“Before the age of the skyscraper, buildings like this were the monuments of the city,” Anthony W. Robbins, the author of “Grand Central Terminal: 100 Years of a New York Landmark,” said during a recent tour of the station. “When you can see the sides of the station, it really reads as a monument.”

Grand Central’s architects, Warren & Wetmore, planned the buildings that would surround their greatest work, demanding masonry bases that would match the station. In so doing, though, they largely obscured Grand Central, and the station became a victim of its own success, walled off by ever-growing towers.

While the five buildings demolished to make space for One Vanderbilt were among the longest standing in Terminal City, they were some of the least distinguished. One, known as the Vanderbilt Avenue Building, or 51 East 42nd Street, was a six-story office complex that opened a year before the terminal and had another dozen floors added in the 1920s. Designed by Warren & Wetmore, its distinguishing feature in recent times was the Modell’s sporting goods store on the first two floors, its memorabilia-filled windows among the first things people saw when they walked out of Grand Central.

Other properties included the Liggett Building, designed by Carrère & Hastings (renowned for designing the main branch of the New York Public Library on Fifth Avenue) and opened in 1922, on the corner of Madison Avenue and 42nd Street, and the Prudence Bond & Mortgage Building, on 43rd Street and Madison Avenue, which opened the next year. Gov. Alfred E. Smith had his office in the Prudence building, from which he ran his campaigns and, upon leaving Albany, oversaw the construction of a different landmark, the Empire State Building. Rounding out the group of demolished structures were two smaller office buildings wedged on West 43rd Street, which were most recently home to an Irish pub and a T.G.I. Friday’s.

When SL Green’s plans for the block emerged, there was little outcry from preservationists, who knew change was coming. The administration of the previous mayor, Michael R. Bloomberg, had pushed to rezone the area to allow for taller buildings and make it a magnet for business. And there was little ambivalence about the demolition of the buildings, which were attractive but unimportant.

Image A rendering of One Vanderbilt, left, which is scheduled to be finished in 2020. Credit... KPF

“No one seriously thought the Modell’s building was particularly significant in the broader scope of the Terminal City development,” said Simeon Bankoff, executive director of the Historic Districts Council, an advocacy group.