Real estate investor John Pettit bought the building in 1889, and he hired Farnsworth to design two expansions.

The original mansard roof was demolished to allow the addition of the top four stories between 1890 and 1892, while an eleven-story annex was erected on Ann Street in 1894.

The Bennett Building is located in the Financial District of Lower Manhattan in New York City, United States.

[3] A staircase to the New York City Subway's Fulton Street station (served by the 2, ​3​, 4, ​5​, A, ​C​, J, and ​Z trains) is outside the Bennett Building's southern facade.

[23][11] In addition, it is one of two remaining Second Empire office buildings in Manhattan south of Canal Street with a cast-iron facade, the other being 287 Broadway.

[5] The ground story was initially designed as a raised basement, with each bay separated by cast-iron rusticated vertical piers.

They are designed nearly identically to the rest of the facade, with minor differences in decorative detailing, and rise eleven stories instead of ten.

The western facade of the building and the twelfth-story penthouse are designed in plain brick and faces a small light court rising above the first story.

Landau and Condit's observations found that the floors were instead carried on brick arches, set between wrought-iron beams, whose centers were spaced 5 feet (1.5 m) apart.

The beams, in turn, rested on cast-iron brackets attached to the building's brick partition walls.

[13][28] When the building was completed, elevator technology was still relatively new,[15][29] which was one possible reason for why the rent roll was smaller on the upper floors.

[23] The building had steam heating from the outset, and after the advent of electric lighting, its owners added a generating plant.

[13] James Gordon Bennett Sr. founded the New York Herald in 1835, and within ten years, it become one of the United States' most profitable newspapers.

[30][31] After moving the Herald multiple times in its first decade, Bennett Sr. bought the northwest-corner lot at Fulton and Nassau Streets in 1843.

[38] At the time of its completion, it was one of New York City's tallest buildings, towering over other structures on Nassau Street.

[39] The Bennett Building was not particularly close to either the courts of the Civic Center to the north or the financial firms physically surrounding Wall Street to the south.

[11][44] A contemporary publication stated of the sale, "The name of Pettit is in itself a sufficient guarantee of bona fide transactions so long has it been connected with honorable and upright dealing".

[11][21] The tenants of the newly expanded building included a Postal Telegraph Company branch, a United States Congress member, architects, bankers, publishers, and manufacturers.

[8] After the annex was completed, the building was said to be worth $2 million, and the New York Life Insurance Company held a $500,000 mortgage on the property.

[47] In the years following the renovation, Pettit fell into debt, and New York Life appointed a receiver to collect the Bennett Building's rents.

[5][39] That December, a controversy emerged over an unmetered water pipe in the building: the owners were found to have owed $2,550 (equivalent to $86,473 in 2023) over seventeen years, but Wilson, Isman, and New York Life would not take responsibility.

[55] Wilson's family retained ownership until at least 1919, when the New York-Tribune reported that it had been sold to a "syndicate of well-known real estate men".

[39] However, the New York City Landmarks Preservation Commission (LPC) stated that the building remained in the Wilson family's ownership through the 1940s.

[23] ENT Realty Corporation bought the building in 1995 and leased it to a consortium led by Robert Galpern.

[23] Around the same time, preservationist Margot Gayle led an effort to have the Bennett Building preserved as an official city landmark.

[14][60] In its first two decades, it had become known as an unofficial landmark of Lower Manhattan, and was described as "one of the largest and stateliest piles down-town".

[28] In 1991, Christopher Gray of The New York Times described the building as appearing to "have been swarmed by herds of brackets".