He served in the United States Navy during World War II[2][3] and was the father of former longtime major league catcher Milt May.

[1] Born in Laconia, Indiana, May threw and batted right-handed, stood 5 feet 11 inches (1.80 m) tall and weighed 165 pounds (75 kg).

Tommy John, who played under May in the minor leagues, recalled "Pinky was a short man with glasses, a ruddy face, and a sunny disposition.

Finally, on October 4, 1938, May was drafted out of the Yankee system—but by the Phillies, the worst team in the National League in 1938 with a dismal outlook for their immediate future.

For the next quarter century, May managed in the farm systems of the Pittsburgh Pirates, Cleveland Indians, Cincinnati Reds and the Yankees, retiring in 1972.