[2] After graduating, Gregory spent thirty five years in baseball as a player and college coach.

He also coached college basketball for nine years and was a World War II veteran.

His career highlight came on May 26, 1933, when he defeated Red Ruffing and the host New York Yankees, 8–6, allowing one earned run in seven-plus innings while retiring Babe Ruth in five at-bats.

[1][5] Following his majors stint, Gregory returned to play on the minor league system for nine years before serving in the US Navy during World War II, from 1943 to 1945.

[6] Gregory was in charge of the basketball squad from 1947 to 1955, then he led the Bulldogs baseball team to 15 winning seasons from 1954 through 1974, including four Southeastern Conference titles (1965–66, 1970–71) and a berth to the 1971 College World Series.