Many would agree it’s a dog-eat-dog world out there, where hustling, cutting corners, and telling the occasional white lie can help you get ahead and stay on top. Of course, some people push the envelope too far. Here are eight of the most notorious con artists, grifters, and swindlers from the 19th century onward.
American actress Phoebe Cates in the film Princess Caraboo (1994).
Princess Caraboo
In April 1817, the residents of Almondsbury, England, were surprised to find a mysterious woman in a shawl and colorful dress wandering around their village. She spoke an indecipherable language, though she seemingly referred to herself as “Caraboo,” and her recognition of exotic fruits like pineapples suggested that she came from Asia. Eventually, a Portuguese sailor agreed to “translate” for the stranger, relaying the information that she was a princess from the Indian Ocean island of Javasu who had escaped a kidnapping attempt by pirates.
The woman lived comfortably for the next few months at the home of an Almondsbury magistrate, where she showed off her native style of dancing and religious worship to curious visitors until a landlady in nearby Bristol revealed that Princess Caraboo from Javasu was really Mary Willco*cks from Devon. Apparently, the townspeople didn’t take the news too badly, as Willco*cks avoided imprisonment and even got the magistrate’s wife to pay for her trip to America. She later returned to England, married, and settled down in a legitimate business of importing and selling leeches for medical purposes.
George C. Parker
The expression “If you believe that, I have a bridge to sell you” is supposedly a nod to American con man George C. Parker, who made a living as a purveyor of New York City’s Brooklyn Bridge through the late 19th and early 20th centuries. As described in Carl Sifakis’s Hoaxes and Scams: A Compendium of Deceptions, Ruses and Swindles, Parker typically won over unsuspecting immigrants with offers to work in a yet-to-be-built toll booth before smoothly convincing them of the potential of buying the bridge outright. Occasionally, this resulted in police shutting down construction work from the confused victims who were trying to get their toll booths up and running.
Parker also sold phony deeds to other city landmarks like the Statue of Liberty, Madison Square Garden, and the Metropolitan Museum of Art, though he remained most proud of his continued success with the famous bridge. It was a forged check that finally brought an end to his grifting. His lengthy arrest record led to a lifetime prison sentence in 1928, though he reportedly enjoyed his incarceration thanks to the deference shown by admiring younger inmates.
Elizabeth Bigley/Cassie L. Chadwick
Life on the straight and narrow was never in the cards for Elizabeth Bigley, who went by numerous aliases while defrauding banks and deep-pocketed investors through the Northeast and Midwest for more than two decades. Alternately posing as an heiress and a clairvoyant, Bigley first encountered trouble in the 1890s, when she was imprisoned in Ohio for three and a half years for forging checks.
Reappearing in Cleveland at the end of the decade, she married a wealthy widower and proceeded to burn through his money, purchasing expensive clothes, jewelry, and furniture. But a lavish domestic lifestyle wasn’t enough for the grifter, now known as Cassie L. Chadwick. She started a rumor that she was the illegitimate daughter of steel tycoon Andrew Carnegie, through which she was able to access loans and cash advances from an increasing number of lenders. One bank owner smelled something rotten by late 1904, however. Her failure to repay the $190,000 promissory note caused the web of lies to collapse. Following a high-profile trial in early 1905 that drew a curious Carnegie out to Cleveland to see the proceedings for himself, Chadwick died after less than a year in prison.
Charles Ponzi
An Italian immigrant hustling to make ends meet in Boston, Charles Ponzi founded the Securities Exchange Co. in 1919 on the premise that international reply coupons purchased overseas could be redeemed for far greater value in the United States. Promising returns of 50 percent in 45 days, the dapper businessman lured approximately 20,000 investors into paying $10 million, a windfall that enabled him to pay for a mansion and limousine driver.
Of course, Ponzi was using the influx of new investors to pay promised returns to existing ones. His scheme came crashing down after his ostentatious displays of wealth drew closer scrutiny from journalists and federal investigators. Arrested in August 1920 on 86 counts of mail fraud, Ponzi spent most of the next 14 years behind bars and lived out his final days in poverty in Brazil. Still, he spoke of the excitement of having orchestrated such a successful scheme, an experience that other Ponzi scheme perpetrators like Bernie Madoff might relate to.
Frank Abagnale Jr.
Few tales of high-wire deception are more engaging than that of Frank Abagnale Jr. Starting in the mid-1960s, according to Abagnale’s own account, the 16-year-old “Skywayman” hitched rides all over the globe while disguised as a Pan Am pilot, cashing in some $2.5 million in phony checks along the way. He also claims to have passed himself off as a doctor, an assistant district attorney, and a college professor until finally getting nabbed in France in 1970.
After four years behind bars, a reformed Abagnale began sharing his expertise at the FBI National Academy, churned out a 1980 memoir titled Catch Me If You Can, which became a Leonardo DiCaprio/Tom Hanks-led film in 2002, and forged a lucrative career as a security consultant and public speaker.
Or so the story goes. According to Alan C. Logan’s 2020 book The Greatest Hoax on Earth: Catching Truth, While We Can, Abagnale actually operated on a far smaller scale, stealing from just a few families and businesses before getting busted. In other words, the con man’s greatest hoax may have been convincing everyone that he pulled off all the glamorous heists in the first place.
Lee Israel
For a while, Lee Israel carved out a successful living as a biographer, even cracking the New York Times best-seller list with her 1980 book on journalist Dorothy Kilgallen. But as it turned out, her talents lay in the impersonation of the literary figures she so admired. For about a year and a half in the early 1990s, Israel composed and sold some 400 letters in the epistolary styles of Dorothy Parker, Ernest Hemingway, Noël Coward, and others, using the specific vintage typewriter each writer favored. Then, after memorabilia dealers caught wind of her efforts, she turned to stealing the real letters from private collections and replacing them with her carefully constructed duplications.
The FBI finally closed shop on her operation in 1993, though she wound up with a relatively lenient sentence of six months of house arrest and five years of probation. Israel also leveraged her notoriety into one final book deal, a 2008 memoir titled Can You Ever Forgive Me?, which became an Academy Award-nominated movie starring Melissa McCarthy the following decade.
Anna Delvey
Although many people adopt something of a cosmopolitan identity after moving to a new city, Russian-born Anna Delvey (born Anna Sorokin) took shape-shifting to an extreme degree. Delvey first appeared in New York City in 2013 after completing fashion internships in Europe and convinced many colleagues that she was a wealthy German heiress. Her eccentricities covered an inability to pay for expensive dinners and parties. The ruse proved good enough to arrange for long-term lodging in a swanky downtown hotel, and the would-be heiress even attempted to use made-up assets to acquire millions of dollars in loans to fund a glamorous new arts center.
Ultimately, she was done in by her failure to pay her hotel bills and the frustration of a spurned friend, who got stuck with the $60,000-plus tab for a lavish vacation. Delvey was arrested in Los Angeles in October 2017. Convicted on eight counts of grand larceny and theft of services in April 2019, she spent another two years in prison and wound up in the custody of U.S. Immigration and Customs Enforcement shortly after being paroled. Delvey was reportedly paid $320,000 by Netflix for the rights to turn her adventures into the 2022 limited series, Inventing Anna.
Simon Leviev
Born Shimon Hayut in Israel, Simon Leviev fled his home country in 2011 to escape theft and forgery charges, only to be imprisoned for two years in Finland for defrauding three women. Hayut later resurfaced in Europe under his new name, allegedly to pass as a son of diamond mogul Lev Leviev, and proceeded to trick several women he met on Tinder into parting with credit card numbers and loans that were never repaid.
Apprehended in Greece in 2019, Leviev was extradited to stand trial in Israel for the 2011 charges—not the estimated $10 million he stole from various girlfriends—and spent just five months behind bars. His story also earned the Netflix treatment in the form of the 2022 documentary The Tinder Swindler. While the exposure led to his expulsion from dating sites and a lawsuit filed by the Leviev diamond family, Hayut has since signed with a Hollywood agent and wants to appear on his own dating show.
