Back in 2021, there was a lot of hype surrounding Benny Montgomery. According to MLB Pipeline, he was the 15th overall prospect heading into the draft. Coming out of Red Land High School in Lewisberry, Pennsylvania, he excelled at both the plate and in the field. He was named the Gatorade Player of the Year in Pennsylvania. When the Colorado Rockies drafted him with the 8th overall pick, many thought they were getting a top-of-the-order bat they could build the lineup around.
But around five years after he was drafted, Montgomery’s career has not gone the way anyone thought. While many of his other draftees, like Jack Leiter, James Wood, and Max Muncy, have made the majors, Montgomery has not played higher than Double-A. He has been stuck in Hartford for the past three seasons, and he has struggled. So much so that he has decided to retire from baseball at only 23 years old. But why was Montgomery never able to put it together?
What Caused Benny Montgomery to Retire?
Montgomery’s bat was never able to translate to minor league baseball. Over his 323 minor league games he had a slashline of .249/.345/.374 with 29 home runs and 169 RBIs. But his 2025 season saw him put up the worst numbers of his career. In 83 games he slashed .201/.274/.263 with four home runs and 36 RBIs. While his slugging numbers where better in 2026, the rest of his numbers where very close to what he put up in 2025. It was clear that he was just never going to put up good numbers.
A large reason for this was Montgomery injury history. He only played over 100 games once in his career back in 2023 when he was with the Frezno Grizzles. But the injury that appeared to do the most damage was his dislocated shoulder. Back in 2024, he suffered a dislocated shoulder that cost him the entire season. He was only able to play in 11 games, and cut short the hot start he had gotten off to. It ended the potential breakout season he needed.
After that injury Montgomery was just able to put it back together. As mentioned before 2025 was the worst season of his career, which was his first season back from injury. It’s very possible that the dislocated shoulder messed up his swing. Causing him to lose the raw power he once possed and the ability to hit like he did when he was in high school. Thus crushing his confidence and never allowing him to become the player we all expected.
Although players who are drafted high flame out all the time, Montgomery story is a bit sadder. Who knows what he could have been if he had not dislocated his shoulder back in 2024.
