Easterling was the third baseman for the 1940 through 1943 Negro National League pennant-winning Homestead Grays. A 5’9″ 175-lb switch-hitter, he generally batted fifth behind power hitters Buck Leonard and Josh Gibson. He hit approximately .315 lifetime. In 1941, he went 6-for-10 in a doubleheader sweep as the Grays defeated the New York Cubans in the league championship series. He hit .333 in the 1942 Black World Series, and partial data on the 1943 BWS shows he batted .280. He started at third base for the East in the 1940, 1943, 1946, and 1949 all-star games, and at shortstop for the West in 1937, compiling a .320 average. He led the 1949-50 Venezuelan Winter League in doubles (16) and home runs (nine) in closing out his career.