The fortune of Cornelius Vanderbilt, the richest American of his era, was worth roughly $100 million when he died in 1877, a sum often compared to several billion in today’s money. Within about 50 years, nearly all of it was gone, not stolen or lost in a single market crash, but spent down quietly and in plain sight. The most visible symbol of that wealth was once Fifth Avenue in New York. For roughly 40 years, from the 1880s into the 1920s, the blocks along Central Park held the largest concentration of private wealth in American history.
Single families lived in marble palaces built on the scale of public buildings, in an era when being a millionaire placed you beyond the reach of almost everyone alive. The Astors were there. Several branches of the Vanderbilts lived within sight of one another. Andrew Carnegie built near the top of the avenue.
Henry Clay Frick built lower down. A copper millionaire named William Clark put up a house with more than a hundred rooms. The country was founded against the idea of inherited aristocracy. It had no dukes or titled family seats.
Yet within a single generation, it grew one anyway, on one avenue in stone and marble for everyone to see. Today, almost none of those families remain there, and the houses are gone. The money, however, did not simply vanish. It changed hands, changed shape, and changed address until it became almost impossible to recognize as the same thing.
The story of that avenue begins with a social barrier that had nothing to do with cash. The old New York families, wealthy since before the country had a flag, watched the city fill with railroad and oil fortunes and set out to draw a line the newcomers could not cross. The person who policed that line was Caroline Astor. Her instrument was the invitation.
If Caroline Astor called on your family, you existed. If she did not, no amount of millions could make you matter. Her winter ball in her own ballroom was the one room in the city that settled who belonged. Being left off her list could shape which clubs admitted your husband and whether your daughter married well.
A social advisor named Ward McAllister appointed himself keeper of the rules and gave the arrangement its famous number. There were, he announced, only 400 people in New York who genuinely mattered. The rest were not at ease in a ballroom. The number reportedly came from the capacity of Caroline Astor’s own ballroom.
The Vanderbilts, whose railroad fortune was enormous, spent years on the wrong side of that line. Then Alva Vanderbilt, who had married into the family, built a Fifth Avenue house larger and louder than anything the older families owned. In 1883, she announced a costume ball that all of New York wanted to attend, and let it be known that no invitation would go to any family she had not formally received. Caroline Astor’s own daughter was desperate to attend.
To secure her daughter’s place, Caroline Astor was forced to do the thing she had refused to do for years: she called on Alva Vanderbilt. The barrier cracked loudly, and the whole city heard it. There is a cruel footnote. Ward McAllister, the man who had named the 400, grew too fond of attention.
He gave interviews and published a memoir. Polite society decided he had embarrassed them and dropped him. He died a few years later, dining alone at his club. Caroline Astor did not attend his funeral.
While these families fought over who could enter a ballroom, a larger force was taking shape in Washington. It would arrive quietly, as a few lines in the tax code, and it would not care how old a fortune was. For most of the era in which these fortunes were built, the federal government could not touch a dollar of them. There was no income tax.
That world ended in 1913, when a new amendment to the Constitution gave Congress the power to tax income directly. Within months, the first modern income tax became law. The top rate was 7 percent and reached only the very rich. Then came the First World War.
To pay for it, the government raised the top rate again and again. By 1918, it had reached 77 percent. In five years, a system that took almost nothing had begun claiming the majority of the largest incomes in the country. The rates came down after the war, but they never came down to nothing.
A federal estate tax arrived in 1916. For the first time, when the head of one of these families died, the government took a share of everything he left behind. A gift tax followed to stop families from simply handing everything over early. The machinery for passing a fortune down, whole and intact, had quietly been taken apart.
American wealth reached its peak around 1929, and the crash that followed wiped out a great deal of it. By the early 1930s, the reported value of the country’s largest estates had fallen by close to a third. A government starved for revenue pushed the top rates higher still, and a public that had once admired these fortunes began voting for the men who promised to tax them. The houses themselves added to the weight.
A Fifth Avenue palace was punishing to keep. It took a staff of dozens just to keep the doors open, and the heating and repair bills never let up. Taxes alone did not empty these houses. What finished the job, family after family, was that heirs spent as though nothing had changed.
No family spent more freely or fell further than the one that had begun with the largest fortune of all. In 1973, about 120 descendants of Cornelius Vanderbilt gathered at Vanderbilt University for a family reunion. By one often-repeated account, not a single person in the room was a millionaire. It began with the Commodore’s will.
When he died in 1877, he left almost the entire fortune to a single son, William Henry, and only modest sums to everyone else. He attached no conditions, no trust, no rules about spending or saving. He handed over the largest fortune in America and trusted his family to hold on to it. William Henry did more than hold on.
In about eight years, he roughly doubled it, building what was by then the largest fortune in the world. Then he split it among his children. A fortune divided is a fortune that can be spent in pieces. The third generation had a different relationship with the money.
They had not built it. Most had never spent a day at the business that produced it. What they knew how to do was spend, on a scale the country had never seen. They put up palaces in the city and even bigger ones in Newport, summer houses so enormous that calling them cottages became a private joke.
No one showed where this led more clearly than Reginald Vanderbilt, the Commodore’s great-grandson. By one account, the night he turned 21, he came into an inheritance of around $15 million. He lost $70,000 at the gambling table before sunrise. He spent the rest of his short life at the track and the card table.
Doctors warned him at 42 that drinking would kill him. It did, three years later, in 1925, deep in debt, with almost nothing left of what he had been given. The railroads, the thing that made the money, were also dying. By the 1930s, they were losing ground to the automobile and to buses and planes.
The Vanderbilts began selling off their stake. In time, the New York Central passed out of the family’s hands, and not long after, the railroad itself collapsed into bankruptcy. The picture is almost mechanical. The fortune was divided until no heir held real power over it.
They spent faster than anyone could earn. At every death, the tax took its share. And underneath everything, the business itself was dying. The Vanderbilts were not robbed.
No one had to do anything wrong. They only had to relax. Not all of the family’s money was lost at the card table. Some of it left in a far more deliberate way.
It crossed the Atlantic as a bride. For a few decades, turning new American money into an old European title became something close to an industry. By the late 1800s, much of the British aristocracy was in trouble. They held the titles and the ancient houses, but a long farming slump had drained the cash that kept those houses standing.
American families had vast fortunes and no pedigree, and a closed society at home that would never fully let them in. A trade took shape: American money for European rank. By one count, between 1870 and the start of the First World War, more than 400 American heiresses married into the titled families of Europe. The most famous was Consuelo Vanderbilt.
Her mother, Alva, pushed her in 1895 into marrying the ninth Duke of Marlborough, a man Consuelo barely knew and did not love. By her own account, she wept behind her veil on the way to the altar. The Duke needed the marriage because his family seat, Blenheim Palace, was falling apart and he could not afford to keep it standing. The Vanderbilt dowry, reportedly worth a few million dollars in railroad stock, fixed that.
The marriage ended in divorce, but Blenheim still stands, saved by Vanderbilt money. The bloodlines ran further. An American heiress named Jenny Jerome had married a British lord, Randolph Churchill. Their son was named Winston.
Through another of these marriages, an American heiress turned out to be a great-grandmother of the woman the world later knew as Princess Diana. Plain disgust was another way the money left. William Waldorf Astor, heir to the enormous Astor real estate fortune, decided that America was, as he put it, no longer a fit place for a gentleman. He moved to England, became a British subject, bought a crumbling castle called Hever, poured a fortune into rebuilding it, and was eventually made a viscount.
In every other direction, the money simply disappeared. Here it did not. Blenheim Palace and Hever Castle are still standing, and much of the money that built them remains in the stone. One family watched all of this happen and drew the opposite conclusion.
They decided their fortune would never be split among careless heirs and never allowed to drift away. So they locked it down, not in a vault, but in a structure built out of law itself. That family was the Rockefellers. John D.
Rockefeller built, through Standard Oil, what most historians consider the largest fortune in American history, larger even than the one the Commodore left behind. Rockefeller was careful with money to the point of obsession. As a young clerk, he kept a small notebook recording every cent he earned and spent. He made his own children keep account books too.
While the Vanderbilts were putting up marble palaces, the Rockefellers lived in a comparatively plain brownstone just off Fifth Avenue. Over time, the family did something the others never had. They locked the fortune inside trusts. Money placed in a trust does not belong outright to any single heir.
It is held by professional trustees under rules the heirs cannot easily break. The family built their first major trust in the 1930s and a larger one in the 1950s. The instruction was simple: live on what the fortune earns, never touch the fortune itself. Rockefeller gave away enormous sums to universities, medical research, and a foundation that still carries the name.
His son built Rockefeller Center. Instead of turning the money into parties and palaces that would not outlive them, the family turned it into institutions that would. Giving much of it away was, in the end, part of how they kept the rest. It worked.
More than a century later, the Rockefeller name is still wealthy. By most estimates, the family has held a fortune together across six or seven generations, shared among a couple of hundred descendants. No single one of them is as rich as the founder was, but as a family, they did the one thing almost no one else in this story managed. They kept it.
Meanwhile, the mansions came down. William Clark’s Fifth Avenue house had 121 rooms and cost about $7 million to build, worth well over $100 million today. It was finished in 1911 and pulled down in 1927. A house built to stand for centuries was gone in 16 years.
All up and down Fifth Avenue through the 1920s and into the 1930s, the great houses came down. A Vanderbilt palace at the edge of Central Park was demolished, and the department store Bergdorf Goodman rose on the spot. Caroline Astor’s mansion was torn down, and a synagogue rose in its place. Why did they let it happen?
Taxes and ruinous upkeep had turned against them. On top of that, the land had become worth more than the houses standing on it. A mansion site could hold an apartment tower full of paying tenants. Kept as a single-family home, it was simply a way to lose money.
So the families sold, and the wreckers came. Pieces of the houses survived. The bronze gates of the Vanderbilt mansion still stand in Central Park at the entrance to the Conservatory Garden, passed every day by people who do not know they once guarded a vast palace. A fireplace from the same house was given to the Metropolitan Museum.
The fortunes that built Fifth Avenue had been reduced to spare parts in a public park. For a long time, tearing the mansions down did not feel like a loss. To many New Yorkers, these houses were embarrassments, the bloated monuments of an age the country was glad to be rid of. The demolition felt like progress.
Then, in the early 1960s, the destruction reached something people could not bear to lose: the old Pennsylvania Station, a soaring public monument, was knocked down to make room for an arena and an office block. The loss shocked the city. On Fifth Avenue, the wreckers came for the Brokaw mansion, a heavy stone house at 79th Street. This time there was an outcry.
A newspaper called its destruction an act of vandalism against the city’s own history. It was too late to save the Brokaw house, but not too late to save the rest. In 1965, New York passed its first real law to protect historic buildings. It came too late for Millionaires’ Row, almost all of which was already gone.
But it froze what little remained. The handful of survivors had to become something else, because no private family could afford to live in a Gilded Age mansion anymore. They became museums. Henry Clay Frick had planned for exactly this, intending his mansion to open to the public as a gallery for his art collection.
He died in 1919, and in 1935 his house did just that. You can still walk through the rooms today. Andrew Carnegie’s mansion uptown became a design museum. On most of the avenue, something new was going up in the place of the mansions: the apartment building.
It started in 1916, when the first of a new kind of apartment house went up on Upper Fifth Avenue on a lot where a private mansion had stood. At first, the old families were horrified. Living stacked on top of strangers was beneath them. But the apartments being built were mansions turned on their end.
In the 1920s, a designer named Rosario Candela became the architect of choice. His buildings, faced in pale limestone, rose along Fifth Avenue, and the apartments inside were enormous: 15 rooms, 20 rooms, servants’ quarters, private libraries, and ballrooms set high above the street. One building at 960 Fifth Avenue went up on the exact lot where Clark’s 100-room palace had been torn down. The palace was gone, but the address simply climbed back into the sky.
There was a logic to it. A single family could no longer carry the cost of a palace. But a dozen wealthy families, each buying a single floor, could manage it together. The cooperative was the old mansion split among many owners.
The old exclusivity quietly reasserted itself. You could not simply buy your way into one of these buildings, no matter how rich you were. Each one was run as a cooperative, governed by a board of the people who already lived there, and that board decided who was allowed to buy. They could turn you down for any reason or for none at all.
A century after Caroline Astor decided who counted by sending or withholding an invitation, the same power lived on, moved from her ballroom to a board meeting. Perhaps the best-known resident of this vertical Fifth Avenue was Jacqueline Kennedy Onassis. After the White House, she came home to New York and bought an apartment high up in one of the Candela buildings, looking out over Central Park, and lived there quietly for the rest of her life. The horizontal palace had become the vertical apartment.
The ballroom became the boardroom. A few blocks south, a different kind of money was rising into the sky. From the south edge of Central Park, the new towers are impossibly tall and impossibly thin, needles of glass. Even after dark, a great many windows have no lights on at all.
Nobody is home. Often, nobody ever is. This is Billionaires’ Row, running mostly along 57th Street and the southern rim of the park, a few blocks from where the Vanderbilt palaces once stood. It is the same money in the same corner of the same city, simply rearranged.
The buildings are called supertalls. Central Park Tower is among the tallest residential buildings ever raised. They are engineered to be needle-thin so that as many apartments as possible can sit far above the rooftops. The higher the floor, the better the view of the park, and the higher the price.
The numbers are hard to take in. In 2019, hedge fund billionaire Ken Griffin bought a penthouse at 220 Central Park South for about $238 million. Years later, it is still the most expensive home ever sold in the United States. His office explained it was simply a place for him to stay when he was in town.
That is the pattern all along the row. The apartments are bought by hedge fund and technology fortunes and by wealthy families from overseas. Many are purchased not in a person’s name, but through anonymous companies. Many are not first homes.
They are the fourth or the fifth, visited for a few weeks a year, and then left dark. People in real estate have a name for what these towers really are: safe deposit boxes in the sky. A Gilded Age mansion was alive. A family lived there, with servants filling the back stairs, in a house used every single day.
These towers hold none of that. A unit can change hands for the price of a hospital and then stay dark and silent for years. The wealth is real. The home is a fiction.
This is the deepest difference between the old money and the new. The families who built Fifth Avenue wanted to be seen. The whole point of a marble palace with your name carved over the door was that the city would look at it and know exactly who you were. The new money wants the reverse.
It pays enormous sums to own without being named. The Gilded Age turned money into a monument. Today, money turns itself into a hiding place. There is an old saying about money that explains almost everything: from shirt sleeves to shirt sleeves in three generations.
The first generation builds the fortune working in its shirt sleeves. By the third, having known nothing but money, the family has lost it and ended up back where it started. One widely cited study of wealthy families found that around seven in ten lose their wealth by the second generation, and about nine in ten by the third. The Vanderbilts were not unusual.
They were the rule, written very large. The regular Vanderbilt fortune is gone. The American Astors faded, their title living on quietly in England. Only the Rockefellers, who treated money as something to guard rather than enjoy, are still standing as a fortune.
One family out of all of them. All of this has a face. Anderson Cooper, the journalist who has read America’s evening news for more than 20 years, is a great-great-great-grandson of Cornelius Vanderbilt. He did not grow up on that money.
By the time he came along, it was effectively gone. His mother, Gloria Vanderbilt, became a celebrated designer in her own right. When she died in 2019, she left her son relatively little, and he did not expect more. Cooper has built his career himself and has said plainly that he never wanted the family fortune.
He has called the idea of inheriting that kind of money a curse. The family that built palaces the size of city blocks produced as its best-known living member a man who earns his own salary. Cornelius Vanderbilt had clawed his way up from a single boat in New York Harbor to the top of an entire economy. He had little faith that his heirs understood how fragile money really is.
He was right to worry. What he could never have pictured was how fast and how completely the thing he built would come undone. The lesson is quieter than that wealth is bad. It is that nothing holds, not even a fortune that size, and not even a house built to outlast everyone who lived in it.
The money that built Fifth Avenue is still in the city, changed beyond recognition. It is in a trust no heir can touch, in a museum you can wander through, in an English castle, in a dark apartment 90 floors above the street. It went everywhere and became everything except the one thing its owners most wanted, which was to stay.