The White Sox have reportedly promoted top outfield prospect Braden Montgomery to High-A Winston-Salem, per Chase Ford of MILB Central. This promotion marks a significant milestone in Montgomery’s development and further cements his status as one of the organization’s most promising prospects.
Montgomery’s Top Prospect Status
Montgomery, 22, was one of the centerpieces the White Sox received from the Boston Red Sox in the Garrett Crochet trade this past offseason. The switch-hitting outfielder immediately became one of the best prospects in the White Sox organization. He ranks as the #5 prospect in the White Sox farm system and the #51 prospect in the sport per MLB.com. Montgomery’s inclusion in the trade gave the White Sox something they sorely lacked: a dynamic outfielder who can impact the game with his bat and glove.
Strong Start To 2025
Montgomery immediately proved why the White Sox coveted him as part of the return for Crochet. Because an ankle injury prevented him from making his professional debut in the Red Sox organization last year, he began the 2025 season with the Low-A Kannapolis Cannon Ballers. He quickly proved that Low-A pitchers were not much of a challenge for him. Montgomery slashed .304/.393/.493 with four doubles, three home runs, and six stolen bases in 84 plate appearances over 18 games with Kannapolis. He also walked at nearly a 12% clip and posting a 142 wRC+.
He also showcased his defensive versatility, playing all three outfield positions in Kannapolis. While the ankle injury he suffered in college was significant, his performance this season indicates that he is fully healthy now and his injuries are a thing of the past.
Potential Timeline To Chicago
With his promotion to High-A, it is now easier to project Montgomery’s timeline to Chicago. Assuming he continues developing at a normal pace, Montgomery will likely spend most of the 2025 season at Winston-Salem. It is also within reason that he could finish with Double-A Birmingham by the end of the year. This timeline would likely have him begin the 2026 season with Birmingham with a promotion to Triple-A Charlotte in the cards by midseason. It is not inconceivable that we could see Montgomery in Chicago by the end of 2026 at his current pace.
Name To Watch
Braden Montgomery figures to be at the forefront of the White Sox plans moving forward. Not only is he one of the organization’s top position player prospects, but he arguably has the most upside. He offers a rare blend of power, on-base skills as a switch hitter, and massive arm strength. Today’s promotion has gotten him one step closer to Chicago. He is a prospect worth keeping an eye on moving forward.
