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 of space on each floor.

Work on the City Investing Building started in 1906, and it opened in 1908 with about 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.

Site 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 on Cortlandt Street, on Church Street and Trinity Place, and on Broadway. It had a depth of , 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 on Broadway and 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 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.

Architecture

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 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 with 34 stories, including the attic.

Form The City Investing Building was largely shaped in an "F", with the two northward "prongs" of the "F" flanking a 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.

Facade

The five-story base was clad with light stone, while the shaft and capital were decorated with white brick and terracotta. Porcelain and enamel brick were used to reduce cleaning costs, since that type of brick did not discolor over time.

The main entrance was at Broadway and contained a semicircular-headed opening. The fourth floor was topped by a large cornice that was at the same level as the roof of the six-story Gilsey Building. Robert E. Dowling, the building's developer, hired Vincenzo Alfano to design sculptural groups for the facade.

The 5th through 25th floors contained window bays, which generally contained two or three windows on each story. The corner bays on the "prongs" facing Cortlandt Street contained one window per floor. At various points on the facade, some of the center bays on each side contained groupings of several stories, each of which contained engaged columns and balconies. There were also horizontal belt courses between several stories. The 26th floor was inside the cornice.

Structural features The City Investing Building used a steel frame with concrete-slab floors, terracotta floor arches and partitions, and interior marble work. When completed, the building was said to weigh , excluding live loads. The steel frame alone weighed . As completed, the building used 9.1 million bricks, 25,000 lighting fixtures, of terracotta, about of plaster, about of hollow tile, of marble, and about 21.8 million mosaic cubes. Also included in the building was many miles of plumbing, steam piping, wood base, picture molding, conduits, and electrical wiring. The building contained woodwork made of fireproofed mahogany.

Superstructure The superstructure consisted of a steel cage wherein the columns at every story supported the walls. The columns, in turn, sat on cast-steel pedestals, which transmitted their loads through girders and grillages. There were 89 columns on each floor, arranged in six rows. The largest column carried a load of and had a cross section of . The floors consisted of hollow-tile flat arches or concrete with cinder filling, and were surfaced with mosaic or terrazzo tiles. The distributing girders on the third story of the Broadway wing were the largest and heaviest to be used in the building; they comprised a triple girder weighing about and spanning the entire width of that wing. Portal braces and curved knee braces were included to provide wind resistance, but also contributed to the building's weight.

The exterior walls were curtain walls whose thicknesses had been prescribed by city building codes of the time. The south wall was generally thick at the base, tapering to just below the 25th floor. The other walls varied in thickness from 32 inches at the base to below the 25th floor. There were also two walls carried atop the third-floor girders, which extended to the 27th and 32nd floors.

Foundation The foundation was excavated using rectangular caissons of varying width. The pits were drilled through layers of earth, quicksand, clay, gravel, and water to a solid rock layer beneath Broadway. The main excavation was carried to below Broadway, except at the site of the boiler room, where the excavations were carried deep. Each caisson was and made of yellow pine. A steel shaft rose from each of the caissons. The underlying ground was drawn out from the caissons, and then the caissons were filled with concrete. The retaining walls of the foundation were then constructed of concrete slabs between I-beams spaced apart. The excavation involved removing of masonry and of earth, while the foundation piers used of concrete. Sections of the masonry basement floors from the previous buildings on the site were also removed in the process.

Within the foundation were placed 59 concrete piers, which carried the columns of the aboveground superstructure. The cross-sections of the piers varied, with the smallest measuring , and the largest measuring . The caissons supported foundation piers that were topped by plates with grillages of transversely laid I-beams. Most of the superstructure's exterior columns were supported on cantilevers; deep plate girders were placed over the grillages, and the cantilevers extended outward from these girders, where they supported the columns. The foundation also used distributing girders, some of which were triple girders weighing . The cellar floor was poured as a single layer of concrete, thick. This helped distribute the building loads and counteracted the upward hydrostatic pressure.

Interior

Interior spaces

The City Investing Building was one of New York City's largest office buildings at the time of its completion, with an estimated of floor area. Generally, there was more space on higher stories than on lower stories, largely because the building's elevators were staggered into three banks serving different sets of floors. The 5th through 9th floors typically had per floor; the 10th through 17th floors each had ; and the 18th through 25th floors each had . However, the 27th through 31st floors, located in the smaller "capital" of the building, typically had . On the top of the building was a luncheon club.

The entrance arch on Broadway led to a limestone vestibule about deep, which contained the main doors. Inside the vestibule was a double-height lobby running westward to the elevated Cortlandt Street station of the Interborough Rapid Transit Company's Sixth Avenue Line at Church Street. It measured tall and wide. The arched ceiling of the lobby was decorated with colorful frescoes. The lobby was clad throughout with several types of Italian marbles. Three elevator banks extended from the southern wall of the lobby. The second floor contained offices north of the lobby, and a footbridge was placed across the lobby to connect the elevators and offices.