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Soon after World War II, the ¿ì²¥ÊÓƵ began a major initiative to create new parks for the first time in many years. This Ten Year Plan identified 43 sites in neighborhoods with few recreational facilities and in undeveloped areas which were starting to boom. The Park District acquired property from 1947-1955 in the Garfield Ridge neighborhood, an area which doubled in population between 1940 and 1950. Before any improvements were made, the Board of Education requested that the northeastern corner of the park be devoted to a new elementary school. The Park District sold the property to the board, and began improving the remaining parkland in 1956. By the time the Board of Education constructed John H. Kinzie Elementary School the following year, Wentworth Park included an athletic field; volleyball, basketball, horse shoe, and tennis courts; and a children's playground. The Park District added a recreation building and sun deck in 1964. In 1965, the Board of Education built the new Kennedy High School on 56th Street across from Wentworth Park. For years, the Park District has provided jointly-operated programs from both of the schools.

John Wentworth (1815-1888), a well-known early settler and civic leader, originally owned much of the land located near what became the park. Raised in New Hampshire and a graduate of Dartmouth College, Wentworth decided to head west to seek his fortune at the age of 21. He was soon hired as editor of the Chicago Democrat, and also began studying the law. He went on to serve five terms in Congress, and two terms as Mayor of Chicago. Considered one of the city's most flamboyant politicians, he was known as "Long John" Wentworth because of his six-foot-six tall, three-hundred-pound physique.