The son of outfielder Dave May, Derrick spent five seasons with the Cubs then spent five more with five different franchises, including the Astros for 1995 and 1996, principally as a reserve outfielder and lefthanded pinch-hitter.

The New York native batted .273 with 13 homers while in Houston. For his full career, May hit .271 with 52 home runs over ten seasons.