25 Greatest Cons In Human History

Lou Pearlman is famous for bringing NSYNC and the Backstreet Boys to fame. Then he used his fame to dupe investors in a massive Ponzi scheme.

Convinced of his credentials because of the successful bands, people invested in Pearlman’s other businesses which he claimed included an airline, despite that being a total lie. He took out $190 million in bank loans and mixed the money together, paying whoever needed money whenever they needed it from either source. He fled to Bali but was eventually caught and sentenced to 25 years. 

Ever heard someone make a joke about selling you the Brooklyn Bridge? Thank George Parker for that one. In the 1880s, Parker would find visitors to New York who seemed a little naïve, and he’d convince them he owned the bridge. He convinced his marks they could make a fortune charging a toll and then sold them the bridge. He made at least $50,000 and he did it more than once.

James McCormick ended up getting 10 years in jail for one of the most brazen and also dangerous cons of all time. He made £50 million selling around 7,000 fake bomb detectors to different countries. His machines, which were really just golf ball finders, were set up all through Iraq at checkpoints between 2008 and 2010. No one knows how many people died as a result of the useless machines. 

If a con leads to an entire revolution, that’s a hell of a con. The Affair of the Diamond Necklace involved Jeanne de Valois-Saint-Rémy, a fraudulent French Countess. She convinced a Cardinal to buy an extremely expensive diamond necklace after convincing him it was for the Queen. The fake countess sold the necklace and when the fraud was finally exposed, the French people had finally had enough of their government being a useless autocracy and soon came the French Revolution. 

It’s hard to scam people when you’re in the spotlight, but Milli Vanilli pulled off a hell of a con on the world stage and even won a Grammy doing it. The pop duo was huge in the 80s, sold nearly 9 million albums, and performed for stadiums. Turns out neither of them could sing. They were hired to dance and lip sync, to be the faces of the song, and they readily obliged. 

When news broke that they hadn’t sung a word of their music, they returned their Grammy and basically lost their careers.

Okay, so maybe this isn’t the “greatest” con, but it involves too many insane details to ignore. Famous artist Salvador Dali once conned Yoko Ono out of $10,000. She wanted his mustache hair for some reason and, afraid Ono was a witch, he didn’t want to oblige. But he still took her money and sent her a dry blade of grass from his yard in a nice box.

Not every con is about stealing money. L.W. Wright conned his way into a NASCAR race despite having no experience driving. He got into the Talladega 500 in 1982 after convincing people he’d had 43 starts in another series and was sponsored by Waylon Jennings. Despite numerous holes in his story, he managed to get ahold of a car and then borrow someone else’s crew. He crashed in his 2nd lap of qualifying then was parked for not maintaining speed. And then he just vanished, never to be seen again.

Van Brink managed to start his own bank in Grenada using a fake $20 million ruby as collateral. Thousands of investors put their money into the fraudulent bank, giving Brink access to $170 million. Like many scams, it was run as a Ponzi scheme so early investors, promised great returns on their investment, got checks back. Meanwhile, Brink was buying houses, vacations and a yacht. Brink was charged with fraud but died of a heart attack before prosecution.

William Mead came up with a con to coincide with the arrival of Halley’s Comet. He set up a fake meeting with a real contractor. At the meeting they would “discover” a wallet. The paperwork inside would indicate it was owned by a stadium developer.

Mead and the mark would meet the developer, who was Mead’s accomplice. They’d convince the mark that he could lease the developer’s stadiums for viewers to see Halley’s Comet. The contractor would pay up to the tune of $10,000. Mead managed to pull this con off a number of times before the comet finally came and went.

Con man is short for confidence man and William Thompson is the reason the term exists at all. A clean cut, well-dressed fellow, he would approach a stranger on the street and strike up a conversation. You know those people who can talk to anyone about anything? That was Thompson. At some point he would say to this total stranger “do you have the confidence to trust me with your watch over night?” And, very often, the mark would agree. They’d hand over the watch and he’d just leave.

Making diamonds is not easy. Coal, which is carbonized plant matter, doesn’t really turn into diamonds. But that myth is so persistent it allowed Henri Lemoine to dupe the team who ran De Beers diamonds back in 1905.

Lemoine mixed his “secret chemical formula” with coal and then put it in a furnace. When he pulled it out, diamonds were there! He’d just done some sleight-of-hand switcheroo, but the De Beers team were convinced. Investors lined up, and it’s estimated Lemoine got as much as 1.5 million francs before he was found out.

Anthony Gignac convinced people he was Saudi royalty and scammed his way to $8 million. His scams involved duping other wealthy people to invest in things he claimed to be backing. Convinced he had a massive personal fortune, others readily agreed, and he made off with their investments.

Gignac was finally found out when, working on a hotel investment scam, the hotel owner he was trying to rip off saw him eating pork which a Muslim would not do. He got 19 years in prison for his many schemes.

Born in 1743, Cagliostro made a name for himself with schemes often based around the mystical and paranormal. He once scammed a goldsmith by promising to lead him to a secret cave of riches only to have the man run off by “demons,” disguised goatherds Cagliostro had previously hired.

He would go on to tour Europe claiming to know mystical and alchemical secrets. He sold love potions and other elixirs that did nothing but kept him living a rich and lavish lifestyle for years. He continued running scams and forging documents for over 10 years.

Lord Gordon Gordon kept his real name a secret. He pretended to be a nobleman and convinced people he had an interest in America’s new rail system. Believing him to be a wealthy European investor, railroad officials spent tens of thousands of dollars schmoozing him, convinced he had millions to invest. He did not. 

In New York, Jay Gould gave Gordon $1 million in stock and $200,000 in cash to take over the operation. This was 1872. That’s over $29 million today. After being found out he fled to Canada and eventually took his own life.

They called Joseph Weil America’s Greatest Conman and his career lasted half a century. It’s said he scammed thousands of people out of close to $8 million. Two million of that came from Italian dictator Benito Mussolini. A showman by nature, he even wrote an autobiography explaining his many cons and justifying it all by claiming his victims all wanted to get something for nothing so he gave them nothing for something.

Theranos was going to change the world of blood tests. One finger prick and up to 30 tests could be conducted in mere hours. Founder Elizabeth Holmes sold it as a game changer. The company was valued at $9 billion and got $700 million in investments. Turns out, the company was a scam. Their machines didn’t work. Holmes was just a con artist. She ended up getting 11 years in prison.

Carlos Kaiser managed to spend over a decade as a professional footballer despite never playing a game and really having very little skill at the game. His scam was just to charm everyone he could. He’d talk up his own skills to everyone everywhere until everyone had heard of him and how great he was, even if no one had seen him play. That got him signed to team after team and, when he had to play he’d fake an injury and eventually get traded elsewhere.

Few con men are more well known than Frank Abagnale, thanks to Leonardo DiCaprio playing him in the movie “Catch Me If You Can.” Abagnale had a knack for being a chameleon and started his scams at the age of 15. He was caught and imprisoned in multiple countries but he kept going, escaping from prison at one point and also committing various forgeries and impersonations. Ironically, his biggest con seems to be his life story as depicted in the film, much of which has turned out to be fake.

One of the most famous cons in recent years, the Tinder Swindler was the nickname of Simon Leviev (just his most well-known alias). His elaborate cons were essentially a $10 million Ponzi scheme across Europe. He would meet women on Tinder, pretend to be a rich businessman and eventually claim he needed help because people were “after him” or some other excuse. He would pay older victims back with money from new victims to keep the fraud going.

Sam Israel III was a hedge fund manager who raised $450 million for his fund which turned out to be a Ponzi scheme. To cover his fraud, he even founded a fake accounting firm to audit the real company and assure clients all was well. After being sentenced to 20 years in prison, Israel tried to fake his own death to escape justice but got caught and earned two more years in jail.

Natwarlal has been called the greatest con man ever. His life story is riddled with legend and exaggeration so it’s hard to know for sure what’s true. It’s said he escaped from prison 10 times. But his biggest scheme involved pretending to be a government official and selling the Taj Mahal. Apparently he did this three times. 

He was a master forger and had at least 50 aliases. His final prison escape came in 1996 when he was 84. His brother said he died shortly thereafter, his lawyer said he died in 2009. Officially, no one knows when he died.

In 1822, Gregor MacGregor convinced people he was the prince of a land called Poyais. In reality, he was the son of a Scottish banker. He told of how Poyais had fertile land and an abundance of gold.  All MacGregor needed was investors to develop the land. He raised  £200,000 in cash and bonds worth over £1.3 million then filled seven ships with settlers.

They traveled to an empty corner of Honduras where no promised land awaited. Nearly two-thirds of the people died. MacGregor fled and never faced justice.

Victor Lustig sold the Eiffel Tower not once but twice. A Secret Service agent once told him he was the smoothest con man who ever lived. 

In the 1920s, Lustig pretended to be a French government official. He arranged to meet with scrap dealers and explained that the Eiffel Tower was going to be torn down. The scrappers bid on the job and Lustig took the money. It worked so well he did it a second time.

Bernie Madoff pulled off arguably the biggest scam ever. Over 20 years it’s believed Madoff managed to cost his investors over $50 billion. How did he do it? The biggest Ponzi scheme of all time. He promised big returns on investments, kept the money and then paid off old investors with money from new investors. Things only fell apart in 2008 when investors wanted to cash out for more than Madoff had available. The fact he kept it going for so long was remarkable in and of itself.

For his trouble, and the sheer size of his scam, Madoff got 150 years in jail. 

Charles Ponzi’s name is synonymous with cons. As we saw with Madoff, a Ponzi scheme is a simple but unsustainable con. You offer a big return on an investment and take people’s money. When it comes time to pay out, you pay early investors with money from later investors. You can sustain this for as long as you can trick new investors. After that, you better have an escape plan.

Ponzi pulled off his scam in the early 1900s and did well for quite a while. He made $15 million in 8 months, which would be $222 million today. Eventually he was caught and imprisoned before returning home to Italy. He died poor in Rio at age 67.