In the winter of 1890, Caroline Webster Schermerhorn Astor, the undisputed queen of New York society, stood at the window of her mansion on Fifth Avenue and looked out at the most beautiful view money could buy. To the south stretched the avenue she had helped make fashionable. To the north lay the homes of families who had spent decades trying to win her approval. Before the decade was out, that view would be destroyed, and the most expensive family feud in American history would build one of the world’s most famous hotels.
Caroline Astor was born in 1830 into the Schermerhorn family, old Dutch money that traced back to colonial New York. In 1853, at age twenty-three, she married William Backhouse Astor Jr. , grandson of John Jacob Astor, the fur trader and real estate speculator who had died in 1848 as the wealthiest man in America, worth an estimated twenty million dollars. The Astor fortune sat primarily in Manhattan real estate.
John Jacob had bought up huge tracts of undeveloped land, betting the city would expand northward. He was right, and the family collected rent from thousands of properties. By the time Caroline married into the family, the Astors were worth an estimated fifty million dollars. They were possibly the richest family in America, but wealth alone did not guarantee social position.
The Astors were still considered new money by the Knickerbocker families who had been in New York since the 1600s. Caroline understood that if the Astor name was to maintain preeminence, it needed to dominate socially, not just economically. Over three decades, she systematically established herself as the arbiter of New York society. She created the list of acceptable families, the famous 400, supposedly the number of people who could fit in her ballroom, but really the number she deemed worthy.
If Caroline Astor invited you to her annual ball, you were somebody. If she did not, you were not. She partnered with Ward McAllister, a social climber who understood the mechanics of exclusivity. Together they created elaborate rules for who could be received in polite society.
Caroline became known simply as the Mrs. Astor, as if no other woman with that surname mattered. Her mansion at 350 Fifth Avenue, built in 1859, became the center of New York society. By 1890, Caroline was sixty, and her control was beginning to slip, not because she was less formidable, but because the world was changing.
New money was flooding into New York, industrialists who did not care about old social rules. More threateningly, the Astor family itself was fracturing. The male heir who would inherit the bulk of the fortune was her nephew, William Waldorf Astor, son of her husband’s brother. Born in 1848, William Waldorf was everything Caroline was not: intellectual, cultured, educated at Columbia and Heidelberg, a writer of novels and poetry.
He was also resentful, deeply resentful of Caroline. He believed that as the eldest male Astor of his generation, he should be recognized as head of the family. Caroline disagreed. She had spent thirty years establishing herself as the Mrs.
Astor and had no intention of ceding that position. The conflict came to a head in 1890 when William Waldorf’s wife, Mary Paul Astor, began calling herself Mrs. Astor in social correspondence. In the rigid world of Gilded Age society, it was a declaration of war.
Caroline responded swiftly. She made it clear through her social network that Mary Waldorf Astor was not the Mrs. Astor, that anyone who accepted Mary’s claim would not be received by Caroline. Given that Caroline controlled access to New York society, this was an effective threat.
People chose Caroline. William Waldorf was furious. He decided to do something dramatic, something that would force Caroline to acknowledge his power or destroy her peace. In late 1890, he purchased the property at Thirty-third Street and Fifth Avenue, directly adjacent to Caroline’s mansion, and announced he was going to build a hotel.
Not just any hotel, but the largest, most luxurious hotel New York had ever seen, thirteen stories tall, filling the entire block, with a kitchen that could serve a thousand guests simultaneously. It was architectural warfare, and everyone understood exactly what he was doing. In 1890s New York, hotels were not respectable. They were commercial establishments where traveling salesmen and people of uncertain background mingled.
Having a hotel in your neighborhood suggested your area was declining. Having one directly adjacent to your mansion was an announcement that your position was under siege. Construction of the Waldorf Hotel began in spring 1891. The architect was Henry Janeway Hardenbergh, who had already established his reputation with the Dakota apartment building.
The Waldorf would be thirteen stories tall. Caroline’s mansion was four. It would be built in the German Renaissance style, elaborate and ornate, covered in carved limestone. The entrance would be on Thirty-third Street, directly beside Caroline’s property line, meaning hundreds of guests would arrive and depart every day next to her home.
The hotel would have a ballroom that could hold twelve hundred people, three hundred more than Caroline’s famous ballroom. Construction proceeded through 1891 and 1892, and with each month the building rose higher, casting more shadow over Caroline’s property. The noise was constant. In June 1892, Caroline gave an unusual interview to the New York Times.
“My nephew has chosen to build what amounts to a glorified tavern next to my home,” she told the reporter. The phrase became famous. By calling the hotel a tavern, she reduced it to a common drinking establishment. William Waldorf did not dignify her insult with a direct reply.
He simply announced more extravagant details about the hotel. The Waldorf Hotel opened on March 14, 1893. Fifteen hundred guests attended the opening night gala. Rooms cost between three and five dollars per night and were fully booked within days.
The restaurant became immediately fashionable. The hotel was a cultural phenomenon, and it was right next door to Caroline’s mansion. Caroline had not been passive during the construction. She had been planning her response.
She was talking to her son, John Jacob Astor IV, born in 1864, her only surviving son, deeply loyal to his mother. Caroline owned the mansion at 350 Fifth Avenue, but John Jacob owned the land immediately to the north, at Thirty-fourth Street and Fifth Avenue. Caroline’s plan was magnificent in its pettiness. If she sold her mansion and John Jacob developed his land, they could build a hotel even larger than the Waldorf, directly adjacent to it on the other side.
But there was more. Caroline proposed that their hotel would not just be adjacent to the Waldorf, it would be designed to connect to it. If William Waldorf agreed, the two hotels could be joined, creating the largest hotel in the world. If he refused, their hotel would be a direct competitor.
Either way, Caroline won. Construction plans were drawn up in secret through the summer of 1893. In September, Caroline made her announcement at her annual ball. She waited until all four hundred guests were seated, then stood.
“This will be the last ball held in this location,” she said. “My son, John Jacob, and I will be demolishing both our mansions and building a hotel that will make the Waldorf look like, well, the glorified tavern it is. ” The room erupted. “The Astoria Hotel,” she said.
The name was deliberate. It would be seventeen stories tall, have five hundred rooms, and open in 1897. She added that she had sent word to her nephew that should he wish to discuss connecting their properties, she would be amenable to negotiation. William Waldorf Astor was in England when he received the news.
He had moved there in 1891, ostensibly because he preferred European culture, but really because he had lost the social war with Caroline. His first instinct was to refuse any cooperation. His business advisers pointed out the reality. Caroline had the social connections to make the Astoria successful.
If the Astoria opened in competition with the Waldorf, it would split the luxury hotel market, and both properties might suffer. If the hotels were connected and marketed as a single entity, they would have an overwhelming competitive advantage. After three months of negotiation through lawyers, William Waldorf agreed to the merger. The Waldorf and Astoria would be connected by a corridor.
The agreement included a provision that became famous: either family could sever the connection by closing a set of heavy steel doors built into the corridor. Construction of the Astoria began in 1895, with Caroline overseeing every detail. She hired Henry Janeway Hardenbergh, the same architect who had designed the Waldorf, a deliberate choice. She wanted someone who understood the Waldorf intimately.
The Astoria would be seventeen stories, four taller than the Waldorf, with five hundred rooms. The main ballroom would hold fifteen hundred people. The dining room would double as an art gallery, displaying Caroline’s personal collection of paintings. The marble would come from Carrara, the quarries that had provided stone for Michelangelo.
The budget exceeded three million dollars, nearly twice what William Waldorf had spent. Caroline’s strategy went beyond architectural one-upmanship. She let it be known through her social network that the Astoria would be her hotel, that she would be maintaining an apartment there, that she would be receiving guests there. Being invited to the Astoria would be equivalent to being invited to one of her private balls.
William Waldorf, watching from England, understood what she was doing. The combined hotel was already generating enormous interest. Reservations were being made months in advance. Separating the properties would be financial suicide.
He was trapped. The Astoria Hotel opened on November 1, 1897, with a gala that made the Waldorf’s opening look modest by comparison. Twenty-five hundred guests attended, the largest social gathering in New York history. Caroline Astor received guests in the grand ballroom wearing a diamond tiara and a necklace that had belonged to Marie Antoinette.
She was sixty-seven years old, still formidable, still commanding. The press coverage was ecstatic. The Waldorf-Astoria, with eighteen hundred rooms, was the largest hotel on Earth. The hotel became immediately profitable.
Within two years, the combined property was generating over two million dollars annually in revenue, roughly sixty million today. Caroline Astor won her feud. She maintained an apartment on the fifth floor of the Astoria, and from there she continued to rule society for another decade. When she died in 1908, her funeral was held in the Astoria’s ballroom.
Three thousand people attended. William Waldorf Astor did not attend. He remained in England, where he had purchased Hever Castle. He would eventually be made a viscount, becoming the first American to sit in the House of Lords.
But when people thought of the Astors, they meant Caroline’s branch of the family. The Waldorf-Astoria operated at its original Fifth Avenue location until 1929, thirty-two years during which it defined luxury hospitality worldwide. Room service was standardized there. Oscar Tschirky developed the concept of a hotel having its own signature cuisine.
The Waldorf salad was created there. The idea that a hotel should have multiple restaurants, that a hotel ballroom should be a venue for society events, all became standard because of the Waldorf-Astoria. In 1929, the property was sold to the Empire State Building Corporation. The original Waldorf and Astoria were demolished to make way for the Empire State Building.
A new Waldorf-Astoria was built on Park Avenue, forty-seven stories with twenty-one hundred rooms, opening on October 1, 1931, in the depths of the Great Depression. It succeeded anyway, assisted by the fame of its name. Every president from Herbert Hoover to Barack Obama stayed there when visiting New York. In 2014, the Waldorf-Astoria was sold to a Chinese insurance company for $1.
95 billion, the most expensive hotel sale in history at that time. The building that Caroline and William Waldorf’s feud had inspired came full circle. The monument to their pettiness became one of the most valuable properties on Earth. Would it have been built without their feud?
Probably not. William Waldorf might never have conceived of building a hotel if not for his resentment of Caroline. Caroline certainly would never have demolished her mansion to build the Astoria if William Waldorf had not provoked her. The Waldorf-Astoria exists because two wealthy people could not stand each other and had the resources to express that hatred through architecture.
The spite was temporary, the architecture permanent. They were small people with enormous resources, and despite themselves, they created something larger than their pettiness.