Henry Presswood was born on October 7, 1921, in Electric Mills, Mississippi. From 1948-52 Presswood played shortstop and third baseman in the Negro Leagues. During his time in the Leagues, Presswood starred for both the Cleveland Buckeyes and the Kansas City Monarchs.
After leaving professional baseball, Presswood went to work at Inland Steel, where he played fast-pitch softball. He won several trophies and also a good sportsmanship award. Presswood retired from Inland Steel after more than thirty years of employment.