Montgomery, the No. 12 overall pick in 2024 and a big part of Chicago's return from Boston in the Garrett Crochet trade, didn't make his pro debut until 2025 due to a broken ankle suffered in college. He slashed .270/.360/.444 with 12 home runs and 14 steals in 121 games across Single-A, High-A and Double-A before heading to the Arizona Fall League, where he logged a 1.161 OPS in 12 games. A patient hitter with a massive 6-foot-2, 220-pound frame, Montgomery's top long-term traits will be his OBP prowess and plus power. The talented switch hitter has a bit of a history with lower-body injuries -- he also missed over a month before reporting to the AFL due to a small fracture in his foot. It's not a big knock at this point, but it's worth tracking, given Montgomery's size. He's a natural right fielder with a cannon of an arm and could assume that spot on an everyday basis sometime this summer, assuming he handles Triple-A. Read Past Outlooks