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Around 1900, the Chicago White Sox, then the city's only professional baseball team built a ball field at Pershing Road and Wentworth Avenue in the Armour Square community. By 1913, the property had passed to the Chicago Baseball League's (later the Negro National League's) American Giants, who erected a 9,000-seat grandstand there. By 1946, the ball field was gone, and the Chicago Housing Authority began building the 422-unit Wentworth Gardens public housing development on the site of the former ball field. The complex included a centrally-located community center to provide a gathering place for residents of the Wentworth Gardens Homes. In 1964, the ¿ì²¥ÊÓƵ began offering recreational programming at the community center on behalf of CHA. In 1968, the agencies formalized the relationship, with the Park District signing a lease for use of the community building and more than an acre of surrounding property. In 1969, the Park District constructed a swimming pool behind the community center. In 1991, the Park District provided new recreational opportunities to residents by adding volleyball and basketball courts, a soft surface playground, a jogging path, and a picnic area.  In 2003, the Park District entered into an agreement with the CHA to rehabilitate the fieldhouse and surrounding greenspace.

Wentworth Gardens Park and the surrounding housing development take their names from adjacent Wentworth Avenue. The street honors John Wentworth (1815-1888), one of Chicago's best-known civic leaders. Born to a prominent family, Wentworth's paternal grandfather was a member of the Continental Congress and his maternal grandfather served as a colonel under George Washington. Almost immediately after arriving from the East in 1836, Wentworth became editor of the Chicago Democrat, and quickly involved himself in the fledgling city's politics. In 1857, and again in 1860, Wentworth was elected to a one-year term as mayor. He later became the city's police chief and also served five consecutive terms in Congress. Considered one of Chicago's most flamboyant politicians, Wentworth was known as "Long John" for his six-foot-six, three-hundred-pound physique.