Esherick grew up in Silver Spring, Maryland and graduated from Springbrook High School in 1974 as an all-state forward. He was a four-year basketball letterman at Georgetown from 1974 to 1978 and thereafter attended Georgetown University Law School, receiving a law degree in 1982. During his final two years of law school at Georgetown, he served as a graduate assistant to John Thompson, Jr. In 1982, Thompson offered Esherick the position of assistant coach, and along with former teammate Mike Riley, he stayed in the position for the next 17½ seasons. After abruptly resigning in January 1999, Thompson named Esherick head coach.