Henry “Hank” Presswood was born on October 7, 1921 in Electric Mills, Mississippi. A shortstop and third baseman, he played for Mill City Jitterbugs in 1936-1937 and the Denkman All-Stars in Canton, Mississippi, from 1938 to 1944.

Presswood served with the Army from February 1945 to 1947, then returned briefly to the Denkman All-Stars before joining the Cleveland Buckeyes of the Negro League. In 1952, his last year in the Negro Leagues, Presswood played for the Kansas City Monarchs.

When his baseball career was over, he played fast-pitch softball at Inland Steel, where he was employed for 30 years.

He was “drafted” by the Chicago White Sox in the Negro Leagues Player Draft, held prior to the Major League draft at Disney's Wide World of Sports Complex in Lake Buena Vista, Florida on June 5, 2008. Each Major League club drafted a surviving former Negro Leagues player, who represented every player who did not have the opportunity to play baseball in the major leagues.