It takes a special kind of person to pull off a con with just the right amount of charm, a dash of smarts, and a lot of luck. Throughout history, these diabolical deceivers have pulled off some amazing schemes, swindling people out of millions of dollars and in some cases even more. So today, we’re going to trick you into learning about the biggest scams in history. Let us know in the comments what other historical hustlers you want to hear about!
The Original Ponzi Scheme
Everyone's heard of a Ponzi scheme, but where did the Ponzi part of the name come from? The strategy was invented by Italian immigrant Charles Ponzi in the early 20th century. He landed in the land of opportunity with no money and a pocket full of dreams—oh, sorry, that's a pocket full of schemes. After setting up a business called the Securities Exchange Company, Ponzi started offering investments that would pay back 100% interest after 90 days.
In a classic robbing Peter to pay Paul scenario, Ponzi used money from one investor to pay off another, rinse and repeat. This illusion of a never-ending flow of cash lasted for two years, with Ponzi raking in $250,000 a day before he was eventually caught. His investors ended up losing about $20 million in the scheme.
The Master of Disguise: Frank Abagnale Jr.
When you're particularly proficient at committing crimes, the authorities define you as a career criminal. Such was the case for Frank Abagnale Jr., whose name you might know from the Steven Spielberg movie Catch Me If You Can. He was a con man who successfully posed as a doctor, airline pilot, college professor, and even a lawyer—not all at the same time, mind you.
Throughout the 1960s, Abagnale passed about $2.5 million worth of fake checks all over the world. He was eventually caught, served his time, and was released. In an irony of all ironies, he opened Abagnale & Associates, which helps companies detect fraud. However, author Alan C. Logan released a 2020 book called The Greatest Hoax on Earth, suggesting that Abagnale’s story of being on the run from ages 16 to 20 was complete fiction. Public records obtained by Logan show that Abagnale was actually confined in prison during those years.
Bernie Madoff: The Modern Ponzi Master
Let's chat a bit about Bernie Madoff, who took the Ponzi scheme and dialed it up to $65 billion. Madoff conned over 1,300 investors over several years, destroying most of his victims financially. Several of his victims were prominent Hollywood figures like Kevin Bacon, Larry King, and even Steven Spielberg, who you’d think would know better after Catch Me If You Can.
With the promise of suspiciously high returns on their money, who wouldn’t immediately invest with Madoff? Since he was able to use one investor's money to pay off another, nobody ever questioned his claims, allowing him to pocket the extra money. Madoff was famously arrested and convicted in 2008 and sentenced to 150 years in prison, serving until his death in 2021.
The Anastasia Impostor
During the Russian Revolution in July of 1918, Tsar Nicholas II and his family were imprisoned in a basement when the call came to have them executed. Russian revolutionaries carried out the regicide in a hail of bullets, which vanquished the whole family in one fell swoop—if you believe the official story. Real Anastasia fans believe that the young Grand Duchess survived the firing squad and lived on. No one wanted people to believe that more than Anna Anderson.
Two years after the murder of the Tsar's family, Anna started claiming she was their youngest daughter, Anastasia. According to Anderson, two brothers carried her to safety the night of the shooting and transported her to Romania. None of the Romanov relatives believed this story, but the court of public opinion saw some prominent supporters on her side. Her harrowing tale was the basis for the 1956 Ingrid Bergman film Anastasia and continued to be a well-known point of contention until Anderson’s death in 1984. A post-mortem DNA test finally confirmed that her story was completely false.
The Great Impostor: Ferdinand Waldo Demara
We’d love to tell you definitively that Ferdinand Waldo Demara was born in 1921, but with a guy known as "The Great Impostor," no one can actually be sure that's true. We do know he had a high IQ, a photographic memory, and a penchant for stealing identities. Over the years, he pulled off convincing impressions of a zoologist, a civil engineer, a prison warden, and even a Benedictine monk—and that’s just a small sample.
His downfall finally came during the Korean War while he was posing as a doctor on a Royal Canadian Navy destroyer. Several wounded men were brought in to have their injuries tended to, and to his credit, Demara was able to bluff his way through multiple life-saving surgeries using a textbook as a guide. News started to spread of his heroism, and the more people learned about this war hero, the more they realized he was full of baloney. He became too famous to continue his shenanigans after that, especially once Tony Curtis played him in a movie called The Great Impostor.
Lou Pearlman: The Boy Band Con
There’s no shortage of stories about scheming, conniving Hollywood managers, and Lou Pearlman interpreted that as part of the job description. While you may not recognize his name, you definitely recognize his clients, whether you wanted to or not. He was the man behind the Backstreet Boys and NSYNC, either of which could generate enough revenue on their own to pay for a thousand lifetimes of luxury living.
But the entire time Pearlman was managing successful boy bands, he was also getting friends and family to invest in bogus business ventures with names like Transcontinental Airlines. Many of the people investing were elderly and lost their life savings because of his dirty dealings. He was arrested in 2007 and sentenced to 25 years in the slammer, passing away while incarcerated in 2016.
Victor Lustig: The Man Who Sold the Eiffel Tower—Twice
A scoundrel like Victor Lustig pulled many a con in his lifetime, but the bamboozle he is best known for is selling the whole-ass Eiffel Tower for scrap—twice! It all started in 1925 with an article debating whether the deteriorating Eiffel Tower should be repaired or sold. Lustig liked the sell, sell, sell option and liked it even more when he realized he could pretend to be the seller. He used a fake government ID to meet with several dealers, explaining the tower was too expensive to repair and needed to be hauled away by scrappers.
One dealer, André Poisson, handed Lustig a big fat check for all that wrought iron. Lustig, of course, cashed the check and disappeared. By the time Poisson realized what happened, he was too embarrassed to make a report to the police. Emboldened by the fact that he got away with it, Lustig went back to Paris and tried the same scam a second time. This time, the investor smelled something rotten and reported Lustig. He fled to America, where he graduated to counterfeiting and was eventually arrested for his efforts.
David Hampton: The Fake Poitier
When you’re the first black actor to win the Academy Award for Best Actor, you can almost guarantee there are going to be admirers and imitators. In the 1980s, David Hampton figured out a way to make a few bucks from the sincerest form of flattery. Hampton was able to con wealthy New Yorkers out of thousands by gaining their trust and convincing them he was the son of actor and director Sidney Poitier.
It seems the desire to be around famous people overpowered the desire to do any background checking because Hampton successfully gallivanted around town, obtaining free meals and plenty of cash. Although he was eventually arrested and served 21 months in prison, his story inspired the play Six Degrees of Separation by John Guare and, by extension, Six Degrees of Kevin Bacon. Although the movie version starred Will Smith, Hampton tried one more get-rich-quick scheme, suing Guare for $100 million, but just like all his other grifts, it failed.
Christophe Rocancourt: The Many-Faced Con Man
If you’re going to try your hand at a con, it’s probably a good idea to stick to just one story to keep things simple. Someone should have told that to Christophe Rocancourt, who began his scamming career in France. He posed as a nobleman and faked the deed to a property he didn’t own, selling it for a cool $1.4 million.
That should have been enough to hang up the con man's uniform for good, but Rocancourt had to go and complicate things. He came to the US in 1991, posing as a movie producer, an ex-boxing champion, and, if that wasn’t enough, he also claimed he was a relative of not only the Rockefeller family but also Sophia Loren. Rocancourt was finally fined $9 million for his crimes and ordered to pay his victims $1.2 million in restitution. After he was released from prison, things didn’t change much. He still hung out with celebrities in France and was eventually arrested again in 2014 for selling fake visas and passports.