3 White Sox extension candidates team must address if 2026 trends in right direction

The White Sox first rebuild, which turned into just one division title in 2021, failed at the hands of the White Sox core. General Manager Rick Hahn put together a group of position player prospects he felt would be the team’s foundation for many years of success. He made what he believed was a financially savvy decision at the time, and signed young position players like Yoan Moncada, Eloy Jimenez, and Luis Robert Jr. to long term extensions before they’d established themselves as good major league players. These contracts ended up being a massive liability when the development stunted and the whole thing crashed and burned. 

Chris Getz has built the current iteration of the White Sox differently and hasn’t handed anyone anything before it’s been earned. But with several top prospects making their big league push, the time is going to come soon to start looking at extensions for players who have earned a long-term place on the South Side. Here are three players who can earn it with a strong 2026 season. 

1B Munetaka Murakami

Perhaps the most obvious name for this category, Murakami has brought a ton of hype with him on his trip from Japan to the states. The former NPB MVP has game-changing power, but his high strikeout rate and low in-zone contact percentage raised enough red flags for teams that he was forced to settle for a two-year deal despite much higher projections. The White Sox feel like they got a golden opportunity here and would love nothing more than for Murakami to become a superstar in Chicago. If he comes out strong in his first season, the White Sox may feel much more comfortable offering him a long-term deal and making Murakami the first baseman of the future. It may be a hefty price for Murakami, who is currently set to hit free agency again at 27 and could earn $100+ million on the open market if he performs, but if his elite power translates to the Major League level, it’ll be worth every dollar. 

SS Colson Montgomery 

2025 was a year of ups and downs for Montgomery, who began the year with Triple-A Charlotte and struggled so badly he was pulled from game action in May. After a stint in Arizona working with White Sox hitting director Ryan Fuller, Montgomery looked much more comfortable at the plate, and he made his big league debut in July. Montgomery took the league by storm, launching 21 home runs in the final 57 games of the year and a better-than-expected shortstop. The 24 year-old now enters his second season looking to pick up where he left off and establish himself as one of the star shortstops in Major League Baseball. His main area for improvement this offseason was to work on his plate discipline, and an increase to his on-base percentage could make him a true franchise cornerstone on offense. In this case, the White Sox would need to strongly consider an extension for Montgomery, who they hope to keep around as part of their team for a long time. 

RHP Grant Taylor 

It would be a bit unconventional for a team to sign a pitcher to a long term extension this early, especially one who is currently a reliever. But there’s not a single pitcher in the White Sox organization with better stuff than Grant Taylor, and I think he’s really going to make himself known to the league this season. Taylor’s goal for this season is 100 innings, which would likely require significant multi-inning work and meaningful innings. It would also put him in position to make the transition to starting in 2027 if he stays healthy. If Taylor establishes himself as a good starting pitcher, his price will skyrocket, but if the White Sox get a long term deal done after this season, they could get excellent value. The volatility of pitching in general makes long term extensions risky, but if there’s any pitcher who’s stuff I’m willing to bet on in the White Sox organization, it’s Taylor. He’s going to be a force this season, and he's worth keeping around.