Helmsley Building

Office skyscraper in Manhattan, New York

Immediately to the south are Grand Central Terminal and the MetLife Building. In addition, the building is near 50 Vanderbilt Avenue to the southwest, the Roosevelt Hotel to the west, 383 Madison Avenue to the northwest, 245 Park Avenue to the northeast, and 450 Lexington Avenue to the southeast. The Helmsley Building was developed as part of the original "Terminal City" complex above Grand Central Terminal's rail yards.

The Helmsley Building was designed by Warren & Wetmore. The design is influenced by that of the Manhattan Municipal Building, which spanned Chambers Street in Lower Manhattan, with side wings projecting to the west and east. The wings slightly resemble the "court of honor" designed by Reed and Stem, another collaborator in the Grand Central project. Inside the base are two S ramps carrying Park Avenue to the Park Avenue Viaduct. The western ramp carries southbound traffic and the eastern ramp carries northbound traffic. The building's lobby is between the two ramps, while pedestrian arcades run to the outside of either ramp; the arcades connect 45th and 46th Streets. The arcades are connected to Grand Central North, a system of passageways that lead to Grand Central, which opened in 1999. The eastern and western wings are each 15 stories tall, while a centrally positioned tower rises another 20 stories. The lowest four stories comprise the base, which include the lobbies and the viaduct ramps. The eleven stories above it comprise an office block with a floor plan shaped like an irregular "H" aligned west–east. The western wings project further than the eastern wings, and the center of the northern facade curves slightly inward.

The facade of the four story base is composed of limestone and Texas pink granite. The windows on the base contain one of four types of display window designs: the original designs installed with the rest of the building in 1929, and one of three modifications. The pedimental sculptures were carved by the Ardolino Brothers. The upper stories are faced with brick. The 15th story of the eastern facade had a sky bridge that connected to 466 Lexington Avenue until the bridge was demolished in 1982. The 16th through 35th story facades contain identical decorative elements on all sides. Like the lower stories, these are faced with brick and contain paired sash windows. Above the 28th floor are limestone keystones over the windows, as well as a cornice with brackets. The top of the Helmsley Building is a pyramid with an ornate cupola. Eight projectors, one from each corner of the octagon's base, also illuminated the roof. The lighting made the Helmsley Building into a point of interest that could be seen from several miles away. and removed in 2002.

The building has of office space. Of this, the lower 15 floors each have an area of and the upper 20 floors each cover of which went into the foundation. As a solution, girders were installed above the lower track level, and the steel frame for the building was placed upon these girders and insulated with vibration proof mats and cork tubes.

The lobby's interior is designed to evoke New York Central's "prowess". This is evidenced in the walls, which are made of marble, as well as the detailing of the bronze, where the railroad's initials are repeated many times. Another nearly identical but smaller vestibule on the southern end, near 45th Street, leads to the western walkway. The lobby contains bronze chandeliers and an elaborate cornice with brackets and friezes. with marble frames around the elevator openings, as well as bronze ornamented elevator indicators. The elevators contain elaborately decorated bronze doors painted "Chinese red", with the railroad's initials. After a fatal crash in 1902, the New York state legislature passed a law to ban all steam trains in Manhattan by 1908. New York Central's vice president William J. Wilgus proposed electrifying the line and building a new electric train terminal underground, a plan that was implemented almost in its entirety. The old Grand Central Depot was torn down in phases and replaced by the current Grand Central Terminal. Construction on Grand Central Terminal started on June 19, 1903, and the new terminal was opened on February 2, 1913. Passenger traffic on the commuter lines into Grand Central more than doubled in the years following the terminal's completion. The terminal spurred development in the surrounding area, particularly in Terminal City, a commercial and office district created above where the tracks were covered. Terminal City soon became Manhattan's most desirable commercial and office district. A 1920 New York Times article said, "With its hotels, office buildings, apartments and underground Streets it not only is a wonderful railroad terminal, but also a great civic centre." Most of these buildings were designed by Warren & Wetmore, which had also designed the terminal itself.

Following Grand Central Terminal's completion, one of the first plans for development on the Helmsley Building's current site took place in 1914, when the Winter Sports Club secured an option from New York Central to build property on the east side of Park Avenue between 45th and 46th Streets. The development of Terminal City had included the construction of the Park Avenue Viaduct, surrounding Grand Central Terminal. The first part of the viaduct had opened in 1919, carrying traffic from Park Avenue and 40th Street to Vanderbilt Avenue and 45th Street. Initially, only the western leg of the present day viaduct was open to traffic, and there was a severe bottleneck at Vanderbilt Avenue and 45th Street. As such, the city government refused to issue construction permits for buildings on Park Avenue between 45th and 46th Streets until the bottleneck was resolved. The city started negotiating with New York Central to open the eastern leg of the viaduct, although the railroad was holding out unless it was granted property on Park Avenue. At the time, New York Central had planned to build two buildings, one on either side of Park Avenue. Two years later, New York Central and the city reached an agreement to build a single building over Park Avenue, in exchange for an extension of Vanderbilt Avenue from 45th to 47th Streets, and the completion of the viaduct through the new building over Park Avenue. The project to complete the Park Avenue Viaduct proceeded after the proposal was certified by Charles L. Craig, the city controller, in 1925. The final plan for the New York Central Building above Park Avenue was not completed until February 1927. As part of the plan, the viaduct's roadways would cross over 45th Street without intersection, descending to ground level within the building. Construction of the foundation started in December 1926. At that time, New York Central opened bids for the procurement of of steel. Warren and Wetmore filed building plans in February 1927, and a contract for of steel was awarded to the McClintic Marshall Company the next month. James Stewart & Company were hired to place the foundation's piers 50 feet (15 m) deep. Because the steel beams were so large, they could not be moved through city Streets, so they were delivered by rail. The building topped out on April 5, 1928, though Chauncey Depew, the chairman of the railroad's board of directors, had died several hours before the topping out ceremony. However, the building was not considered completed until September 25, 1929, when all construction was finished. There were other railroad related tenants such as equipment manufacturer Symington Company, as well as the American Brake Shoe and Foundry Company, and the Delaware and Hudson Railway. In the first decades of the building's history, its other tenants included publisher McCall Company, paper manufacturer Eastern Manufacturing Company, and Colonial Airlines. Salvatore Maranzano, a boss for the American Mafia, had an office on the ninth floor, where he worked for the Eagle Building Corporation. On September 10, 1931, he was killed by hitmen sent by Lucky Luciano and Vito Genovese, ambitious underlings whom Maranzano had hired Vincent "Mad Dog" Coll to kill. The New York Central Building's windows were blacked out as a safety measure during World War II. Upon the New York Central's Building's renaming, the letters "C" and "T" on the facade's new york central building plaque were chiseled into "G" and "E", respectively.

New York Central had merged with the Pennsylvania Railroad in 1968 to form the Penn Central Railroad. That same year, the New York Central Building was sold to the General Tire & Rubber Company. By the next year, Penn Central trustees had signed contracts to sell the New York General Building. The proceedings were delayed for several years, as federal judge John P. Fullam refused to approve the sale of the New York General Building, while approving four of Penn Central's other sales. In December 1975, the trustees petitioned Fullam to sell the building to the New York Bank for Savings for $7 million in cash and $19 million in a 33.5 year mortgage. The sale was finalized early the next year. The major ownership stake was sold to Harry Helmsley's company Helmsley Spear Management in 1977. The facade was also extensively cleaned. The clock and other ornaments on the facade were also gilded, floodlights were activated at the top and bottom, and the letters helmsley building were installed on the facade. According to Harry Helmsley, the renaming was suggested by his wife Leona. Despite the name, the Helmsleys were only one of several stakeholders in 230 Park Avenue Associates, which owned the building. The New York City Landmarks Preservation Commission designated the Helmsley Building and its first floor interior as official city landmarks in 1987. The first floor interior designation included the lobby, seven of the eight elevator banks, and the entrance vestibules. A connection from the Grand Central North passageways to the building's pedestrian arcades was announced in 1994 and opened in 1999. Leona transferred the building's management to the Helmsley Noyes Company. Leona Helmsley maintained her offices in the Helmsley Building.

The Helmsley Building was owned by Helmsley Spear until August 1998, when it was sold to the Max Capital Management Corporation for $225 million. The terms of the sale stipulated that the building would not be renamed again. Starting in 2000, the building's arcades were shut down one at a time for renovation. The advertising boards in the arcades were removed, and the mezzanine floors in the arcades were demolished to double the ceiling height. Light shafts, TV screens, and bronze storefronts were installed as well. In 2005, the Helmsley Building was sold again to Istithmar, an investment firm owned by the royal family of Dubai, for $705 million. Two years later, it was sold to Goldman Sachs in 2007 for over $1 billion. Following a 2010 renovation, the Helmsley Building became the first building erected prior to World War II to receive a Leadership in Energy and Environmental Design certification for green buildings. RXR then spent $190 million renovating the facade and bathrooms. Many tenants left during the COVID 19 pandemic in New York City, and 20 percent of the space was vacant by 2021. A special servicer took over a $670 million Commercial mortgage backed security loan on the building in November 2023, prompting concerns that the building's owners could default on the loan.

as of 2020, tenants at the Helmsley Building include 5W Public Relations (5WPR), Cornell University, Comerica Bank, Elsevier, Encyclopædia Britannica, HSH Nordbank AG, LexisNexis, the New York Court of Appeals, Powermat, Simon Property Group, Six Flags, Stanley Hand Tools, and Voya Financial. Its tenants have been cited as a notable example of the decreased tax burden on the wealthy. Internal Revenue Service ZIP Code records in 2007 revealed that while the average tax filer in the Helmsley Building had an adjusted gross income of $1.2 million, they paid only a 14.7% effective tax rate. Meanwhile, an average New York City janitor had an AGI of $33,000 and paid an effective tax rate of 24.9%.

Early critics had mixed reviews of the building. George Shepard Chappell, writing for The New Yorker in 1928 and 1929, called it "a dramatic stop sign at the end of the thoroughfare", and described the lobby's styles as ranging "from Pullman to Paramount". Later reviews were more positive. Nathan Silver wrote in his 1967 book Lost New York: "With its outline and decoration, [the Helmsley Building] was able to indicate clearly its relationship to the height of a man." John Tauranac, in a guidebook published in 1978, said that the design was "absolutely glorious". Paul Goldberger of The New York Times wrote in 1978 that the Helmsley Building "picks up on the architectural elements of Park Avenue, but transforms them into something more exuberant". The author Dirk Stichweh said the Helmsley Building remained "a striking landmark on the New York skyline". The New York Daily News editorial team expressed disappointment that the clock was not more prominent and that there was no clock tower.