Nathaniel Platt Bailey (1809-1891), the namesake of both this playground and bounding Bailey Avenue, was a 19th century Bronx landowner. Born in Chateangay, New York, Bailey was the son of Judge William Bailey, one of the earliest settlers of Plattsburg. Nathaniel Bailey settled in New York City in 1824 and quickly became a successful businessman; he retired at 35. Bailey was a Vestryman in the Protestant Episcopal Church of St. James, senior Governor of New York Hospital, and in 1884, was elected president of the St. Nicholas Society of the City of New York. Bailey’s property covered a part of what is now called West Fordham, extending from Fordham Road to Kingsbridge Road and from Bailey Avenue to University Avenue. His mansion overlooked the Harlem River, and it was said that the view was so commanding that one could see the New Jersey Palisades to the west. Upon Bailey’s death, his estate was subdivided into streets and avenues; the bulk of it became the grounds of the present U.S. Veterans Medical Center.
Nearby Kingsbridge Road overlays an older Native American path that stretched from West 225th Street at Bailey Avenue to its junction with Fordham Road. The road, along with the surrounding Kingsbridge Heights neighborhood, is named after the historic King’s Bridge that once spanned Spuyten Duyvil Creek at what is now West 230th Street and Kingsbridge Avenue. Originally constructed in 1639 as a toll bridge by local landowner Vredryck Flypson, King’s Bridge was the first bridge to connect Manhattan with the mainland. Both the American and British forces used it extensively during the Revolutionary War. In 1916, Spuyten Duyvil Creek was filled in and the bridge was torn down.
Parks acquired this site, bounded by West 234th Street, West 238th Street, and Bailey Avenue, on December 12, 1950, in conjunction with the construction of the Major Deegan Expressway. Bailey Playground is one of six disconnected parks, ranging in area from about one-tenth of an acre to about four acres, that were laid out bordering the Major Deegan Expressway. Major William F. Deegan (1882-1932) was the son of Irish immigrants and studied architecture at Cooper Institute. During World War I, he served first as a staff officer of the 105th Field Artillery and later as a major with the Army Corps of Engineers under General George W. Goethals, where he oversaw the construction of army bases in the New York City area. Deegan also served as president of the Bronx Chamber of Commerce, as Mayor James J. Walker’s Tenement Housing Commissioner, and as chairman of the Mayor’s Committee for Welcoming Distinguished Guests. On April 30, 1937 Mayor Fiorello H. LaGuardia renamed the westerly approach to the Triborough Bridge the Major William F. Deegan Boulevard; when the boulevard was lengthened in 1956 it was renamed the Major Deegan Expressway.
In recent years, a series of renovations have brought new vitality to Bailey Playground. In 1997, a $170,000 renovation funded by Council Member June Eisland replaced all of the playground’s old play equipment and added new safety surfacing. In 1998 and 1999, a $120,000 capital project funded by Mayor Giuliani renovated and refurbished the playground’s handball courts.