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Denny Bentley

Chicago Cubs | P

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Scouting Report

Updated May 19, 2026

Benny Montgomery is a 23-year-old outfielder in his sixth season with the Colorado Rockies organization. The 6'5" prospect was drafted 8th overall in 2021 out of Red Land High School in Pennsylvania. He has shown consistent progress through the minor league system, hitting .313 in Low-A (2022), .251 in High-A (2023), and earning Arizona Fall League All-Star honors. As of May 2026, Montgomery is with the Double-A Hartford Yard Goats and is taking things day-by-day while managing mental health challenges related to his professional baseball career. He credits his experiences with improving his mental resilience and learning to deal with professional pressures.

Strengths

  • + Strong draft pedigree (8th overall in 2021)
  • + Consistent minor league progression through multiple levels
  • + Excellent size at 6'5" with athletic ability
  • + Strong performance in Arizona Fall League (.333/.436/.500)
  • + Named organizational minor league All-Star
  • + Demonstrated power potential with 20+ doubles in 2022 season
  • + Early success in Arizona Complex League (.340/.404/.383)

Weaknesses

  • - Currently dealing with mental health challenges requiring day-to-day management
  • - Declining batting average trend (.313 in Low-A to .251 in High-A)
  • - Limited home run production relative to draft position
  • - Groin injury history (missed time in 2022)
  • - Still in Double-A at age 23 after six seasons in system
  • - Power numbers modest for a top-10 draft pick

Injury Status: day-to-day

About

Denny Bentley is a pitcher for the Chicago Cubs.

Player Overview

Position

P

Team

Chicago Cubs