 He would later serve on the New York City Civil Service Commission and was active as a community leader in Harlem.Gregory led the Columbia Lions to a championship in the Ivy League (then known as the Eastern Intercollegiate League) in the 1930-31 season, together with teammate Lou Bender, the team's first league title.By his senior year, Columbia was playing its games at Madison Square Garden, and finished the season with a record of 21–2.