5 of History's Most Cunning Con Artists

By: Dave Roos  | 
Julia Garner, "Inventing Anna."
Julia Garner stars as Anna Delvey (Sorokin) in the Netflix miniseries "Inventing Anna." Netflix

The original "Confidence Man" was a charming crook from the 1840s named William Thompson. His "con" was to strike up a conversation with a stranger, win their trust and then ask an odd question: Did they have enough confidence in him to lend them their gold watch for the day? Yes, people actually fell for that.

And times haven't changed much. It's amazing how far some people go to con their unsuspecting friends as well as strangers. Here are five more cunning con men (and women).


1. Charles Ponzi and His Infamous 'Scheme'

You know you're an accomplished con man when they name an entire crime after you. In the 1920s, Charles Ponzi duped investors out of an estimated $32 million (around $475 million today) using the infamous "scheme" that now bears his name.

A Ponzi scheme starts with a too-good-to-be-true investment opportunity. In Ponzi's case, he guaranteed to double his investors' money in just three months by buying and selling "international reply coupons," a way to prepay foreign postage on international mail. The details were sketchy, but Ponzi's early investors struck it rich just like he promised.


That's why Ponzi schemes are able to fool so many otherwise smart people. They appear to be hugely profitable. The problem with Ponzi's scheme — and later iterations like Bernie Madoff's record-breaking investment fraud — is that the money is never invested in an actual security. Ponzi and Madoff simply took the flood of money coming in and paid it back to the early investors (and themselves, of course).

Charles Ponzi
Financial swindler Charles Ponzi looks charming in this 1920 photograph.
Walter Gircke/ullstein bild via Getty Images

At one point, Ponzi was receiving $1 million a week from eager Americans banking their futures on his incredible investment opportunity. When The Boston Post exposed Ponzi's con, he was thrown in prison and his investors lost their homes and life savings. Less than a century later, Madoff "made off" with $19 billion before his Ponzi scheme collapsed.


2. Anna Delvey, the 'SoHo Scammer'

From 2013 to 2017, it seemed like Anna Delvey was everywhere — European art exhibitions, exclusive New York nightclubs, $4,000-a-night hotels — and was "close friends" with everyone from famous actors to tech moguls to trust-fund fashionistas. With her vaguely European accent, haute-couture clothing and a habit for tipping with crisp $100 bills, everybody assumed she came from money.

So, when Delvey's credit card was declined at fancy restaurants, or the airline wouldn't let her pay in cash for those first-class tickets to Morocco, she'd ask one of her new friends to cover the expense. She'd pay them back, of course. But she never did, and they were too embarrassed to bring it up.


Delvey's schemes began to unravel in 2017 when she was kicked out of multiple New York City hotels and restaurants for failure to pay, and appeared in a New York Post article under the headline "Wannabe socialite busted for skipping out on pricey hotel bills."

Delvey's real name is Anna Sorokin, a Russian-born German citizen who successfully conned her way into the inner circles of the fabulously rich, young and gullible. Until she was caught. Sorokin served more than three years in prison and currently remains in U.S. immigration custody. She is the subject of Netflix's fictionalized drama "Inventing Anna."


3. Natwarlal, the 'King of Cons'

India's most notorious and celebrated con man has been credited with "selling" the Taj Mahal to clueless tourists, forging the signature of Indian President Rajendra Prasad, and escaping from prison at least eight times, including once in a guard's uniform. Born Mithilesh Kumar Srivastava, India's "king of cons" was better known as Natwarlal.

Natwarlal was a gifted forger and actor. One of his favorite cons was to pose as a personal assistant to a dignitary or politician and enter a jewelry store, placing a large order for expensive watches to be presented in a special government ceremony. When it came time to pay for the watches, Natwarlal would arrive in a chauffeured car and drive the jewelry store clerk to a bank, where Natwarlal would emerge with a perfectly forged cashier's check for the full amount. By the time the check bounced, Natwarlal was long gone.


Natwarlal boasted that no prison could hold him for more than a year, and that wasn't an exaggeration. He was sentenced to 113 years behind bars for dozens of scams, but only served 20 of them. His most brazen escape came in 1957 when he broke out of the Kanpur jail in a smuggled guard's uniform and paid off the guards with a suitcase filled with cash that turned out to be old newspapers. Another time he faked a kidney ailment in police custody and persuaded his captor to take him to a posh hotel where he allegedly staying, so he could get money to pay the doctor. At the hotel, he gave his captors the slip.

In India, a particularly gifted swindler is called a "Natwarlal" in honor of the legendary thief, who was also the inspiration behind the 1979 Bollywood thriller "Mr. Natwarlal." He died either in 1996 or 2009, depending on whether you believe his brother or his lawyer. Even in death, the con continued.


4. Simon Leviev, the 'Tinder Swindler'

On the popular dating app Tinder, all it takes is a single "swipe right" to spark a connection with a complete stranger. It's also the perfect place for a con man to find his next mark. For years, Simon Leviev charmed a series of successful and beautiful European women into trusting him and even loving him, and then allegedly duped them out of an estimated $10 million.

When Leviev went on dates, he presented himself as the heir to an Israeli diamond-industry fortune and he seemed to have the money to back it up. He'd fly his new girlfriends around on his private jet and treat them to lavish meals and stays at four-star hotels. What they didn't know was that all of it was being paid for by the last woman who fell for his fraud.


Once the relationship was getting serious, Leviev would reveal that his life was in danger and he needed to send money from a third-party account so it couldn't be tracked. The worried girlfriends complied, charging tens of thousands of dollars to their credit cards, or even sending him a suitcase of cash. Leviev would soon disappear, using the swindled money to fund his next con.

Tinder Swindler" Shimon Hayut
"Tinder Swindler" Shimon Hayut(L), aka Simon Leviev, was arrested and deported from Greece in 2019 after reports surfaced that he had defrauded many women.

Leviev ( whose real name is Shimon Hayut) served just five months for similar schemes committed in Israel, but he's evaded criminal charges so far for his European cons. As of this writing, he's a free man and is considering a career move to Hollywood. His con was also the subject of a Netflix documentary.


5. Gregor MacGregor, the Scottish Financier Who Invented a Country

In the early 19th century, European investors were looking for new places to park their money, and Latin America looked very attractive. With the fall of the Spanish Empire, there were a slew of new, independent countries in Latin America eager to attract investors in their growing economies, and their debt paid better than European bonds. If you could stomach the risk, Mexican bonds paid 6 percent, for example.

Enter Gregor MacGregor, a Scottish financial schemer who would have made Bernie Madoff blush. With so much excitement over Latin American investment, MacGregor decided to invent his own Latin American country called Poyais on the coast of Honduras. Not only did MacGregor convince hundreds of investors to buy Poyais government bonds, but dozens of Scottish families actually boarded ships and emigrated to this made-up nation!


It didn't go well. Instead of finding friendly natives and fertile soil, the settlers found malaria and malnutrition. Two-thirds of the original 250 Scottish settlers died and the British Navy was deployed to turn back more ships that had set sail for MacGregor's promised land. Undeterred, MacGregor tried the same con again in France, but they threw him in jail.

All told, MacGregor raised £1.3 million selling fake government bonds, which is worth roughly $5 billion today. Pursued by angry investors, he died in exile in Venezuela.