehand.

2026 PRE-ARB: $2.5m
2027 PRE-ARB: $4m
2028 ARB1: $5m
2029 ARB2: $5m
2030 ARB3: $5m
2031 ARB4: $7m
2032 FA1: club option ($10.5m)
2033 FA2: club option ($13m)

Likelihood: It’s unclear if the Sox like Teel or Quero more. Maybe after 2026, it’ll be clearer and a decision on the future catcher of the franchise will be made. Even then, Catchers aren’t a typical high-priced item for an MLB team. Only one catcher has even signed a $100m contract on the open market – J.T. Realmuto’s $115 million deal with the Philadelphia Phillies.

Roch Cholowsky

Mock deal: Eight years, $111 million

I know this may seem like a mockery of a mock. However, if Cholowsky is the White Sox’s choice with the No. 1 overall pick in the 2026 MLB Draft and his lightning-quick ETA to the big leagues holds, could the White Sox beef up their payroll with a Cholowsky extension?

I assume they would not rush their prospective top prospect to the Majors post-draft and his true ETA would be determined by his offseason and 2027 Spring Training instead. But if he’s primed to make the 2027 roster, locking him down makes sense. From Ira Gorowara’s preseason write-up on UCLA Baseball for The Athletic, Cholowsky seems like a born leader. With a likely home carved out at shortstop, even with Billy Carlson’s presence within the organization, Cholowsky could be the piece of the White Sox’s future.

2027 PRE-ARB: $2m
2028 PRE-ARB: $3.5m
2029 PRE-ARB: $5m
2030 ARB1: $10m
2031 ARB2: $13m
2032 ARB3: $16.5m
2033 FA1: club option ($26m)
2034 FA2: club option ($35m)

Likelihood: It’s tough to say. It’s not an absolute certainty that the White Sox will even draft Cholowsky. That considered, out of the options presented, an extension for Cholowsky makes the most sense. Getz says the White Sox are building, no longer rebuilding. Cholowsky could become the franchise’s cornerstone by July.