He grew up in Warren, Ohio and attended high school at Niles McKinley High School and later Kiski Prep, located in Saltsburg, Pennsylvania. After high school, Stein attended the University of Pittsburgh and served as the team's center from 1918 until 1921. He was a consensus All-American for Pitt in both his junior and senior years and served as the team captain in 1920. He was often regarded as one of the team's greatest offensive and defensive centers. His efforts at Pitt earned him induction into the College Football Hall of Fame in 1967.