James Benbow began his journey into varsity sports as a freshman at Everett High School playing basketball, football and track & field.
As a freshman and sophomore he made it to the Basketball State Playoffs and was on the All-Tournament Team at the Northern Lebanon Tournament. During his sophomore year he threw discus and placed second at the Bedford District 5 Track & Field meet. He was selected to the Keystone State Games for basketball.
In 1989, he went to Bedford High School as a junior and was selected to the Bedford County League All-Star Team. He also placed first in discus at the District 5 Track & Field meet and placed 4th at the PIAA State Track & Field Championship, going on to set a record in discus of 178-2 . In 1990 as a senior, he placed first in discus and first in shot put at the District 5 Track & Field meet. He placed second in the discus at the PIAA State Track & Field Championship. In basketball, he became the first player in Bedford County League history to score 1,000 points and grab 1,000 rebounds during his varsity career.
After high school he went on to Indiana University of Pennsylvania, where he was a 2-year letterwinner for the IUP football team. He lettered for IUP in 1994 and 1995, and he helped his team to the Division II semifinals in 1994. He was on the PSAC West championship teams in 1993 and 1994.