Before Bernie Madoff
America’s story has always had a shadowy side. Long before Wall Street scandals and billion-dollar Ponzi schemes, there were gunslinging outlaws and silver-tongued schemers carving out their own twisted version of the American Dream.
It’s no surprise that figures like Bernie Madoff became household names—but dig a little deeper, and you’ll find that he was just one in a long line of con artists whose stories are every bit as jaw-dropping.
Charles Ponzi Gave His Name
While the first known cases of fraud go back to 300 BC, it was Charles Ponzi who caught the attention of the world. What started as a simple form of arbitrage—buying discounted postal coupons in other parts of the world and redeeming them in the US—eventually became his namesake crime.
Alexander Hamilton Even Got In Trouble
The subject of everyone’s favorite musical found himself in hot water when he was accused of financial corruption in 1797—and the reason why was scandalous. He’d conducted a brief but passionate affair years earlier, and the woman’s husband had blackmailed him to hide his dirty little secret. So while the accusations of financial corruption were true, Hamilton was also a victim of extortion.
John Trumbull, Wikimedia Commons
The Original Elizabeth Holmes
Long before Elizabeth Holmes and Theranos, there was Geraldine Elizabeth “Liz” Carmichael and the Twentieth Century Motor Car Corporation. Their signature vehicle, the “Dale,” had three wheels and a fantastical design. But not only was the car never produced, Carmichael ran off with investors’ money.
Colin Dangaard, Wikimedia Commons
Inigo Philbrick Was An Art World Darling
Inigo Philbrick was once a rising star in the art world—a sharp-suited dealer with a glittering roster of contemporary artists and an eye for turning canvases into cash. But behind the gallery walls, he was playing a far riskier game. Borrowing sleights of hand from the finance world, he sold more than 100% ownership in prized artworks, forged documents to drive up value, and secretly sold pieces that didn’t even belong to him. When the illusion finally shattered, the price was steep: a $86.7 million reckoning and a seven-year sentence
Patrick McMullan, Getty Images
The Walmart Wrongdoer
Tom Coughlin worked his way up the ladder at Walmart from the security division and made it all the way to executive vice president and vice chairman—only to experience a brutal fall from grace for misuse of company gift cards. Coughlin claimed he used the funds as bribes to prevent unionization at Walmart stores.
The Notorious H.H. Holmes
He was one of the most prolific serial killers in history—and he was also a notorious fraudster. Aside from, ahem, the more horrific charges against him, Holmes was also accused of insurance fraud, forgery, swindling, three to four bigamous marriages, and horse theft throughout the years. Busy guy!
The Woman Who Went After Wendy’s
In March of 2005, a woman named Anna Ayala came forward and made a shocking claim: She said that she’d found a severed human finger in her chili at Wendy’s and that she planned to sue. Investigators moved quickly and found that there was no evidence the finger came from Wendy’s. The chain claims they lost $21 million in revenue due to the story, and ultimately Ayala was charged with attempted grand larceny.
The Love Story That Never Happened
Herman Rosenblat’s tale was almost too perfect to question—a heartbreaking love story born in the horrors of Buchenwald. As he told it, he was a starving boy in the concentration camp when a girl began tossing him apples over the fence. Years later, by sheer chance, they met again in New York. He recognized her instantly, proposed on the spot, and the world swooned. A multi-million dollar book deal followed, and even Oprah called it the greatest love story she’d ever heard.
But the truth unraveled just before publication. His wife had never lived near the camp. And at Buchenwald, no prisoners were ever allowed near the fence. The story that had inspired millions? Entirely fabricated.
Unknown Author, Wikimedia Commons
Operation Crystal Ball
For years, Rosa Marks and her family convinced scores of “clients” that they were not only psychic—but that they were in direct communication with the Archangel Michael. The Marks family made millions of dollars off their clients, including author Jude Devereaux. A federal investigation dubbed Operation Crystal Ball eventually resulted in 61 counts ranging from money laundering to wire fraud.
Embajada, CC BY 2.0, Wikimedia Commons
The Mugging Hoax
Ashley Todd was volunteering for the presidential campaign of Senator John McCain when she alleged that she’d been mugged and beat up by supporters of his opponent, Barack Obama. With just two weeks until the election, it seemed like a class “October Surprise”—but then, police poked holes in her story, and Todd confessed that she’d made it all up.
Gage Skidmore, CC BY-SA 2.0, Wikimedia Commons
The Kentucky Barracuda
Parker Hardin French’s adventures in the 19th century were the stuff of legend. His stories always seemed too wild to believe—and in many cases, they were. Beyond the tall tales, there was also a rich history of borrowing money only to disappear. That’s how this con man got the nickname “The Kentucky Barracuda”.
The “Wizard”
The American preacher Roy Elonzo Davis was one of the co-founders of the second version of the Ku Klux Klan—but that’s just the tip of the iceberg when it comes to Davis. He was charged at various times with counts of fraud, grand theft, petty theft, forgery, illegal firearms possession, trafficking, cross burning, and libel.
Unknown Author, Wikimedia Commons
The “Thoughtographer”
Theodore Judd Serios was just a Chicago bellhop—until he claimed he could do the impossible. With nothing but a camera and intense concentration, he said, he could project images from his mind directly onto film. He called them “thoughtographs,” and for a brief, bizarre moment, the world listened. Scientists, psychics, and photographers lined up to witness the phenomenon. But as the flashes faded and the photos developed, so did his credibility. To skeptics, Serios was less psychic visionary and more sleight-of-hand showman—his strange gift likely nothing more than a well-timed trick.
Jule Eisenbud, Wikimedia Commons
Big Eyes
Walter Stanley Keane’s lies were not only exposed by his ex-wife—she did it in an utterly humiliating way. Keane had taken credit for his wife Margaret’s paintings of wide-eyed subjects for years. Finally, they ended up in court, where the judge asked them each to produce a painting in that signature style. Walter demurred—and Margaret completed one in 53 minutes.
The Baron Of Arizona
In the late 19th century, James Addison Reavis tried to make a fraudulent land claim for the Peralta land grant (AKA the Barony of Arizona). It would’ve landed him 18,600 square miles—to say nothing of the of the millions of dollars in claims he began selling. When his claim was rejected, he tried to sue the government—who then exposed his fraud and threw him behind bars.
Unknown Author, Wikimedia Commons
The Spiritualist
People in the US and abroad were absolutely obsessed with spiritualism and all that it entailed—seances, mediums, spirit photography included—in the 1800s. Of course, many fraudsters took advantage of this, including Leonora Piper, who used cold reading, muscle reading, and fishing to fool her clients, who had her handsomely for her services.
Internet Archive Book Images, Flickr
The Real Doctor Frankenstein
Stephen Douglas Gore operated under the guise of a body donation business—but what he was really running was something far more disturbing. He preyed on grieving families, forging documents or coercing consent to obtain the remains of their loved ones. What he did next defied both ethics and imagination. In one grotesque case, he even sewed a severed head onto a different body. It was a horror show masquerading as science—and yet, despite the unspeakable violations, Gore received just a single year behind bars.
The Original Catfish
Before “Catfish,” there were “Lonely Hearts Scams,” which often took place through the mail and in classified ads. One prolific fraudster in this arena was Susanna Mildred Hill, a 60-year-old woman who pretended to be much younger in order to get men to write to her and send gifts throughout the 1940s.
The Hollywood Fraudster
David Begelman was a successful Hollywood producer, executive, and talent agent who worked with stars like Judy Garland and Fred Astraire—but the whole time, he was padding his pockets. Begelman forged checks from his employer, Columbia Pictures, for upwards of $75,000. Strangely, Columbia initiaully refused to acknowledge it and even fired a CEO who tried to oust him—only to eventually get rid of him anyway.
Doctor Death
Richard Pryde Boggs was a prominent California neurologist who ended up playing a key role in a disturbing scheme. It involved taking the life of one man and then forging identification documents to give him the identity of another man, leading to a $1.5 million insurance payout. He was exposed when the insurance company began an investigation.
Spy Vs Spy
Wayne Simmons made a name for himself as a fiery Fox News commentator, boasting a shadowy past as a former CIA operative. He spoke with authority, swagger, and just enough mystery to make people listen. But there’s one group that doesn’t take kindly to stolen valor: real CIA veterans. When they looked into Simmons’ story, the truth unraveled fast. He’d never served a day with the agency. And the lies didn’t stop there—he was also convicted of defrauding a woman out of $125,000. His greatest operation turned out to be a con.
Jim.henderson, Wikimedia Commons
The Quack
The world of medical patents is a surprisingly cutthroat and profitable one. Ellisha Perkins was the creator of what he called Perkins Patent Tractors in the 18th century, and he claimed they curated inflammation and rheumatism. He said the strange rods were made of a propriety metal alloy—but it’s generally believed that any claims of the device’s efficacy are due to a placebo effect.
Geni, CC BY-SA 4.0, Wikimedia Commons
The Queen Of Nowhere
How do you deal with pesky American fraud laws? Invent your own country, of course. That’s what Pearlasia Gamboa did when she made herself president of the micronation the Dominion of Melchizedek, which exists in cyberspace. Despite her efforts, she’s successfully been sued by the US Securities and Exchange Commission.
America’s Prophet
What is it about those new age types and fraud? Sean David Morton, who calls himself “America’s Prophet,” claims to be a psychic, a ufologist, and have remote viewing powers and has used these purported powers to bilk investors. Not only has the SEC said he’s a scammer, he’s also been pursued by the Federal Government for tax fraud.
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