DeMaestri was drafted by the White Sox out of the Red Sox organization before being shuffled from Chicago to St. Louis, back to Chicago, and on to Philadelphia. He began a seven-year stretch as the Athletics’ starting shortstop in 1953. On July 8, 1955 DeMaestri went 6-for-6. As a utility infielder finishing up with the Yankees, he roomed with Yogi Berra.