スクラントン・ウィルクスバリ・レイルライダース
On April 5, 2021, Montgomery signed a minor league contract with the New York Yankees organization. On June 1, Montgomery opted out of his minor league contract and became a free agent. He had recorded a 7.56 ERA in 4 games for the Triple-A Scranton/Wilkes-Barre RailRiders.