16 Real and Imaginary Con Artists Who Pull Off the Most Incredible Schemes

The Con Artist (also known as the swindler, scammer, or grifter) is a close cousin to the thief. While they don’t necessarily steal, it’s not below them to trick you into freely giving them what they want.

They’re able to trick their way in and out of any situation, from infiltrating exclusive events to getting away from justice.

Real-Life Con Artists

While con artists take up a fair amount of space in fiction, their nonfiction counterparts don’t fall behind in offering you the most unbelievable tricks and scams.

Below are some of these real-life con artists who have made it as history’s legendary swindlers. Some of their exploits you’ll find laughable, while others you’ll simply think are horrifying.

1. Elizabeth Holmes as told in Bad Blood by John Carreyrou

Theranos founder and CEO Elizabeth Holmes was widely considered the next Steve Jobs. Brilliant and charismatic, she promised the world a faster and easier way to test blood—something that would potentially revolutionize the medical industry.

There was just one problem: her technology didn’t work. That didn’t stop her and her business partner from keeping it quiet while raking in the money, though.

2. Charles Ponzi as told in Ponzi’s Scheme by Mitchell Zuckoff

Imagine having a scheme so associated with your identity that the world not only names it after you, but the majority of people only know you from it. That’s essentially Charles Ponzi’s legacy.

Sometime in the early 1920s, Ponzi started promising investors to double their money after only a mere three months. To fulfill that promise, he used the money taken from more recent investors to pay his old clients. The money ultimately came back to him because people kept re-investing in his scheme.

3. John R. Brinkley as told in Charlatan by Pope Brock

In 1917, John R. Brinkley began claiming that he had found the answer to male impotence: transplanting goat testicles onto humans. Surprisingly, a lot of people took him up on his offer. He later expanded his business to selling his own medicine and offering medical advice over the radio.

But he wasn’t even a doctor and his procedure wasn’t supported by any medical research. As a result, dozens of people died or were wrongfully diagnosed.

4. Leo Koretz as told in Empire of Deception by Dean Jobb

Leo Koretz operated much in the same way and almost at the same time as Charles Ponzi. But instead of using postal reply coupons, Koretz took advantage of fraudulent oil claims in Panama to lure his investors.

He was so trusted by his investors that after Ponzi’s arrest, they jokingly called him “Our Ponzi,” never realizing that they were being duped the same way. His scheme was only discovered when his wealthier investors traveled to Panama to take a look at fictional oil operations there.

5. The Enron Executives as told in The Smartest Guys in the Room by Bethany McLean and Peter Elkind

Energy company Enron was once the darling of the 90s corporate world. A rising star, it boasted consistent profits that reportedly came to at least $100 billion during the year 2000.

It was only when an article (by one of the book’s authors)questioned how the company made money did people take a closer look at the company. It turns out, their skyrocketing profits were a result of the company’s executives committing corporate fraud.

6. Joseph Weil as told in Conman by himself and W.T. Brannon

“Yellow Kid” Weil worked with many fellow con men and started a wide range of successful cons. During his career, he reportedly swindled more than $8 million from various people.

Some of his best-known schemes were tricking Benito Mussolini out of $2 million, selling oil-rich lands he didn’t own, and staging fake prizefights.

7. Edgar Laplante as told in King Con by Paul Willetts

Edgar Laplante was a small-time con man and actor who who decided to reinvent himself as Chief White Elk—war hero, civil rights leader, sportsman, and Cherokee nation leader.

Under this guise, he went around the American West and eventually Europe, duping world leaders, rich businessmen, and high-class women alike. At one point, he even went to Italy and posed as a delegation member for the League of Nations.

8. Catch Me If You Can by Frank W. Abagnale

Frank Abegnale tells his true story of how he became one of the world’s most sought-after con men, posing as a pilot, doctor, layer, and professor all before he was 21.

Known by the police of 26 countries and all 50 states as “The Skywayman,” he lived a luxurious life on the run until the law finally caught up with him.

Con Artists in Fiction

Literature tends to treat the con artist as being one of two extremes. They can be the lovable rogue who restricts their cons to the rich, the unlikable, and those who deserve it. Or perhaps they’re the total scoundrels who particularly like preying on the desperate, the vulnerable, and the gullible.

Below are a few examples of the literary con artists and the daring schemes they pull off. Some of them are complete villains, while others are more of the loveable sort.

Spoiler Alert! The tricks performed by the con artists below are significant to their narratives. Anything you read past this point may affect your reading experience with these books.

9. John Constantine from Hellblazer by Various Authors

John Constantine calls himself a magician, but most of his success lies in his talent for the con. His scams extend from gullible mortals to a plethora of supernatural beings.

In Dangerous Habits, he manages to sell his soul to three unsuspecting Lords of Hell. Each lord, too proud to cede their claim on him, ultimately decides to heal him and bring him back to the world.

10. The Wizard from The Wizard of Oz by L. Frank Baum

The Wizard of Oz is venerated by all of his subjects, who believe that he possesses potent magic. Thinking that he is the only one who can solve their problems, Dorothy and her crew journey to his palace for help.

It turns out that the wizard is just an ordinary man from Nebraska who accidentally sailed into the Land of Oz. He uses elaborate tricks and props to maintain the illusion of being “great and powerful.”

11. Loki and Odin from American Gods by Neil Gaiman

The story of American Gods is basically a two-man con. The Old Gods are losing power as people begin believing in a newer generation of gods.

Loki and Odin then scheme to have the Old and New Gods fight each other to the death, taking power from the resulting chaos. They even go as far as orchestrating the protagonist’s birth.

12. Tom Ripley from The Talented Mr. Ripley by Patricia Highsmith

Tom Ripley is a struggling man from New York City who keeps himself above water by doing whatever’s necessary. A chance encounter with someone leads him to Italy, where he first experiences a lavish life.

Desperate to hold on to his new life, he commits murder and assumes a different identity. Most of the novel then shifts to him maintaining the deception.

13. The Gentlemen Bastards from The Lies of Locke Lamora by Scott Lynch

To the thieves community, the Gentlemen Bastards are simple second-story men. But to the rich and powerful nobility of Camorr, they’re a force to be feared.

Trained by a gifted mentor, the Bastards know everything there is to tricking nobles out of their fortunes. At one point, they even trick their marks in two ways: as swindlers posing as merchants and the lawmen who eventually reveal the scam.

14. Moist von Lipwig from Going Postal by Terry Pratchett

When it comes to con artists, Moist von Lipwig checks every box. He’s smart, charming, and believes he’s above other criminals. After all, he does it for the challenge and never hurts anyone.

But then he’s captured and sentenced to death. It’s a good thing the government wants his criminal genius to solve a long-standing problem—organize the mail.

15. Dr. Vladimir Dragan from The Little Red Chairs Edna O’brien

Dr. Vladimir Dragan arrives at a little Irish village and sets up shop. From poetry to sex therapy, he does it all. Charming, pretty, and sophisticated, he quickly wins the villagers over.

Then he’s arrested and revealed as the notorious Beast of Bosnia—a war criminal whose crimes include genocide, torture, and ethnic cleansing.

16. The Soldiers from The Stone Soup by Marcia Brown

It’s odd that a beloved folktale often told to children encourages us to cheer for the con artist. In this story, a group of hungry strangers resort to tricking a whole village into creating a delicious meal.

The details change from place to place, but this particular version sees tired soldiers setting up a cauldron and claiming to cook a “stone soup” fit for royalty. The initially selfish villagers, curious about how it tastes, begin contributing food to the soup to make it better. They eventually give enough to create a tasty meal.

What Is a Con Artist?

Con artists are called so because they first gain your trust—your confidence—before exploiting you for all that you have. They prey on people who are easily manipulated, mainly those who are naive, egotistical, irresponsible, or greedy.

The basic con artist is seen on the streets, operating simple confidence scams that are interesting enough to draw in victims, but seem harmless enough to evade too much attention.

For example, a man offering a prize for correctly guessing which cup a coin is in seems like an easy way to make money. What the people don’t know though, is that the contest is rigged. The only person who stands to get rich is the con artist.

As the con becomes more complicated, so do the risks and rewards. From targeting high-profile people to entire organizations, con artists not only live for whatever they can take, but also for the excitement of the con.