1. OF Braden Montgomery | 22 | AA | 2026

Chicago has seen some of its prospects backslide, so the front office had to be thrilled to see Montgomery post respectable outcomes across three levels in his debut season, slashing .270/.360/.444 with 12 home runs and 14 stolen bases in 121 games. A switch-hitter at 6’2” 220 pounds, Montgomery was Boston’s first-round pick in 2024 (12th overall) but got dealt away in the Garrett Crochet trade before he even played an inning for the Bo Sox. Right field is wide open in Chicago, and while that probably shouldn’t accelerate this guy’s timeline, people have their own jobs to consider, so you never know.