Cregar was a starting lineman who played on Holy Cross’ only bowl team, when the Crusaders faced Miami in the 1946 Orange Bowl. He spent a year at William & Mary (1942-43) before spending 18 months in the Navy during World War II. He ended up in the Navy’s V-12 program and a year at Williams College before coming to Holy Cross in 1945 and graduating in 1947. Cregar started 21 games at guard for Holy Cross in 1945 and 1946. As a senior he was a first team All-New England and All-East selection and received All-America mention. He played two years, 1947-48, as a linebacker with the Pittsburgh Steelers in the National Football League before beginning a long career with the FBI.