<P> In 1911, the building introduced a restaurant / club in the basement . It was among the first of its kind that allowed a black Jazz band to perform, thus introducing ragtime to affluent New Yorkers . </P> <P> Even before construction on the Flatiron Building had begun, the area around Madison Square had started to deteriorate somewhat . After U.S. Realty constructed the New York Hippodrome, Madison Square Garden was no longer the venue of choice, and survived largely by staging boxing matches . The base of the Flatiron became a cruising spot for gay men, including some male prostitutes . Nonetheless, in 1911 the Flatiron Restaurant was bought by Louis Bustanoby, of the well - known Café des Beaux - Arts, and converted into a trendy 400 - seat French restaurant, Taverne Louis . As an innovation to attract customers away from another restaurant opened by his brothers, Bustanoby hired a black musical group, Louis Mitchell and his Southern Symphony Quintette, to play dance tunes at the Taverne and the Café . Irving Berlin heard the group at the Taverne and suggested that they should try to get work in London, which they did . The Taverne's openness was also indicated by its welcoming a gay clientele, unusual for a restaurant of its type at the time . The Taverne was forced to close due to the effects of Prohibition on the restaurant business . </P> <P> In October 1925, Harry S. Black, in need of cash for his U.S. Realty Company, sold the Flatiron Building to a syndicate set up by Lewis Rosenbaum, who also owned assorted other notable buildings around the U.S. The price was $2 million, which equaled Black's cost for buying the lot and erecting the Flatiron . The syndicate defaulted on its mortgage in 1933, and was taken over by the lender, Equitable Life Assurance Company after failing to sell it at auction . To attract tenants, Equitable did some modernization of the building, including replacing the original cast - iron birdcage elevators, which had cabs covered in rubber tiling and were originally built by Hecla Iron Works, but the hydraulic power system was not replaced . By the mid-1940s, the building was fully rented . </P> <P> When the U.S. entered World War I, the Federal government instituted a "Wake Up America!" campaign, and the United Cigar store in the Flatiron's cowcatcher donated its space to the U.S. Navy for use as a recruiting center . Liberty Bonds were sold outside on sidewalk stands . By the mid-1940s, the cigar store had been replaced with a Walgreens drug store . During the 1940s, the building was dominated by clothing and toy companies . </P>

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