In December 1910, 25-year-old Dorothy Arnold left her family’s Manhattan home to buy an evening gown and a few books. She wore an expensive blue sergeNaN

Some heiresses are born into unimaginable wealth, yet their fortunes bring them anything but happiness. Gloria Vanderbilt, born in Manhattan on February 20, 1924, was the inheritor of one of America’s greatest dynasties. Her father, Reginald Claypoole Vanderbilt, was a great-grandson of Cornelius Vanderbilt, the railroad and shipping titan who had been the richest man in America. Reginald was an alcoholic who squandered much of his inheritance on horses and gambling.

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He died of cirrhosis in September 1925, when Gloria was just eighteen months old. He left his estate, valued at roughly five million dollars—about a hundred million today—in trust for Gloria and a half-sister, with Gloria’s mother, Gloria Morgan Vanderbilt, as trustee. In 1934, Gloria’s aunt, Gertrude Vanderbilt Whitney, sued her mother for custody, arguing that the widow was unfit. The trial was a sensation, splashing details of the mother’s lavish life in Paris and London and a rumored lesbian affair across the newspapers.

Gloria, then ten years old, was called to testify behind closed doors. When the verdict came, her mother was deemed neglectful. Custody passed to her aunt, who also took control of the trust. The relationship between mother and daughter never fully recovered, and in 1946, the young Gloria cut off her mother’s annual allowance, telling her to find work and donating the money to charity instead.

Gloria grew into a strikingly beautiful young woman. After enduring the rigid life under her aunt’s care, she moved to Hollywood at seventeen and married a talent agent, Pat DiCicco, who was abusive and left her bruised and psychologically damaged. They divorced in 1945, but the marriage had already cost Gloria her place in her aunt’s will. Gertrude Whitney died in 1942, having disinherited her niece.

A day after divorcing DiCicco, Gloria married the sixty-three-year-old conductor Leopold Stokowski, more than three times her age. That marriage lasted a decade and produced two sons before ending in 1955. A brief marriage to director Sidney Lumet—who launched his legendary career the following year with Twelve Angry Men—ended in 1963. Her fourth and final husband, screenwriter Wyatt Emory Cooper, died of a heart attack in 1978.

Along the way, she was linked to Marlon Brando, Frank Sinatra, and Howard Hughes and reportedly to children’s author Roald Dahl, often while she was married to others. Gloria, however, was more than her romantic history. In the 1970s she launched a wildly successful line of designer jeans and eventually expanded into clothing, accessories, and perfume, building a genuine business empire. In later years she rediscovered her first loves—painting and writing.

She published six volumes of memoirs and three novels, and in 1989 her life was chronicled in the biography Little Gloria… Happy at Last, which examined the custody battle that had defined her childhood. Gloria Vanderbilt died at her Manhattan home on June 17, 2019, of stomach cancer at the age of ninety-five. A different kind of tragedy unfolded in the life of Huguette Clark, born in Paris on June 9, 1906, the daughter of William A.

Clark, a copper and railroad magnate who had served as a U. S. senator from Montana. Clark’s fortune was estimated at three hundred million dollars when he died in 1925.

Huguette had been raised in Paris, attending the coronation of King George V in 1911 before being sent to America for school. When her father died, she inherited roughly fifty million dollars. She married a law student in 1928; the marriage lasted less than a year. Afterward she settled into a vast apartment on Fifth Avenue, overlooking Central Park.

Over time, Huguette became increasingly reclusive, distrusting strangers and preferring to speak French so those around her could not understand her. Her good deeds were often anonymous, and she rarely visited the properties she kept paying to maintain. After her mother died in 1963, her isolation deepened. By the 1980s, she was nearly invisible to the world, and many assumed she was dead.

In 1991, her health failed so badly that she was admitted to a Manhattan hospital, where doctors discovered she had not seen a physician in two decades. Her face was disfigured by untreated cancerous lesions, her mind was clouded, and she was severely malnourished. After reconstructive surgery, she chose not to return home. She began paying the hospital nearly a thousand dollars a day to stay, later moving to Beth Israel Medical Center, where she occupied a private room overlooking the park she had once lived above.

She spent the final twenty years of her life there, attended by a private nursing staff, never once contacting the servants who continued to maintain her Fifth Avenue apartment, her Santa Barbara estate, or the Connecticut mansion she had never lived in. She spent her fortune liberally. A lifelong friend received ten million dollars, and her private nurse, Hadassa Peri, received more than thirty million in gifts and bequests. In one instance, Huguette handed the technician who repaired her hospital television twenty-five thousand dollars.

When she died on May 24, 2011, at the age of 104, her estate was worth three hundred million dollars. A first will leaving the majority of her fortune to her extended family—people she had rarely seen for decades—was swiftly replaced by a second will directing three-quarters of the estate to charities and large sums to her nurse. Family members sued, arguing that the elderly and mentally fragile Huguette had been coerced. The court agreed, and the first will was reinstated.

The family ultimately received more than seventy-five percent of the estate, while Hadassa Peri was forced to return thirty million dollars as part of a settlement. Barbara Hutton’s wealth came from her maternal grandfather, Frank Winfield Woolworth, founder of the five-and-dime store empire. Born in New York on November 14, 1912, Barbara had a deeply troubled childhood. Her father was a serial womanizer and heavy drinker, and in May 1917 her mother died suddenly of a reported infection—though many suspected suicide, especially since five-year-old Barbara was the one who found the body.

In 1919 her grandfather died, and when her grandmother followed in 1924, Barbara inherited a third of the Woolworth fortune. The sum grew in her father’s careful hands, and when she gained full control in the early 1930s, it was worth over fifty million dollars. Her coming-of-age party in November 1930, which included a performance by crooner Rudy Vallee and cost more than sixty thousand dollars, was roundly condemned in the press as the Depression ravaged the nation. The newspapers dubbed her the Poor Little Rich Girl, a label that would haunt her.

Her adult life was defined by seven marriages. Her first husband, the Georgian-born opportunist Alexei Mdivani, had his eye on her money and burned through a fortune before she divorced him in 1935. Her second husband, Danish nobleman Kurt von Haugwitz-Reventlow, was physically and emotionally abusive. She began drinking heavily, developed anorexia, and gave birth to her only child, Lance, in 1937.

Her third husband was Cary Grant; the marriage was comparatively happy but short-lived, ending in 1945. Her fourth, Prince Igor Troubetzkoy, used her money to fund his racing career until their divorce in 1951, after which she attempted suicide. Her fifth marriage, to Dominican diplomat Porfirio Rubirosa—the ex-husband of her rival heiress Doris Duke—lasted just fifty-three days, though Rubirosa still walked away with a hefty settlement. Her sixth and seventh marriages, to tennis champion Gottfried von Cramm and Prince Raymond Doan Vinh na Champassak, both ended in divorce by the mid-1960s.

By then, her health was deteriorating from addiction and anorexia, and much of her fortune had been spent, squandered, or lost to unscrupulous partners. In 1972, her son Lance was killed in a plane crash. Barbara retreated to a suite at the Beverly Wilshire Hotel, addicted to painkillers and alcohol, nearly blind. She died of a heart attack there on May 11, 1979, at sixty-six, with only three thousand five hundred dollars left in her name.

Christina Onassis was born on December 11, 1950, into one of the greatest business dynasties of the twentieth century. Her father, Aristotle Onassis, had risen from modest beginnings in Smyrna to become the world’s most powerful shipping magnate, expanding into aviation, casinos, and oil. Her mother, Tina Livanos, was the daughter of his fiercest rival, Stavros Livanos. Christina’s childhood was global—homes on three continents, servants rather than parents, and a cold, unraveling marriage between her father and mother, which ended in divorce in 1960.

That same year Aristotle began his long affair with opera singer Maria Callas, and in 1968 he married Jacqueline Kennedy, the widow of the assassinated president. Christina and her brother Alexander resented their stepmother, whom Christina dismissed as her father’s unfortunate obsession. On January 22, 1973, Alexander, an experienced pilot, took a small seaplane for a training flight from Athens. The aircraft crashed shortly after takeoff, and Alexander, just twenty-four, died the next day.

Christina became the heir. Her father grew paranoid, convinced the CIA had killed his son, and her mother, increasingly dependent on prescription drugs, died in October 1974 from a drug overdose, widely believed to be suicide. Six months later, on March 15, 1975, Aristotle Onassis himself died in Paris, his will to live gone after his son’s death. Christina lost her parents and her only brother in less than two and a half years.

She inherited an empire worth roughly six hundred million dollars and a controlling interest in the Onassis business. She sold off parts of the empire, donated other pieces to charity, and kept the shipping and aviation core. Her personal life was chaotic. She married four times: a real estate tycoon nearly twice her age, two shipping heirs, and finally Thierry Roussel, a Frenchman from a wealthy pharmaceutical family, who was unfaithful and fathered two children with his mistress during the marriage.

In 1985, she gave birth to her only daughter, Athena. Depressed and increasingly dependent on prescription drugs, Christina died in a bathtub at a friend’s home in Argentina on November 19, 1988, at thirty-seven, reportedly of a heart attack exacerbated by drug use. She was buried beside her father and brother. Her daughter Athena inherited the two-hundred-fifty-million-dollar estate when she turned eighteen in 2003.

Finally, there is the mystery of Dorothy Arnold, born in New York on July 1, 1885, into a wealthy importing family. She graduated Bryn Mawr in 1905 and aspired to be a writer, but her stories were repeatedly rejected and her family mocked her ambitions. On the morning of December 12, 1910, she told her mother she was going to Fifth Avenue to buy an evening dress and a few books. Around two in the afternoon, she met a family acquaintance outside of a bookstore, gave her a letter to deliver, and mentioned she planned to walk home through Central Park.

That was the last time anyone who knew her ever saw her. She never arrived for dinner. Her family, fearing a scandal, delayed reporting her disappearance for weeks, though they hired private detectives. On January 25, 1911, after six weeks without a trace, her father held a press conference and offered a thousand-dollar reward.

Theories abounded: murder in the park, a secret romance, and, after a cruel prank postcard arrived claiming she was safe, a hoax. It was suggested she had been pregnant and died from a botched abortion, though this was never substantiated. Her family suspected suicide. Her father spent over two hundred fifty thousand dollars searching for her before his death in 1922.

Reports of sightings continued for decades, but none was ever confirmed. Dorothy Arnold vanished without a trace, and the truth of her fate was never discovered.

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