Looking east on Leonard Street toward McKim, Mead & White's Clock Tower Building, the former headquarters of New York Life Insurance Company, 346 Broadway; ca. 1977.

In 1868, the New York Life Insurance company purchased a fire-damaged property at Broadway and Leonard Street from the Appleton's publishing house, and enlisted architect Griffith Thomas to design its new headquarters. By the 1890s, New York Life had expanded domestically and internationally was in need of a larger building for its main office. The firm solicited proposals for an eastward extension of Griffith's 1870 building, selecting Stephen D. Hatch's design for an extended structure to occupy the square block bounded by Broadway, Catherine Place, Elm (Lafayette) and Leonard Streets.

Hatch — whose winning bid notably included a lower commission that his more-celebrated competitors — died just three months into construction in 1894. McKim, Mead & White took over the commission, and completed Hatch's design, with some alterations, in 1896. However, where Hatch's design was grounded in the materials and scale of the original Thomas building, New York Life and MM&W came to favor a grander statement. The original, Thomas-designed building was razed later that year.

The new design, supervised by partner William Rutherford Mead and architect Henry Bacon, associate called for a commanding, three-story pavilion and clocktower atop a new, twelve-story neo-Italian Renaissance building flush with the completed structure along Leonard Street. The updated building, complete with its signature clocktower, was completed in 1898. The clock itself was designed by the E. Howard Clock Company and installed, along with its 5,000-pound bell, in 1897.

New York Life's tenure was relatively brief: the company moved to a new, Cass Gilbert-designed headquarters on Madison Square Park in 1928, with 346 Broadway and its clocktower passing into City ownership.

In 1972, the curator Alanna Weiss, who would go on to found and direct the P.S. 1 Contemporary Art Center (now MoMA PS1), established the Clocktower Gallery in the building's top story of the former New York Life Insurance Company building. The gallery, a multidisciplinary space for exhibitions and performances by contemporary artists, operated until 2013 when the building was sold by the city.

The fate of the clocktower and its clock became the subject of litigation and intense debate Following the sale to developers Peebles Corporation and the El Ad Group, who planned to convert the tower into a multi-story penthouse apartment.

The condo conversion plan would have required the electrification of the clock — which was restored in 1980 and continues to be wound manually every week — a move initially approved by the Landmarks Preservation Commission, but later overruled by a State Supreme Court Judge. The Clock Tower's fate remains in limbo (the prospective developers are mired in court battles over project funding), but for now the massive, mechanical timepiece continues to tick away, still guaranteed to be accurate within 10 seconds per month.