Barbara Hutton was born in November 1912 into the Woolworth fortune, a retail empire built on five-and-ten-cent merchandise. Her grandfather, Frank Winfield Woolworth, had built the tallest skyscraper on Earth and paid for it in cash. Her mother, Edna, died at the Hotel Plaza when Barbara was four, officially from a bacterial infection, though rumors persisted that the child herself found the body.
Her father, Franklin Hutton, co-founder of E. F. Hutton & Company, showed little interest in his daughter and eventually left his entire estate to his second wife.
By the time Barbara turned 21, her inheritance had grown to $42 million, roughly $900 million in today's currency. Franklin had pulled his money from the stock market weeks before the 1929 crash, preserving and growing the fortune while the rest of the country stood in breadlines. The press crowned her the richest girl in America and gave her a nickname that would follow her to the grave: poor little rich girl.
Her debutante ball at the Ritz-Carlton in 1930 cost $60,000, featured three orchestras, and was attended by over 1,000 guests including Astors and Rockefellers. It took place barely a year after the Wall Street crash, and columnist Walter Winchell branded her society's most outrageous child. Barbara herself later admitted the party was a terrible slap in everybody's face.
What the public never investigated was the damage already done. A family butler had told her she was too fat and too plain for any man to love her for anything besides her money. When she asked her father if it was true, he replied that it was probably true.
The seed of body hatred was planted, and it would outlast every marriage and every fortune she ever acquired.
The first predator arrived wearing the costume of a Georgian prince. Alexis Mdivani held no legitimate royal title, but his family had reinvented themselves in the West as the marrying Mdivanis, a brood of five siblings who fabricated pedigrees and married wealthy spouses with the efficiency of a confidence operation. Barbara met him in Biarritz, but the encounter was engineered by his sister, who timed witnesses to discover the couple in bed together.
Barbara fled to Paris in humiliation, and the ultimatum came: marry Alexis or face public scandal.
The wedding took place on June 22, 1933, with Barbara's father providing a $1 million dowry. On the wedding night, Alexis looked at his bride, a healthy woman of 5 feet 4 inches and approximately 148 pounds, and told her she was too fat. Barbara responded by launching a crash diet so severe she lost roughly a third of her body weight in months.
This single sentence became the genesis of the anorexia nervosa that would plague her for the remaining 46 years of her life.
Over two years of marriage, Alexis burned through millions on polo ponies, bespoke clothing, and jewelry. The divorce in March 1935 cost Barbara approximately $2 million. In August of that same year, Alexis was killed in an automobile accident in Spain, leaving an estate of roughly $2 million, almost all of it Barbara's money repackaged under his name.
The second husband was far more dangerous. Count Kurt Heinrich Haugwitz-Hardenberg-Reventlow held a legitimate Danish title and a temper that Barbara would come to know through repeated visits to the hospital. They married in 1935, and Barbara purchased the St.
Dunstan estate in Regent's Park, commissioning the Georgian-style residence she named Winfield House after her grandfather. Their son Lance was born on February 24, 1936, and newspapers proclaimed him the world's richest baby.
The marriage was defined by escalating violence. Reventlow subjected Barbara to savage beatings, one severe enough to hospitalize her and land him in jail. Under the pressure, Barbara began using drugs, specifically the barbiturate Seconal that would define her remaining decades.
Reventlow also persuaded her to renounce her American citizenship in December 1937, taking Danish citizenship for tax purposes, a decision that ignited public outrage.

The divorce proceedings were vicious, centered on custody of Lance, and stretched from 1938 to as late as 1941. At various points, the court awarded Lance to his father, and Barbara, devastated, established a trust fund of several million dollars for the boy. She regained custody in 1945, but by then Lance had spent his formative years in boarding schools, nursing resentment toward his mother and throwing darts at photographs of her cut from tabloid newspapers.
The anorexia that began on her first wedding night now hardened into a clinical condition that left her unable to bear another child.
The third husband was the only one in Barbara's entire life who wanted nothing from her except her company. Cary Grant married Barbara Hutton on July 8, 1942, having first signed a prenuptial agreement stating he wanted no claim whatsoever on her fortune. The press immediately dubbed them Cash and Cary.
Grant was the anomaly in Barbara's romantic history, a man who possessed his own fame and wealth and who genuinely cared about both Barbara and her son Lance, becoming the only one of her seven husbands to bond with the boy.
The marriage nonetheless carried strains neither party could resolve. Grant was intensely private, while Barbara attracted scandal. Barbara could not fathom why Grant insisted on working when her fortune could sustain them indefinitely.
Their home became the setting for continuous parties that Grant resented. The FBI, investigating Barbara under an operation code-named Red Rose for her friendships with suspected Nazi sympathizers, leaked damaging information to journalists throughout the marriage.
The divorce in 1945 involved no financial settlement. Grant neither sought nor received a single dollar, making this the sole marriage among seven in which the Woolworth fortune emerged untouched.
After the war, Barbara returned to London to find Winfield House badly damaged during German bombing. She telephoned her lawyer the following day and donated the entire property, 12 acres in Regent's Park, the second largest private garden in London after Buckingham Palace.
Prince Igor Troubetzkoy, an expatriate Russian described as a painter of modest talent and considerable good looks, married Barbara on March 1, 1947. He was a genuinely accomplished racing driver who piloted the first Ferrari ever to compete in Grand Prix motor racing. The marriage collapsed within a few years, and Troubetzkoy did something none of Barbara's previous husbands had done: he filed for divorce himself.
Barbara attempted to take her own life in the aftermath.
The fifth marriage lasted only 53 days. Porfirio Rubirosa was a Dominican diplomat, race car driver, polo player, and the most notorious playboy of the 20th century. He had already married tobacco heiress Doris Duke, Barbara's lifelong rival, from whom he extracted an annual alimony of $25,000, a fishing fleet, several sports cars, a converted B-25 bomber, and a 17th-century house in Paris.
The wedding took place on December 30, 1953, in the Dominican Republic. Columnist Phyllis Battelle immortalized the occasion: the bride, for her fifth wedding, wore black and carried a Scotch and soda. For the next 53 days, Rubirosa continued his affair with actress Zsa Zsa Gabor openly.
Barbara would later claim the marriage was never consummated.
On February 20, 1954, the marriage was dissolved. Rubirosa received $2. 5 million in cash, the largest privately owned coffee plantation in the Dominican Republic, a B-25 bomber, eight polo ponies, 40 suits, 20 pairs of shoes, and assorted jewelry.
Some accounts cite an additional $1 million gift, bringing the total extraction above $4 million in 1954 dollars, roughly $60,000 per day of marriage.

The sixth husband was the opposite of Rubirosa in every measurable dimension. Baron Gottfried von Cramm was one of the greatest tennis players Germany had produced, ranked number one in the world during the 1930s. He was an anti-Nazi whose defiance cost him a year in prison after the regime charged him with homosexual acts.
Barbara had used her influence to help free him during the late '30s.
They married on November 8, 1955. Those close to von Cramm understood the arrangement: he married her to help her through substance abuse and depression. Von Cramm was attracted to men, and Barbara, who could not accept that his orientation would not change, fell deeply in love with him.
She later told actor Cliff Robertson that von Cramm was the love of her life. The divorce came quietly around 1959 with no large settlement.
The final husband required purchasing a royal title before the ceremony could proceed. By the early 1960s, Barbara had settled on a new companion in Tangier, Pierre Raymond Doan, a Vietnamese man with no royal lineage whatsoever. Barbara solved the problem by paying $250,000 to the former royal family of the Kingdom of Champasak and transforming her companion into Prince Pierre Raymond Doan Vin Na Champasak.
They married on April 7, 1964, in Tangier. The marriage lasted approximately two years before separation.
The aggregate cost of Barbara's marital history, measured across dowries, settlements, gifts, purchased titles, and decades of sustained emotional devastation, represented the single largest drain on the Woolworth inheritance.
The houses Barbara built and discarded tell a parallel story. Sumiya, a Japanese-style palace near Cuernavaca in Mexico, was constructed over six years at a cost of $2. 2 million, featuring a Zen sand garden, a Kabuki theater, and views of the volcano Popocatépetl.
Barbara lived there for a handful of weeks over three years. The property was converted in 1993 into a luxury hotel.
Winfield House was the crown of the collection, donated to the United States government for $1 after the war, creating what remains today the official residence of the American ambassador to the United Kingdom. The Palace of Sidi Hosni in Tangier was her North African retreat, where she hosted legendary parties and widened the surrounding alleys so she could reach her front door by Rolls-Royce.
Barbara Hutton assembled one of the most significant private jewelry collections of the 20th century. The centerpiece was a strand of 44 graduated natural pearls once belonging to Marie Antoinette, purchased by her father from Cartier for approximately $1 million as a wedding gift for the Mdivani marriage. She also acquired the Vladimir emerald tiara, Romanov emeralds that had once belonged to Grand Duchess Maria Pavlovna, and the Pasha of Egypt diamond, which she had recut, willingly sacrificing four carats of an irreplaceable gem because she preferred a different shape.
The collection was ultimately liquidated piece by piece as the fortune collapsed.
The fortune was also consumed from within by the physical destruction that began on a wedding night in Paris. The anorexia never released its hold. The Seconal arrived during the Reventlow years and became the chemical scaffolding holding together a life otherwise collapsing.
Her doctor issued a standing warning that no medication should be left within her reach because if it was, she would consume all of it at once.
Lance Reventlow had grown into a young man of genuine ability, designing and building the Scarab racing cars and earning a reputation that professionals did not extend lightly to wealthy amateurs. On July 24, 1972, Lance boarded a single-engine Cessna 206 near Aspen, Colorado, to survey real estate for a ski resort development. The pilot was a student aviator with only 39 hours of total flight time.

Flying into a storm over the Rockies, the pilot stalled the aircraft, and the Cessna plunged to Earth. All four aboard were killed instantly.
Barbara initially refused to allow her son to be buried. When she finally permitted a funeral attended by Cary Grant, Barbara could not bring herself to go. In the years that followed, she alternated between denying Lance was dead and blaming herself for the crash.
Her staff reported that she could often be heard speaking to her son as though he was standing just beyond her failing line of sight.
By the mid-1970s, Barbara Hutton had retreated to the Beverly Wilshire Hotel in Beverly Hills. The woman who had once hosted a thousand guests at the Ritz-Carlton was now a recluse who rarely left her penthouse suite. She was extremely frail, nearly blind, dependent on a wheelchair, and sustained on high dosages of painkillers and sleep aids.
In 1971, she caught her foot on a carpet and broke her hip, postponing treatment so long that the injury never properly healed.
Oleg Cassini, the fashion designer Barbara had once tried to steal from actress Gene Tierney, visited and left with the definitive portrait of her decline. She was very thin. Gone.
The spirit was gone. The life was gone out of her. She lay in bed drinking Coca-Cola and chain-smoking, speaking to a dead son she could no longer see.
On May 11, 1979, Barbara Woolworth Hutton suffered a heart attack in the penthouse suite of the Beverly Wilshire Hotel and died at the age of 66. The funeral was attended by only 16 mourners. She was interred in the Woolworth family mausoleum at Woodlawn Cemetery in the Bronx.
Biographer C. David Heymann wrote that $3,500 was all that remained in Barbara Hutton's bank accounts at the time of her death. Heymann also pointed to a more specific culprit: Barbara's long-time attorney Graham Mattison, whom the biographer accused of enriching himself at his client's expense to such a degree that when Barbara died with $3,500 in her accounts, Mattison was living like a millionaire.
Barbara had written that she inherited everything but love. By the morning the mortuary attendants arrived at the Beverly Wilshire, the everything had been consumed as thoroughly as the love had been absent.
Her story has a mirror born within days of her in the same city. Barbara Hutton and Doris Duke were born within a week of each other in November 1912 in Manhattan. The press christened them the Gold Dust Twins.
Doris's father told her on his deathbed to trust no one, and she carried that instruction through 81 years, managing her fortune with a discipline that Barbara could never muster. They converged most explosively on Porfirio Rubirosa. Doris married him first in 1947.
Barbara married him five years later and gave him a better bomber, a coffee plantation, and $2. 5 million for 53 days of infidelity.
Barbara died at 66 with $3,500 in the bank and 16 mourners at her service. Doris died at 81, addicted to antidepressants, painkillers, sleeping pills, and alcohol, having installed her Irish butler as executor of a $1.2 billion estate on her deathbed.
One heiress trusted everyone and lost everything. The other trusted no one and kept it all. Neither arrangement produced anything that could be honestly mistaken for a happy life.