February 23, 2024 | Samantha Henman

America’s 25 Most Notorious Fraudsters


Bernie Madoff Was The Biggest

From Wild West outlaws to the robber barons of the Gilded Age, it seems like America as we know it was built on fraudsters. Perhaps none are as notorious as Bernie Madoff, who operated history’s largest Ponzi scheme—but they all have stories that are just as compelling, if not more.

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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.

Portrait Photo of Charles Ponzi  swindler and con artist who operated in the U.S. and Canada.Jared Enos, Flickr

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.

Portrait Painting of Alexander Hamilton by John TrumbullJohn 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.

Elizabeth Carmichael With Model Of The Dale AutomobileColin Dangaard, Wikimedia Commons

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Inigo Philbrick Was An Art World Darling

Inigo Philbrick represented prominent artists as an art dealer and gallerist—but he borrowed tactics from the financial world, like selling shares in certain works of art that totaled over 100%, falsifying documents to inflate value, and selling artworks without the knowledge fo their owners. His punishment? $86.7 million and a 7-year sentence.

Inigo Philbrick attends Huntsman on 57th Celebration Dinner at Le BernardinPatrick 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.

Walmart store exterior In 2008Walmart, Flickr

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!

Grayscale Photo of H. H. Holmes, America's first serial killer.Cape May MAC, Flickr

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.

Anna Ayala, the woman who was arrested after claiming she bit into a human finger in a bowl of Wendy's chili.Handout, Getty Images

The Love Story That Never Happened

Herman Rosenblat was a Holocaust survivor who claimed that he’d first met his wife when he was a child at the Buchenwald concentration camp, where she’d smuggled him food. They reunited years later in the US and when he recognized her, he’d proposed. He was offered a multi-million dollar book deal, only for his lie to be revealed before publication.

His wife had never lived in the neighboring town, and while he’d been at Buchenwald, prisoners weren’t allowed to approach the fence.

Portrait Photo of Herman A. Rosenblat (c. 1929 – February 5, 2015)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.

Portrait Photo of Jude Deveraux an American author of historical romancesEmbajada, CC BY 2.0, Wikimedia Commons

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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.

Portrait Photo of U.S. Senator John McCain speaking with supporters at a campaign rallyGage 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”.

Woodcut from an ambrotype photograph of Parker H. FrenchS.F. Baker, Wikimedia Commons

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.

Grayscale Portrait Photo of Roy Elonzo Davis (1890-1966)Unknown Author, Wikimedia Commons

The “Thoughographer”

Theodore Judd Serios was a bellhop at a Chicago hotel who made a seriously bizarre claim. He said that he could put images on film using only his mind—what he called “thoughtographs”. It was a strange case, even in the world of psychic phenomena. Both skeptics and professional photographers claimed that Serios was anything but serious about his claims.

Grayscale Photo of Ted Serios, a Chicago bellhopJule 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.

Screenshot from the movie Big Eyes (2014)Tim Burton, Big Eyes (2014)

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.

Grayscale Portrait Photo of James Addison Peralta-ReavisUnknown Author, Wikimedia Commons

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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.

Grayscale Photo of Leonora E. Piper wearing black outfitInternet Archive Book Images, Flickr

The Real Doctor Frankenstein

Stephen Douglas Gore performed the unthinkable—he not only manipulated people who’d lost family members, he either coerced them or forged documents to obtain their loved ones’ corpses, and then did obscene things to the bodies, including one instance where he sewed a head on another body. Incredibly, he was only sentenced to a year in jail.

Screenshot from the movie Frankenstein (1931)Insomnia Cured Here, Flickr

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.

Gift wrapped in blue paperSuzy Hazelwood, Pexels

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.

David Begelman, shown in 1976 file photo, central figure in a financial scandal involving misuse of funds, resigned 2/6 as president of Columiba PicturesBettmann, Getty Images

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.

Close-up Photo of US PassportDaniel Foster, Flickr

Spy Vs Spy

Wayne Simmons was a frequent Fox News guest with a compelling history: He claimed to be a former CIA agent. Well, if you can count on one group who’d be both willing and able to expose stolen valor, it’s other CIA personnel—and that’s exactly what they did. It turns out he was not only lying about his past, and he also got convicted of defrauding a woman for $125,000.

Fox News building on a snowy afternoon.Jim.henderson, Wikimedia Commons

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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.

Photo of modern copies of Perkins tractors in the science museumGeni, 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.

Malpelo Oceanic Island of ColombiaCAUT, Flickr

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.

Human hands near a flashing ballhidesy, Shutterstock

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