His football career got off to an auspicious start when, as a boy, his strict farming father would not allow him to play ball as he had chores to do. After some conversations and an event where the whole Warren High School football team showed up to the Stein farm to help with tasks so that Herb and his brother Russ could find time to practice and play, the elder Stein allowed football to be played. Herb did so well that Pitt Panthers head coach Pop Warner recruited the youngster.

We have much more on Herb Stein in two of our books found in the Pigskin Dispatch store - When Greasy Met the Wonder Coach and Marooned.

Pitt fans were beside themselves when, in 1916, they lost their All-American center Bob Peck to graduation. The team was confident, though, when Herb volunteered to switch from his fullback position to fill the void at snapper that Peck had left. Stein hardly needed much adjustment to the changes of a new position. Herb established himself as one of the school's greatest two-way players, injecting the squad enthusiasm and prompting one observer to say: "His play was a combination of the blast furnace, the open hearth and the Bessemer converter." Those are some highly complimentary remarks from a person from the Steel City! Stein's play was so good that he became a 1921 All-America selection. Herb Stein was honored to be selected for inclusion into the College Football Hall of Fame in 1967.

Herb Stein went on to play professional football. His career spanned several years in the early days of the National Football League (NFL). Following a decorated collegiate career at the University of Pittsburgh, where he was a consensus All-American center in 1920 and 1921, Stein entered the professional ranks.  

His professional debut came in 1921 with the Buffalo All-Americans. The following year, in 1922, he played for the Toledo Maroons. Stein joined the Frankford Yellow Jackets in 1924, playing as a center in all 13 games that season.  

A significant part of Stein's pro career was spent with the Pottsville Maroons. He was a member of the 1925 Pottsville team that controversially had its NFL Championship title stripped due to a disputed rules violation. He played for the Maroons from 1925 to 1928, primarily at the center position, and was a consistent presence on their offensive line. Over his six-year NFL career, Stein played in 54 games. While team accolades like the disputed 1925 championship mark his time, he also earned individual recognition, including being named a first-team All-NFL selection by the Canton Daily News and George Halas in 1922.

College Football Hall of Fame inducted interior lineman of the University of Pittsburgh.