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.

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Singer Building

The Singer Building (also known as the Singer Tower) was an office building and early skyscraper at the northwestern corner of Liberty Street and Broadway in the Financial District of Lower Manhattan, New York City, United States. Serving as the headquarters of the Singer Manufacturing Company, it was commissioned by the company's leader Frederick Gilbert Bourne and designed by architect Ernest Flagg in multiple phases from 1897 to 1908. The building's architecture contained elements of the Beaux-Arts and French Second Empire styles. The building was composed of four distinct sections. The original 10-story Singer Building at 149 Broadway was erected between 1897 and 1898, and the adjoining 14-story Bourne Building on Liberty Street was built from 1898 to 1899. In the first decade of the 20th century, the two buildings were expanded to form the 14-story base of the Singer Tower, which rose another 27 stories. The facade was made of brick, stone, and terracotta. A dome with a lantern capped the tower. The foundation of the tower was excavated using caissons; the building's base rested on shallower foundations. The Singer Building used a steel frame, though load-bearing walls initially supported the original structure before modification. When completed, the 41-story building had a marble-clad entrance lobby, 16 elevators, 410,000 square feet (38,000 m2) of office space, and an observation deck. With a roof height of 612 feet (187 m), the Singer Tower surpassed Philadelphia City Hall to become the tallest building in the world from 1908 to 1909, when it was superseded by the Metropolitan Life Insurance Company Tower. The base occupied the building's entire land lot; the tower's floors took up just one-sixth of that area. Despite being regarded as a city icon, the Singer Building was razed between 1967 and 1969 to make way for One Liberty Plaza, which had several times more office space than the Singer Tower. At the time of its destruction, the Singer Building was the tallest building ever to be demolished by its owners, a distinction it held until 270 Park Avenue was demolished in 2019.
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One Liberty Plaza

One Liberty Plaza, formerly the U.S. Steel Building, is a skyscraper in the Financial District of Lower Manhattan in New York City. It is situated on a block bounded by Broadway, Liberty Street, Church Street, and Cortlandt Street, on the sites of the former Singer Building and City Investing Building. The building was designed in the International Style by Skidmore, Owings & Merrill and completed in 1973. It is 743 ft (226 m) tall and has 54 floors. At 2.3 million sq ft (210,000 m2), each floor offers almost 1 acre (0.40 ha) of office space, making it one of the largest office buildings in New York by usable interior space. Its facade is black, consisting of a structural steel frame. South of the building is Zuccotti Park, formerly called Liberty Plaza Park. One Liberty Plaza was originally commissioned by U.S. Steel, and also housed the headquarters of Merrill Lynch. Since 2001, One Liberty Plaza has been owned and operated by Brookfield Properties.
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Liberty Street (Manhattan)

Liberty Street is a street in New York City that stretches east-west from the middle of Lower Manhattan almost to the East River. It borders such sites as 28 Liberty Street, the Federal Reserve Bank of New York Building, Liberty Tower, the Chamber of Commerce Building 140 Broadway, One Liberty Plaza, Liberty Plaza Park, the World Trade Center, Brookfield Place, Gateway Plaza, Liberty Park, and the North Cove Marina. A FDNY Firehouse, Engine Company 10 and Ladder Company 10, is located at 124 Liberty Street, directly across from the World Trade Center.
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Zuccotti Park

Zuccotti Park (formerly Liberty Plaza Park) is a 33,000-square-foot (3,100 m2) publicly accessible park in the Financial District of Lower Manhattan in New York City. It is located in a privately owned public space (POPS) controlled by Brookfield Properties and Goldman Sachs. Zuccotti Park is bounded by Broadway to the east, Liberty Street to the north, Trinity Place to the west, and Cedar Street to the south. The park was created in 1968 by Pittsburgh-based United States Steel, after the property owners negotiated its creation with city officials. It was named Liberty Plaza Park because it was situated one block south of One Liberty Plaza. The park's northwest corner is across the street from Four World Trade Center. It has been popular with local tourists and financial workers. The park was heavily damaged in the September 11 attacks and subsequent recovery efforts of 2001. The plaza was later used as the site of several events commemorating the anniversary of the attacks. After renovations in 2006, the park was renamed by its current owners, Brookfield Properties, after company chairman John Zuccotti. Starting in September 2011, the plaza became the site of the Occupy Wall Street protest camp, during which activists occupied the plaza and used it as a staging ground for their protests throughout the Financial District; this was the first protest of what became the global Occupy movement.