After a successful career at the high school level, he served as the head coach of the University of Maryland football team from 1969 to 1971. Lester was the school's fourth head coach in five years, and compiled a 7–25 record during his tenure. He was fired after the 1971 season when Maryland finished at the bottom of the Atlantic Coast Conference for the second consecutive year. Lester returned to coach interscholastic football at Paint Branch High School and Magruder High School. His teams won three Maryland state championships.