History’s Greatest Con Artists: The Confidence Men

A gallery of history's great swindlers — and the matching vanity in their victims that made every con possible.

A con is the only crime that requires the victim's active participation. The pickpocket needs nothing from you; the confidence man needs your cooperation, your signature, and above all your belief that you, specifically, are clever enough to be on the winning side of something too good to be true. Every figure below was a virtuoso of human vanity — but note, in each, the second mark: the one who handed over the money not in spite of his shrewdness but because of it. The blade cuts both ways here, at the swindler and at the greed he rented.

The Man Who Sold the Eiffel Tower — Victor Lustig, 1925

Lustig forged government stationery, gathered scrap-metal dealers in a Paris hotel, and confidentially explained that the city, unable to afford the Eiffel Tower's upkeep, was quietly selling it for scrap. A dealer paid him a fortune for the rights. It worked so well that Lustig came back and sold the tower a second time. The legend has him conning Al Capone personally and living to tell it.

The verdict: He understood the one thing every great swindler knows: that a man told a secret will stop checking the facts, because the secret has already flattered him into an accomplice.

The Original Scheme — Charles Ponzi, 1920

Ponzi promised investors fifty percent returns in ninety days, paid the early ones with the money of the later ones, and watched a tide of cash roll in from people certain they had found the one machine that prints money. It collapsed, as it mathematically must, the instant new fools ran short — but not before he had lent his name permanently to the structure itself.

The verdict: The scheme that bears his name has been understood, explained, and outlawed for a century, and it will take in someone new before the end of this sentence.

“And If You Believe That, I Have a Bridge to Sell You” — George C. Parker, c. 1900

Parker repeatedly “sold” the Brooklyn Bridge to newly arrived immigrants, complete with forged deeds, persuading buyers they could set up toll booths on it. The story has it that police periodically had to remove confused new owners attempting to take possession of a public bridge. He sold landmarks he did not own so often that he wrote the idiom into the language.

The verdict: The buyers' fatal question was never “does he own it?” but “how soon can I start charging everyone else?” — and the greed answered before the sense could.

The Country That Did Not Exist — Gregor MacGregor, 1820s

MacGregor returned to Britain claiming to be the ruling prince of Poyais, a thriving Central American nation he had invented entirely — flag, currency, guidebook, and all. He sold land and bonds to hundreds of investors, and worse, sold passage to settlers who sailed across an ocean to a country that turned out to be empty jungle. Many died there, on the strength of a brochure.

The verdict: He did not merely sell a lie; he printed it a national bank, and the audacity of the scale was itself the disguise — no one fakes a whole country, so surely it was real.

Andrew Carnegie's Secret Daughter — Cassie Chadwick, 1900s

Chadwick let it be quietly known that she was the illegitimate daughter and heir of the steel magnate Andrew Carnegie, then borrowed enormous sums against an inheritance that did not exist. Bankers, dazzled by proximity to that fortune and too discreet to verify the delicate matter, lined up to lend. The fantasy held until one of them finally, awkwardly, asked Carnegie.

The verdict: An entire banking establishment declined to check the single most checkable fact in the world, because checking it would have insulted the rich man they were all hoping to be near.

The Sixty-Five Billion Dollar Lie — Bernie Madoff, 2008

Madoff ran the largest Ponzi scheme in history, reporting impossibly smooth returns year after year while sophisticated investors, charities, and banks poured in billions. Professionals who could have understood the numbers chose not to look closely, because the returns were too good and the man too respectable. It unwound only when the broader crash forced the withdrawals he could not cover.

The verdict: The genius of the larger con is never the lie. It is the careful selection of victims who will be too proud, too greedy, or too embarrassed to ask the obvious question.

The Blood That Wasn’t There — Elizabeth Holmes / Theranos, 2015

Holmes raised hundreds of millions on the promise of a machine that ran hundreds of medical tests on a single drop of blood, courting a board of statesmen and a press eager for a visionary. The machine did not work, and increasingly did not work in secret, while the believers — dazzled by the story — declined to demand the demonstration. A jury later named it fraud.

The verdict: The investors bought the founder, the turtleneck, and the narrative, and forgot to buy the one thing on offer: a device that did the thing it claimed to do.

The Heiress Who Wasn’t — Anna Sorokin (“Delvey”), 2017

Sorokin posed as a German heiress worth millions, and on the strength of confident manner and unpaid hotel bills, talked banks, socialites, and luxury establishments into extending her fortunes in credit and hospitality. New York's smart set competed to host her, because being seen near the very rich is a hunger no one likes to admit. A court eventually clarified the accounting.

The verdict: She had no money at all. Her entire capital was other people's terror of being the one who failed to recognize someone important.

Look back across the gallery and notice that the swindlers, for all their nerve, were only half the machine. The other half was the mark — and the mark was rarely a simpleton. He was a banker, an investor, a socialite, a man certain of his own shrewdness, and that certainty was the lever every one of these con artists pulled. The con works because the victim is not trying to be fooled; he is trying to be clever, to be early, to be near the money, to be the exception. Vanity buys what suspicion never would, and there has never been a shortage of buyers.