Weird History

11 Historic People Who Had Crazy Last Wills 

Peter Dugre
Updated February 27, 2020 52.7k views 11 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 fruits 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 deceased relatives. 

The craziest wills in history - like the 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 the beat of a different drummer into the afterlife. 

Leona Helmsley is listed (or ranked) 1 on the list 11 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 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 passed in 2007. Two other grandchildren were offered $5 million each and her brother also received a large fortune. The dog, however, was given the largest sum and afforded a security detail to protect its life from would-be kidnappers and assassins.

A judge eventually reduced the $12 million doggy treat to $2 million, but Trouble still got to live a life of luxury with a caretaker in a hotel in Florida. When Trouble yelped his last yelp in 2011, he was placed at Helmsley's side in her Westchester County, NY, mausoleum. Her will had also left $3 million for an annual washing or steam-cleaning of their forever resting spot. 

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Harry Houdini is listed (or ranked) 2 on the list 11 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 passing, he arranged to pull off the grandest of escapes. When he passed in 1926 from a ruptured appendix (fittingly, on Halloween), he had already laid the groundwork for a miraculous return by asking his wife, Bess, to hold a yearly séance on the anniversary of his demise. 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. While this wasn't stipulated in Houdini's official will, it was a pact Bess tried to follow after her husband passed. 

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 11 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 passed on Halloween in 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 a fortune (about $9 million) to a Toronto family that could birth the most children over a 10-year period following his passing.

The race for Millar’s fortune, widely covered in newspapers at the time, became known as the Stork Derby. In the end, six Toronto families cashed out - dividing the money through lawyers and lawsuits. Four families with at least nine children received $2 million (in today’s money), while two other families with similar numbers of offspring fought for their reward in court. In one sad instance, a family that produced three stillborn babies, which would have upped its total to 11 children, was first denied the prize and then given a $200,000 settlement. A similar thing happened to a mother who had produced 10 children with two men but found that the judge considered them illegitimate.

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 for the chance at money.  

He also 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 Mausoleum And Mansion To Be Enjoyed After His Passing

A tanner and salesman from Vermont, John Porter Bowman may have had an optimistic view of the afterlife, perhaps due to the melancholy and morbid perspective he gained during life. His wife and daughters had passed before him, so he dedicated much time to an ostentatious mausoleum in their honor and a home called Laurel Hill across the street. When he passed 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. 

In his will, Bowman set up a $50,000 trust to maintain his property so that his home, grounds, and mausoleum remained just as he had left them while alive. This led to local legends that Bowman believed in reincarnation or other afterlife visitations. It's no surprise that the estate is rumored to be haunted.