Coach Drury played high school baseball at West Allis Central, where he was a four-year varsity starter, two-time All-Conference selection, and team captain. He went on to play college baseball at Morton College and Milwaukee Technical College, setting the school record for lowest single-season ERA at .99. He also competed in independent league baseball in the Pecos League with the Tucson Saguaros. His coaching experience includes serving as the 17U head coach at Bigler Big Time in 2021, Head JV Baseball Coach at Cedarburg High School, coaching summer camps for the Milwaukee Brewers Academy for two years, and working as a baseball trainer at Heavy Hitters Baseball Facility from 2022–2024.