The Gillender Building was praised as an engineering novelty, and was quoted by some as "one of the wonders of the city". It attracted attention for a visible disproportion of height and footprint which commanded a relatively low rentable area, and was deemed economically obsolete from the start.
After thirteen years of uneventful existence, Gillender Building was sold in December 1909 for a record price of $822 per square foot of land, and was demolished in April–June 1910 to make way for the 41–story Bankers Trust tower at 14 Wall Street. The New York Times called demolition of the Gillender Building the first time when a modern skyscraper was torn down to be replaced with a taller and larger one. It briefly held the title of the tallest building ever demolished voluntarily.
In the 17th century, the site north from Wall Street was occupied by John Damen's farm; in 1685, Damen sold the land to captain John Knight, an officer of Thomas Dongan's administration. Knight resold the land to Dongan, and Dongan resold it in 1689 to Abraham de Peyster and Nicholas Bayard. Both de Peyster and Bayard served as Mayors of New York. The first known building on the site, a sugar house, was built by Samuel Bayard. In 1718, most of the present-day block was sold to a church congregation, while the corner lot, cut into narrow strips, remained in possession of the de Peysters and the Bayards. In 1773, de Peyster sold the corner lot to the Verplanck family for less than $1,500; the Verplanck mansion later housed Wall Street banks.
The second New York City Hall, erected in 1700 and torn down in 1816, stood on the site of present-day Federal Hall National Memorial and occupied the eastern side of present-day Nassau Street, which, historically, curved around the City Hall. It was straightened up after the demolition of the second City Hall, but its early track was retained in the placement of the corner buildings (including the Gillender Building but not the 14 Wall Street) which were set back from the street, providing a wider than usual sidewalk. In 1816, the corner lot was owned by Charles Gardner, who sold the property in 1817 for $11,200; it was further resold in 1835 for $47,500 and in 1849 for $55,000. Charles Frederick Briggs and Edgar Allan Poe operated the offices of the Broadway Journal on this site from 1844 until 1845. From 1849 until December 1909, the lot remained in the hands of a single family. Adjacent lots were owned by the Sampson family since 1840; in 1880, this property was developed into a seven-story Stevens Building.
In 1896, Helen L. Gillender Asinari, owner of a 6-story office building on the corner of Wall and Nassau decided to replace it with a 300-foot (91 m) tall tower, capitalizing on a tenfold increase in land value. The building was most likely named after Helen's father, millionaire tobacco merchant Eccles Gillender (1810–1877). Mrs. Gillender hurried to build the new tower prior to the anticipated enactment of new, stricter building codes, which explains the shortcomings of the Gillender Building (in fact, the regulations came into effect only in 1916). An alternative version presented by Joseph Korom attributes construction of the Gillender Building to Augustus Teophilus Gillender (born 1843), principal partner in a law firm.