Stupid Cupid: 5 Love Stories that Ended in the Landfill

February 7, 2024

While many love stories bleed sap with a “happily ever after,” some famous fairy tales have taken a sour turn, leading to financial ruin for the lovebirds involved. These stories illustrate how the intersection of love, wealth, and inheritance can create complex legal and financial situations for those involved. Here are five such fairy tales with such unfortunate endings.  Happy Valentines Day!

  1. Anna Nicole Smith and J. Howard Marshall

Former Playboy Playmate Anna Nicole Smith married billionaire oil tycoon J. Howard Marshall, who was over 60 years her senior. The legal battles over Marshall’s estate, which continued even after his death in 1995, drained significant financial resources from both Smith and Marshall’s family.  Anna Nicole then passed away suddenly on February 8, 2007, at the Seminole Hard Rock Hotel & Casino in Hollywood, Florida, as a result of an accidental drug overdose. Following her death and a whole 16 years after the death of J. Howard Marshall, the case has finally been decided through the U.S. Supreme Court.

A narrowly divided court decided 5-4 that the bankruptcy court did not have jurisdiction to essentially try a probate case.  Smith’s estate lost its claim to any portion of the Marshall estate, leaving all the funds to the Marshall family.  We will never know the true wishes of J. Howard Marshall in regard to Anna Nicole Smith.  Perhaps he did intend for her to have a portion of his estate.  It serves as a reminder to plan properly and keep your documents current with the changes in your life.

  1. Leona Helmsley and Harry B. Helmsley

Leona Helmsley, dubbed “The Queen of Mean” presents the truism that money does not buy happiness. Born in 1920 in Brooklyn, Leona became a successful condominium broker in Manhattan, eventually elevating herself at a firm owned by Harry B. Helmsley, one of the city’s biggest real-estate developers. The two married in 1972, and Leona became the public face of their empire, the self-styled “queen” of the Helmsley chain of hotels. Helmsley’s image became a symbol of the celebration of wealth in the 1980s. In private, Leona was known for being a despot. She left a trail of ruin—embittered relatives, fired employees, and, fatefully, unpaid taxes. In 1988, the U.S. Attorney’s office charged the couple with income-tax evasion, among other crimes. (Harry Helmsley avoided trial because of ill health; he died in 1997, at the age of 87.) Leona was convicted of multiple counts and served 18 months in federal prison.

After her husband died, Leona Helmsley got a dog named Trouble, a Maltese “bitch.” In her will, which she signed two years before her death, Helmsley put aside twelve million dollars in a trust to care for Trouble. Further, she directed that, when Trouble died, the dog was to be “buried next to my remains in the Helmsley Mausoleum,” at Sleepy Hollow Cemetery, in Westchester County. Helmsley made only a handful of relatively small individual bequests in the will, and left the bulk of her remaining estate to the Leona M. and Harry B. Helmsley Charitable Trust.

  1. Doris Duke and Eduardo Tirella

Tobacco heiress Doris Duke, one of the wealthiest women in the world, had a brief and controversial relationship with her close confidant and interior designer, Eduardo Tirella. In the fall of 1966, Doris Duke is alleged to have killed Tirella in Newport, Rhode Island. Local police ruled the incident “an unfortunate accident.” Half a century later, compelling evidence suggests that the mercurial, vindictive tobacco heiress got away with murder.

Rumor has it that Tirella was planning to sever his professional ties with Duke for good and flew to Rhode Island to tell her face-to-face. Tirella and Duke had a heated argument, overheard by the estate’s staff. The pair got into the station wagon with Tirella behind the wheel and as Tirella stopped the car and got out to unlock the gate, Duke slid into the driver’s seat and hit the accelerator.  Tirella’s body soon lay crushed under the rear axle.

After Tirella’s death in a car accident on Duke’s estate, legal battles ensued over his inheritance. This situation contributed to Duke’s public image and affected her financial standing. When the tobacco heiress died in October 1993, she left a will that shocked even those closest to her. Ignoring Chandi Heffner, the latter-day flower child whom she adopted in 1988, Duke left control of the bulk of her fortune to Bernard Lafferty, her butler of six years.

  1. Antony and Cleopatra

The tragic love story of Antony and Cleopatra is a renowned narrative within the annals of ancient history. It was one of William’s Shakespeare’s most famous plays, performed around 1607.  Mark Antony, a Roman general, and triumvir (one of three men who ruled the Roman empire as a team), and Cleopatra, the Queen of Egypt, became entangled in a passionate and tumultuous love affair during the later years of the Roman Republic. Cleopatra is notorious for being a flirt and having charmed some of the great men of her era, including Caesar.  Despite her coquettish disposition, Antony loved her passionately.  The two formed a political and military alliance; however, their love faced intense opposition from political rivals in Rome, particularly Octavian (later known as Augustus Caesar), who viewed Antony’s relationship with Cleopatra as a threat to Rome.

The decisive naval Battle of Actium in 31 BCE marked a turning point in their story. Antony loses the battle as his troops deserted him and he denounces Cleopatra and resolves to kill her. Cleopatra decides that the only way to win back Antony’s love is to send him word that she killed herself, dying with his name on her lips. She locks herself in her monument and awaits Antony’s return. Her plan backfires: rather than rushing back in remorse to see Cleopatra’s body one last time, Antony decides to take his own life. He begs one of his aides, Eros, to run him through with a sword, but Eros refuses and kills himself. Antony admires Eros’ courage and attempts to do the same, but only succeeds in wounding himself. In great pain, he learns that Cleopatra is indeed alive. He returns to Cleopatra, is hoisted up to her in her monument and dies in her arms.  Cleopatra, devastated by Antony’s death, also died by suicide. According to popular accounts, she allowed herself to be bitten by an asp, a venomous snake. The tragic end of Antony and Cleopatra’s love story symbolizes the clash between personal desires and political responsibilities, leading to a series of events that played a role in the transformation of the Roman Republic into the Roman Empire under the rule of Octavian.

  1. Napoleon Bonaparte and Joséphine de Beauharnais

Joséphine, whose real name was Marie-Josèphe-Rose Tascher de La Pagerie (Napoleon gave her the name Joséphine based on her middle name), grew up on a plantation in the French Caribbean colony of Martinique. When she was in her teens, her family married her off to a minor French nobleman, Alexandre de Beauharnais. He became a victim of the state-sanctioned violence of the French Revolution’s Reign of Terror and was guillotined in 1794. Joséphine managed to barely miss being guillotined as well (due to good luck in timing).  Joséphine was now a 32-year-old widowed mother of two (and social climber). After a series of affairs with a number of senior political figures, Napoleon showered her with gifts and won over her children with his playfulness. He was madly in love.  The jury is still out on her devotion to him.

Napoleon and Joséphine both had affairs during their marriage, and the arguments began. Napoleon threatened divorce on several occasions, mainly on the grounds that Joséphine had not produced an heir. The failure to produce an heir continued to trouble their marriage, and when Napoleon’s mistress Eléonore Denuelle gave birth to his child in 1806, it was clear that the problem lay with the 43-year-old Joséphine. Eventually, his marriage to Joséphine was annulled, but at the divorce ceremony on December 15, 1809, the couple read statements of devotion to each other, confirming their mutual love. Napoleon married Marie-Louise of Austria in March 1810. Exactly one year later, she gave birth to the long-awaited heir, Napoleon II.

Joséphine died from pneumonia in 1814. Napoleon ultimately died in exile and his last words are reputed to have been, “France, the army, head of the army, Joséphine.” Despite their multiple affairs, tempestuous arguments, and public divorce, it seems the love between Napoleon and Joséphine never died.

What do all these love stories have in common?  Jealousy, feuding, and family strife.  If this sounds familiar, you need to get your estate plan in order so that your family will be protected upon your death.  No matter where Cupid’s arrow takes you.  Our exclusive focus lies in estate planning, ensuring you peace of mind about your family once you are no longer here. Contact OC Estate and Elder Law at (954) 251-0332 or to get started with your free consultation. Our attorneys are fluent in English, Spanish and Russian.