In 1885, Billy Vanderbilt was dead, just eight years after inheriting his father’s $100 million fortune. The Commodore had shocked the family by leaving almost everything to Billy, sparking…

In 1885, Billy Vanderbilt was dead, just eight years after inheriting his father’s $100 million fortune. The Commodore had shocked the family by leaving almost everything to Billy, sparking...

The Vanderbilts built their name around money, but the fortune that made them famous was barely a century old before it began to collapse. The family patriarch, Cornelius Vanderbilt, known as the Commodore, rose from a lower-class upbringing on Staten Island to dominate the shipping and railroad industries by the mid-1800s. He moved his family to Manhattan and built a home in what is now Greenwich Village, and by 1877, confined by illness, the dying Commodore sat on a fortune of more than one hundred million dollars, the equivalent of over three billion today. On his deathbed, he faced a decision that would define the family for generations: what to do with his riches.

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He gave one million dollars to establish Vanderbilt University in Nashville. Then came the shock. The will left nearly everything to a single heir, his eldest son, William Henry Vanderbilt, known as Billy. The other son and nine daughters were cut out entirely.

The family was furious and suspicious. Three of Billy’s siblings took him to court, accusing him of hiring a spiritualist to dupe their father into handing over the entire fortune. Billy avoided the scandal of a public trial by settling with his brothers and sisters, though the terms were far from generous. Billy did not live long enough to enjoy his inheritance.

In 1885, just eight years after his father’s death, he died of a stroke. But in that short window he had doubled the family fortune. Money did not bring him happiness. He said it made him anxious, blamed his wealth for his poor health, and envied his poorer neighbors.

Upon his death, most of the fortune passed to his two eldest sons. Cornelius Vanderbilt II gave so much away that he failed to grow the family wealth, while his brother William Kissam Vanderbilt cared far more for horses than for business. William Kissam Vanderbilt married Alva Erskine Smith in 1875. Alva had extravagant tastes.

She demanded yachts and collected mansions, eventually boasting nine residences. But possessions were not enough. New York high society refused to accept the Vanderbilts because their money was new money, not inherited through generations. Alva tried to buy her way in through architecture, spending three years and three million dollars building a suitable home.

She was a harsh mother to her daughter Consuelo, striking her with a riding crop and forcing her to wear a steel rod to correct her posture. What Alva truly wanted was a royal title. She arranged for Consuelo to marry Charles Spencer-Churchill, the Duke of Marlborough. Neither bride nor groom wanted the union, but both families had reasons to accept.

Alva gained her connection to royalty, and the Duke gained access to the Vanderbilt fortune to save his estate from financial collapse. The marriage lasted twenty-six years. Just before the wedding, Alva announced she wanted a divorce from William, an unthinkable move in high society at the time. She claimed he had cheated, though some believed he had hired a woman to pretend to be his mistress in order to escape the marriage.

William remarried, moved to France, and devoted himself to his beloved horses. He famously said that inherited wealth was a handicap to happiness, leaving him with nothing to hope for or strive toward. The next generation continued the pattern. George Washington Vanderbilt II decided he wanted a truly enormous house.

He bought 125,000 acres in North Carolina and hired an architect to build what remains the largest private home in America, a 250-room estate covering more than 175,000 square feet. The Biltmore mansion drained the family fortune, and maintaining it was almost as costly as building it. George and his wife Edith were overwhelmed by the expense, and in 1914 George died during a routine appendectomy. Edith inherited the monumental house and all its financial burdens.

In 1930, the family made an unthinkable concession: the estate was opened to the public so that anyone could see how the Vanderbilts had lived. In Newport, a similar story unfolded. The seventy-room Breakers mansion, built in 1895 for Cornelius Vanderbilt II, was eventually leased to a preservation society for one dollar a year. Reginald Claypool Vanderbilt, known for gambling away the family fortune and for his many affairs, died young from drinking.

His brother Cornelius Vanderbilt III, called Neily, spent lavishly just to keep up appearances in society. He once boasted that he was the first Vanderbilt heir to shrink the family fortune. When his father objected to his marriage to Grace Wilson in 1896, the couple eloped, and his parents disinherited him. When the inheritance finally came, Neily received half a million dollars while his brother Alfred received nearly seventy million.

Alfred Gwynne Vanderbilt seemed to have a better head for responsibility, except in marriage. Seven years into his marriage to Ellen Tuck French, she moved out, allegedly because of his affair. But in 1915, during a business trip to Liverpool aboard the RMS Lusitania, a German submarine torpedoed the ship off the coast of Ireland. As the vessel sank, Alfred gave his life vest to a terrified woman holding her baby.

More than a thousand people died that day, and Alfred was among them. By the 1930s, the Great Depression hit the family hard. Reggie’s widow, Gloria Morgan, and their infant daughter Gloria were left with almost nothing. Gloria Morgan had not been born a Vanderbilt, so she could not claim the family fortune; but her eighteen-month-old daughter, the Commodore’s great-great-great-granddaughter, stood to inherit a colossal sum at age twenty-one.

Reggie’s sister Gertrude wanted custody of the child, and the ensuing trial became a media sensation. Witnesses painted a damning picture of Gloria Morgan. Her nurse described a filthy home infested with rodents and claimed she was cruel to little Gloria. A maid scandalously testified that she had seen Morgan in bed with another woman, and the courtroom had to be cleared.

Most stunning of all, the child herself said she was afraid of her mother. Gloria’s testimony had been coached by her aunt Gertrude, and the plan worked. The aunt won custody. The young Gloria Vanderbilt had little contact with her mother after the trial, and her aunt was not a warm substitute.

She turned to her nanny as a mother figure. She later pursued acting, appearing on Broadway and in live and recorded television dramas. At fifteen she began modeling, and she proved to be a skilled painter whose work appeared on a line of scarves. An offer came to place her signature and a swan logo on the pocket of a pair of blue jeans, at a time when designer denim barely existed.

She and designer Mohan Murjani made the jeans very tight, and they became a huge success. She married director Sidney Lumet, then Wyatt Emory Cooper, with whom she had two sons. That marriage lasted fifteen years until Cooper died on the operating table at age fifty. In 1988, her twenty-three-year-old son Carter jumped from the family’s fourteenth-floor penthouse apartment in New York.

Her other son, Anderson Cooper, took a different path. Early in life his mother assured him there would be no trust fund. He rose to prominence without using the Vanderbilt name, proof that the family fortune had run its course. The reasons for the collapse were clear by the time the family gathered for a reunion in 1973.

Looking around the room, they realized that not one of them was a millionaire. The fortune had lasted roughly a century. The Commodore had made his descendants’ lives easy but had not taught them how to hold on to wealth. Fellow patriarch John Jacob Astor had taken a different approach, setting up trusts that required wealth to be split between children and grandchildren so that future generations learned to preserve it.

The Vanderbilts, meanwhile, spent enormous sums on mansions that were left empty most of the year and could not be passed down. Their New York properties, built for extravagant prices, were gone by the 1940s, reduced to rubble. Even in death the family remained dramatic: the Vanderbilt mausoleum on Staten Island, designed by architect Richard Morris Hunt and inspired by a French abbey, stands as a New York City landmark.

The family’s name once meant unimaginable wealth, but in the end, it became a reminder that fortunes are only lasting if someone is willing to protect them.