from 1985 to 1986, gregory attended the u.s. naval academy where he played on the navy team that featured david robinson and advanced to the elite eight of the ncaa tournament. he then went to oakland university where he was a three-time all conference selection and in 1990 was named an academic all-american. in 1990, gregory graduated from oakland university with a bachelor of arts in secondary education. he went on to earn a master of arts in athletic administration at michigan state, graduating in 1992.