The dark mass of 53-story One Liberty Plaza was an unusual departure from the glass curtain-wall typical of International Style office buildings. One Liberty Plaza's thick columns and horizontal steel spandrels, which have the appearance of massive I-beams, give the building enhanced strength and were appropriate for the tower’s original tenant, the U.S. Steel Company. The exterior walls, which are an integral element of the building's structure, showcase an advanced use of steel in high-rise construction. This structural system frees the building of most interior columns allowing for a more open and readily adaptable floor plan. One Liberty Plaza occupies the site of the Singer Building (once the world's tallest) and City Investing Company Building (once the world's largest) both built-in 1907 and demolished in 1969. The Singer Sewing Machine Company initially commissioned Ernest Flagg to design a 35-story tower, but soon decided to nearly double that height to 600 feet. Completed in 1908, just twenty months after the foundations were set, the Beaux-Arts style tower clad in red brick and bluestone stretched to 612 feet, besting 15 Park Row by more than 200 feet. However, the Singer Building held the title for only a year before it was surpassed by the Metropolitan Life Tower at Madison Square. The tower's demolition sparked a little protest at the time. Major losses throughout the 1960s -- Penn Station being the most prominent -- galvanized public concern regarding the preservation of landmark-quality buildings. Architectural critic Ada Louise Huxtable described the Singer Building's last hours: "Piranesi anyone? The master never produced a more impressive ruin than the Singer Building under demolition. Curious New Yorkers who risk a piece of Pavonazza marble on the head by looking beyond the boarding that surrounds the tower will find a scene of rich, surrealist desolation. Domed vaults supported by bronze trimmed marble columns await the sledgehammer in the half-light and plaster dust. The distinctive tower, a triumph of 'modern' steel construction that added its Beaux-Arts silhouette to the picturesque bouquet of early skyscraper spires, will probably be replaced by one more 'flat-top,' diminishing the character of the downtown skyline."
Erected simultaneously with the Singer Building was the City Investing Building, a speculative office block that contained more rentable space than any other in the city at the time of its completion in 1908. Francis Kimball, the architect of many other early skyscrapers, designed it. The building occupied an awkward and long site with narrow frontages on Broadway and Church Street. Liberty Park occupies the full block directly to the south. The developers of One Liberty Plaza in exchange for additional floors created it under an incentive available under the 1961 Zoning Law.
On the block that is now the open plaza to the south of the skyscraper once stood the Washington Life Building, an early skyscraper of 1898 by Cyrus L. W. Eidlitz.
