Never much of a hitter, May earned the catching job in Pittsburgh in 1967 with his strong defense. He kept it until July 14, 1969, when he crashed into the dugout in Montreal’s Jarry Park. On the way to the hospital, his ambulance was hit by another vehicle, and his right shoulder was injured. Replaced by rookie Manny Sanguillen, May was subsequently sent to Kansas City with shortstop Freddie Patek and pitcher Bruce Dal Canton in a six-player deal following the 1970 season. Often disabled, he struggled against AL pitchers in part-time duty, but fielded .997 in 1971.