Maddy English was born on February 22, 1925 in Everett Massachusetts. Maddy was the daughter of Ambrose Tobias English, a longtime Everett city official who served as Everett’s Acting Mayor from July 1947-January 1948, and Anne English. While there were no organized interscholastic sports while she attended Everett High School, Maddy involved herself in pickup games around the Boston area, eventually joining a Massachusetts softball team in 1939, who played their home games on the concrete floor of the Boston Garden when the Bruins and Celtics teams were out of town. Her stand-out athleticism at third-base caught the eye of a professional baseball scout, who invited her to a tryout at Wrigley Field in Chicago in 1943.