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.

The City Investing Building was in the Financial District of Lower Manhattan, with frontage on Church Street to the west, Cortlandt Street to the north, and Broadway to the east. The City Investing Building had a frontage of 209 feet (64 m) on Cortlandt Street, 109 feet (33 m) on Church Street and Trinity Place, and 37.5 feet (11.4 m) on Broadway. It had a depth of 313 feet (95 m), abutting the Singer Building to the south. The site slopes down from Broadway to Church Street, so that there was a raised basement facing Church Street, which was below ground at Broadway.

The City Investing Building's northeastern section wrapped around a real estate holdout, the Gilsey Building (also the Wessels Building or Benedict Building), at the southwestern corner of Cortlandt Street and Broadway. The Gilsey Building had a frontage of 56.5 feet (17.2 m) on Broadway and 106 feet (32 m) on Cortlandt Street. The City Investing Building's original owner, the City Investing Company, held a long-term lease for the Gilsey Building, which would have eventually been demolished to make way for an addition to the City Investing Building. To the south, there was a gap of 10 feet (3.0 m) between the City Investing Building and the Singer Tower addition to the Singer Building, which was built nearly simultaneously with the City Investing Building. The narrowness of the gap was a result of a design choice by the Singer's architect, Ernest Flagg. The columns required to support the Singer Tower would have been too large to place atop the original Singer Building, at the south end of the same block near Liberty Street.

The City Investing Building was designed by Francis H. Kimball. The general contract was awarded to the Hedden Construction Company and the contract for the foundation work was given to the O'Rourke Engineering and Contracting Company. In addition, Weiskopf and Stern were consultants for the steel frame, Griggs and Holbrook were consultants for steam and electricity, and William C. Tucker was consulting sanitary engineer. The steel was made by the American Bridge Company and erected by Post and McCord. The stonework came from William Bradley & Sons; the ornamental ironwork from Hecla Iron Works; the terracotta and other tilework from the National Fireproofing Company; the plumbing from Wells and Newton; and the marble work from J. H. Shipway and Bros.

The City Investing Building's facade was divided into three horizontal sections: a base with four stories and a raised basement; a shaft with 21 stories and a full-height cornice; and a capital with six stories and an attic. There was also a cellar below the raised basement. The City Investing Building rose 486 feet (148 m) above Broadway. Sources differ on how many stories the building had. An official building brochure and the Engineering Record described the building as having 32 stories, as counted from Broadway, although this excluded the attic. The Real Estate Record and Guide described the building as rising 33 stories, as counted from Church Street, but excluding the attic. Yet another source gave the height as 480 feet (150 m) with 34 stories, including the attic.

The City Investing Building was largely shaped in an "F", with the two northward "prongs" of the "F" flanking a 40-by-65-foot (12 by 20 m) light court on Cortlandt Street. The light court rose above the second story on the Cortlandt Street elevation. A wing ran eastward to Broadway, between the Gilsey and Singer buildings. The bulk of the building, comprising the base and shaft, consisted of 25 occupiable stories above Broadway, plus a 26th story in the cornice. The "prongs" on Cortlandt Street were designed as narrow towers terminating at the 26th story. Above the Broadway wing, the 26th story was topped by a series of engaged columns with a belvedere at the center. A flat roof rose above much of the 26th story. The central section of the building, recessed from the light court on Cortlandt Street, rose six additional stories into the capital, with an ornate gable roof made of copper. A smaller gable rose to the 31st floor directly to the east.