Con artists are greedy hucksters who sell us possibilities that never come true. But Americans have a soft spot for them. The phrase confidence manwas popularized in an 1849 New York Herald article detailing the arrest of William Thompson, a man of “genteel appearance” who for months had been approaching strangers on the street and somehow persuading them to trust him with their watches until the next day. (Needless to say, they never got the watches back.) Almost immediately, a play titled The Confidence Man debuted; Thompson was soon bragging that he was “a great man in the eyes of the world.” In the decades that followed, the con artist became a classic American antihero.
The curious thing, as the University of Pennsylvania historian Walter McDougall writes, is that “far from despising flimflam artists as parasites or worse, American popular culture habitually celebrates rascals as comedic figures.” Think of the movies of W. C. Fields and the Marx Brothers; think of The Sting and Dirty Rotten Scoundrels. Even bleaker depictions, like David Mamet’s, get us to admire the dexterity with which con artists persuade people to part with their money.
It seems that con artists, for all their vices, represent many of the virtues that Americans aspire to. Con artists are independent and typically self-made. They don’t have to kowtow to a boss—no small thing in a country in which people have always longed to strike out on their own. They succeed or fail based on their wits. They exemplify, in short, the complicated nature of American capitalism, which, as McDougall argues, has depended on people being hustlers in both the positive and the negative sense. The American economy wasn’t built just on good ideas and hard work. It was also built on hope and hype.
In the 19th century especially, the line between crook and businessman was fuzzy. Take the building of the American railroads, which both spurred industrialization and laid the foundation for a truly national economy. When the Central Pacific Railroad (the western spur of the transcontinental railroad) was built, the four men who started it, including Leland Stanford, set up an outside construction company in which they were the sole shareholders, and they used that company to milk the Central Pacific for millions of dollars in excess construction costs. The building of the Union Pacific Railroad led to the same kind of self-dealing and pocket lining and reckless overbuilding, while railroad financiers like Jay Gould made enormous sums via stock schemes and dubious takeovers. The result was one of the biggest cons the country has ever seen, with huge losses for investors and a fortune for the moguls. Still, we ended up with a national transportation system.
In the 20th century, the relationship between commerce and con artistry became subtler. Never mind the out-and-out scammers, from Charles Ponzi to Bernard Madoff, or the long history of questionable behavior on Wall Street. Entrepreneurs have skills that are very much like those of the con men. To raise money to start a business, you’ve got to sell an imagined future—a dream. Before building a single car, Henry Ford had to persuade his major supplier to take stock in lieu of cash because he didn’t have the money to pay for thousands of dollars’ worth of parts.
As the sociologist Alex Preda writes, “Talent for persuasion is key: After all, the public must be convinced to part with their money on the basis of the simple promise that an idea will yield profit in the future.” Successful entrepreneurship involves hucksterism, the ability to convince investors and employees that they should risk their money, their time, and their effort on you. Like a con artist, you’re peddling optimism. As Mel Weinberg (the model for Christian Bale’s character in American Hustle) put it in Robert Greene’s book The Sting Man, “It’s my philosophy to give hope … That’s why most people don’t turn us in to the cops. They keep hopin’ we’re for real.”
In a dynamic economy, getting people to wager on unknowable (and often unlikely) futures is essential. The greatest business icon of our era, Steve Jobs, was legendary for his “reality-distortion field,” which allowed him to convince people that improbable outcomes were not just possible but also certain. Jobs’s endless rehearsals for his public presentations and his scripting of every moment for maximum effect—these are all straight from the con artist’s playbook. So, too, is the sense of conviction he projected. In Weinberg’s words, “Before you sell a deal, you have to live the deal. You have to believe in it because if you don’t believe in it, you can’t sell it.”
Of course, the fundamental difference between entrepreneurs and con artists is that con artists ultimately know that the fantasies they’re selling are lies. Steve Jobs, often enough, could make those fantasies come true. Still, that unquantifiable mélange of risk, hope, and hype provides both the capitalist’s formula for transforming the world and the con artist’s stratagem for turning your money into his money. Maybe there’s a reason we talk about the American Dream.