America’s 25 Most Notorious Fraudsters

Bernie Madoff Was The Biggest

From Wild West outlaws to therobberbarons 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.

Charles Ponzi Gave His Name

While the first known cases offraudgo 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 Trumbull

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.

Elizabeth Carmichael With Model Of The Dale Automobile

Colin Dangaard, Wikimedia Commons

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 Bernardin

Patrick McMullan, Getty Images