In this episode, we sit down with Coach Kurt Stein, Head Football Coach at Oakdale High School in Maryland — a leader known for building one of the state’s most respected high school football programs through perseverance, discipline, and vision.
Coach Stein began his coaching career at Catoctin High School (2004–2009), where he served as Quarterbacks Coach and Head JV Coach. In 2009, his contributions helped Catoctin capture the Maryland 1A State Championship.
When Oakdale High School opened its doors in 2010, Coach Stein took on the challenge of building a football program from the ground up — starting with only freshmen and sophomores. After an inaugural JV season in 2010, Oakdale played its first varsity season in 2011, finishing 0–10. From those humble beginnings, Coach Stein has transformed the program into a powerhouse.
Over 14 varsity seasons, Oakdale has compiled a record of 102–51, including a 15–8 playoff record and Regional Championships in 2018, 2022, and 2023. The team has reached the State Championship Game three times and claimed two Maryland State Titles — the 2A Championship in 2018 (13–0) and the 3A Championship in 2023 (14–0).
Coach Stein’s leadership and dedication have not gone unnoticed. He’s been named Baltimore Touchdown Club Coach of the Year three times (2018, 2022, 2023) and was honored as the Baltimore Ravens Maryland High School Coach of the Year in 2023.
Through it all, Coach Stein has remained focused on what matters most — developing young men of character, resilience, and teamwork both on and off the field.