While in College he was the captain of Washington & Jefferson's 1921 undefeated football team, which played to the only scoreless tie in the history of the 1922 Rose Bowl against the California Golden Bears.

He was one of the 11 players who played in the entire game in which Washington & Jefferson held the Golden Bears to only 49 yards rushing, two first downs, and no pass completions.

[1] Stein was named the game’s Most Outstanding Player and was inducted into the Rose Bowl Hall of Fame in 1991.

[2] Stein made his professional debut in the National Football League (NFL) in 1922 with the Toledo Maroons.

He played for Toledo, Canton Bulldogs, Frankford Yellow Jackets, and the Pottsville Maroons over the course of his four-year career.