By his senior year, Columbia was playing its games at Madison Square Garden, and finished the season with a record of 21–2.
Though he had a full scholarship at Columbia, Gregory worked as a red cap at Manhattan's Penn Station.
He helped establish the New York City Youth Board in 1947 and served on the Municipal Civil Service Commission from 1954 to 1968.
He was chairman from 1950 until 1965 of the planning board covering Harlem in the office of the Manhattan Borough President, overseeing the initiation of $400 million in public projects undertaken in that period.
[3] Gregory died at age 88 on May 11, 1994, in his Manhattan apartment due to colon cancer.