Weird History

12 Historic People Who Had Crazy Last Wills  

Peter Dugre
44.7k views 12 items

Some last wills and testaments shatter family bonds, particularly when vast sums of wealth get left to the family dog and not to the humans on the family tree that are hoping to reap the low-hanging fruit of inheritance. Then there are those final wishes handed down by the eccentric that leave executors scratching their noggins and offspring carrying out the bizarre orders of dead relatives. 

The craziest wills in history - some from wills of historical figures, and some just plain weird wills of history from obscure but eccentric individuals who check "write a crazy will" off of their list before kicking the bucket - often leave a lasting legacy of lunacy. In death, some of these crazy will writers cemented their quirks for posterity by continuing their march to a beat of different drummer into the afterlife. 

Leona Helmsley is listed (or ranked) 1 on the list 12 Historic People Who Had Crazy Last Wills
Photo: United States Marshals Service/Wikimedia Commons/Public Domain

Nicknamed "The Queen of Mean," Leona Helmsley had a soft spot in her hard heart for her pooch, a white Maltese named Trouble. While the hotel heiress and businesswoman minced no words in denying two of her grandchildren access to her vast wealth in her last will and testament, she left the dog $12 million when she died in 2007. The overlooked grandchildren fought the will and lost, all while the dog was afforded a security detail that cost $100,000 annually to protect its life from would-be assassins.

A majority of Helmsley's assets upon death (at least $5 billion) went to charities, including those supporting animal welfare. A judge eventually reduced the $12 million doggy treat to $2 million, ordering that the difference be added to the charitable giving. In the will, Helmsley, who had spent 18 months in prison in the 1990s for tax evasion, stated that the grandchildren were well aware of why she had stiffed them.

When Trouble yelped his last yelp in 2007, he was placed at Helmsley's side at their Westchester, New York, mausoleum. Her will had also left $3 million for the annual steam-cleaning of her forever resting spot. 

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Harry Houdini is listed (or ranked) 2 on the list 12 Historic People Who Had Crazy Last Wills
Photo: Famous Players-Lasky Corporation/Wikimedia Commons/Public Domain

Harry Houdini was an escape artist and before his death, he arranged to pull off the grandest of escapes. When he died in 1926 from a ruptured appendix (fittingly, on Halloween), he had already laid the groundwork for a miraculous return by ordering his wife, Bess, to hold an annual séance. The two shared a secret code, which Houdini was to relay through a medium to her in order to prove that it could only be his spirit. His will specified any medium who could reach Houdini in the afterlife would be rewarded $10,000.

History says Houdini may have had mixed motivations for the annual séances. He had dedicated much of the latter years of his stage shows to debunking the tricks of mediums by duplicating their abilities on stage. He had been disappointed in attempts to contact his own dead mother and sought to expose those claiming to contact the dead as frauds.

The séances continued for 10 years after Houdini's death, but the great escape artist never pulled off the greatest trick of bridging the divide back into the living world. His enduring fans still hold séances hoping that given time, the master will again defy all odds.

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Charles Vance Millar Filled His Will with Some Very Expensive Gags
Charles Vance Millar is listed (or ranked) 3 on the list 12 Historic People Who Had Crazy Last Wills
Photo: Unknown/Wikimedia Commons/Public Domain

Canadian millionaire Charles Vance Millar found a richness in humor almost as great as in the money he earned in life through sound investment and practicing law. He died on Halloween 1926, but it might have been more fitting for the date to have been April Fool's Day, for his last will and testament was loaded with gags, chief among them bequeathing his fortune to a Toronto family that could birth the most children over a 10-year period following his death.

The race for Millar’s fortune, widely covered in newspapers at the time, became known as the Stork Derby and eventually had six Toronto families earning the equivalent of at least $200,000 in today’s Canadian money for their efforts in having at least nine children. Four families received $2 million in today’s money, but two other families left out fought for their reward in court before getting the $200,000 share. In particular, a family that produced three stillborn babies, which would have upped its total to 11 babies, finally saw the fruits of the labor after a court ruled to count the deceased children.

Millar might have underestimated how motivated competitors would be when he penned the will. He hadn’t banked on the Great Depression making the opportunity he bestowed upon Toronto families all the more attractive. Dozens entered the running to reproduce like hares.  

He also had outlined several other ironic wishes in his will. He left a home (an island getaway in Jamaica) to three men who hated each other. To people known to oppose gambling, he left interests in a jockey club. To teetotalers, he left his shares in a brewery. That’s rich.

John Porter Bowman Built a Mansion Complete with Staff to Enjoy After His Resurrection

A tanner from Vermont, John Porter Bowman had an optimistic view of the afterlife, perhaps due to the melancholy and morbid perspective he gained during life. His wife and daughters had died before him, so he dedicated much time to an ostentatious mausoleum and 21-room mansion in their honor. When he died in 1891 and was to join them in their decked-out tomb, he also ordered that the mansion be staffed and kept up as if the family was returning home each evening. 

Bowman believed once he ceased to exist, they’d all return to the living. To staff the family home, Bowman set up a $50,000 trust and specified that meals be prepared daily in order to have food ready to serve the hungry reincarnated who had endured the passage back to the living world. Servants maintained the ghostly estate and their employment from Bowman’s death in 1891 to 1950. It's no surprise that the estate is rumored to be haunted.