The Big Question

What is the greatest scam of all time?

Graham Roumieu

Mark Seal, contributing editor, Vanity Fair, and author, The Man in the Rockefeller Suit

Ponzi. Madoff. The shysters who sold the Mona Lisa and the Brooklyn Bridge. All bow to this: 1626. A letter from New York. Purchased the Island Manhattes from the Indians for the value of 60 guilders,” wrote a Dutch merchant, referring to the 22,000 acres now called Manhattan. The price? Roughly $25. Suckers? Wait! Some say the tribe didn’t even own the island. Reverse switch. Gotcha. The long con always wins.

John Steele Gordon, business and economic historian

In the early 1700s, John Law, a Scottish financier, finagled his way to becoming the French equivalent of chairman of the Fed, secretary of the Treasury, and trade representative. He ran the stock of the Mississippi Company from 500 to 15,000 livres before it all crashed, ruining thousands, and he fled. The “Mississippi Bubble” crippled French royal finances for the rest of the ancien régime.

Robert Whitaker, author, Anatomy of an Epidemic

During the 1920s, John R. Brinkley harnessed the power of radio to tout an amazing new surgery for restoring a man’s virility: the placing of goat gonads into the testicular sac. He charged $750 for the 15-minute operation, which brought thousands of men to his office in tiny Milford, Kansas.

Michael Lewis, author, Flash Boys

God knows the biggest, but my favorite is Richard Whitney’s. The trusted head of the New York Stock Exchange and the face of American finance in the late 1920s and early 1930s, he ran his business and private life on loans he could never repay, from fellow financial elites who apparently never imagined they might be conned by one of their own. Whitney doesn’t even seem to have been all that clever. He just became so important to the financial system that the system couldn’t afford not to trust him.

Apollo Robbins, gentleman thief

In the 1930s, the De Beers diamond cartel sold the idea that a diamond engagement ring should be the iconic symbol of true love. A great scam requires you to sell the impossible while leaving the mark feeling warm and fuzzy.

Katherine Eban, investigative reporter, Fortune

In the 1980s, the Bank of Credit and Commerce International redefined full-service banking. It allowed terrorists and drug traffickers to hide their assets, and allegedly financed assassinations and arms purchases, including the CIA’s arming of the Nicaraguan Contras. Meanwhile, its “special duties” department falsified paper trails. To investigators, it became known as the Bank of Crooks and Criminals.

Matt Taibbi, journalist, First Look Media

Dreamed up in the ’90s by Russian gangster-pols and their Western advisers, the privatization “auctions” of the loans-for-shares scheme were actually crudely rigged pantomimes in which cronies of Boris Yeltsin were handed some of the world’s largest energy companies—like Yukos and Sibneft—for pennies on the dollar, instantly creating an oligarch class.

Criss Angel, magician

Training in magic allowed Harry Houdini to expose so-called psychics and mediums, who had successfully fooled many scientists and academics. He also served on a committee that offered a cash prize—never collected—to anyone who could demonstrate supernatural abilities. (He kept an open mind, telling his wife that if he were able to communicate posthumously, he would send her the message “Believe.” She held séances for 10 years after his death.) Earlier this year, I offered $1 million of my own in a challenge to a Long Island psychic. She declined.

Frank Abagnale Jr., security consultant and author, Catch Me If You Can

Bitcoin will make you the target of hackers who will steal your money. More expensive than other forms of payment, Bitcoin is a way to rob people of their life savings. Most important, if something goes wrong, the money may never be recovered.