Original Tenants and Subsequent History
The Fuller Company originally took the 19th floor of the building for its headquarters. In 1910, Harry Black moved the company to Francis Kimball's Trinity Building at 111 Broadway, where its parent company, U.S. Realty, had its offices. They moved them back to the Flatiron in 1916, and left permanently for the Fuller Building on 57th Street in 1929.
The Flatiron's other original tenants included publishers (magazine publishing pioneer Frank Munsey, American Architect and Building News and a vanity publisher), an insurance company (the Equitable Life Assurance Society), small businesses (a patent medicine company, Western Specialty Manufacturing Company and Whitehead & Hoag, who made celluloid novelties), music publishers (overflow from "Tin Pan Alley" up on 28th Street) and other miscellaneous concerns (a landscape architect, the Imperial Russian Consulate and the Bohemian Guides Society), as well as the offices of the Roebling Construction Company, owned by the sons of Tammany Hall boss Richard Croker.
The retail space in the building's "cowcatcher" at the "prow" was leased by United Cigar Stores, and the building's vast cellar, which extended into the vaults that went more than 20 feet (6.1 m) under the surrounding streets, was occupied by the Flatiron Restaurant, which could seat 1,500 patrons and was open from breakfast through late supper for those taking in a performance at one of the many theatres which lined Broadway between 14th and 23rd Streets.
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 clentele, 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.
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.
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