City Investing Building

The City Investing Building, also known as the Broadway–Cortlandt Building and the Benenson Building, was an office building and early skyscraper in Manhattan, New York. Serving as the headquarters of the City Investing Company, it was on Cortlandt Street between Church Street and Broadway in the Financial District of Lower Manhattan. The building was designed by Francis Kimball and constructed by the Hedden Construction Company. Because of the area's sloping topography, the City Investing Building rose 32 stories above Broadway and 33 stories above Church Street, excluding an attic. The bulk of the building was 26 stories high above Church Street and was capped by a seven-story central portion with gable roofs. The building had an asymmetrical F-shaped footprint with a light court facing Cortlandt Street, as well as a wing to Broadway that wrapped around a real estate holdout, the Gilsey Building. Inside was a massive lobby stretching between Broadway and Church Street. The upper stories each contained between 5,200 and 19,500 square feet (480 and 1,810 m2) of space on each floor. Work on the City Investing Building started in 1906, and it opened in 1908 with about 12 acres (49,000 m2; 520,000 ft2) of floor area, becoming one of New York City's largest office buildings at the time. Though developed by the City Investing Company, the structure had multiple owners throughout its existence. The City Investing Building was sold to the financier Grigori Benenson (1860–1939) in 1919 and renamed the Benenson Building. After Benenson was unable to pay the mortgage, it was sold twice in the 1930s. The building was renamed 165 Broadway by 1938 and was renovated in 1941. The City Investing Building and the adjacent Singer Building were razed in 1968 to make room for One Liberty Plaza, which had at least twice as much floor area as the two former buildings combined.