The confidence man does not steal, as linguist David Maurer explains in The Big Con, his study of the underworld: “The trusting victim literally thrusts a fat bankroll into his hands.” Victims of grifters, hucksters, con artists and cheats want a return that’s too good to be true. And as long as greed exists, the sharks—from street hustlers to Wall Street financiers—will find plenty of suckers more than willing to be their prey.
In The Big Con, his compendium of crime, David Maurer writes, “Of all the grifters, the confidence man is the aristocrat.” Con men, he explains, unlike mobsters and hooligans, abstain from violence as they convince their victims to hand over their money. However, the gritty film The Grifters, based on Jim Thompson’s 1963 novel, casts some of Maurer’s contentions in doubt, as the movie’s deviants beat, rob and kill one another; one is described, with admiration, as “so crooked he could eat soup with a corkscrew.” Roy and Lilly Dillon (John Cusack and Anjelica Huston), perhaps the most disturbing mother-son team since Jocasta and Oedipus, perpetrate mostly “short cons.” He rips off bartenders and fools chumps with dice; she cheats at the racetrack. Riskier “long cons”—elaborate tricks with multiple players designed to dupe someone out of not just a wallet but a bank account—are the province of Roy’s scheming girlfriend, Myra Langtry (Annette Bening). Maurer considered the long con the pinnacle of criminal artistry, but the hardscrabble cheats of The Grifters don’t derive much satisfaction from their endeavors. Each swindle ends with a desperate search for the next or for a way out of the low life.
Instead of analyzing the prose of the Western canon, linguist and English professor David Maurer probed the seedy shenanigans and pithy patter of grifters. He entered the underworld of “plingers” (street beggars), “whiz mobs” (pickpocket teams), “marks” (victims) and “ropers” (those who lead marks into a scam) and in 1940 published his research in The Big Con: The Story of the Confidence Man and the Confidence Game. Maurer’s book details various machinations that lawbreakers of the 1920s and ’30s employed, both short cons (with immediate payoffs) and big or long cons. One elaborate example, requiring a hefty cast of hustlers and a fake store or club where the scheme unfolded, reeled in a rich mark with three different deceptions—the “wire,” “payoff” and “rag.” Businessmen in real estate, the “fattest and juiciest of suckers,” were choice targets.
Thousands of well-off people were roped in by the biggest con to date, financier Bernard Madoff’s fraudulent investment business, which for at least two decades used investors’ money to prop up an unsustainable Ponzi scheme, paying earlier contributors “earnings” with money taken in from new investors. By 2008 his crooked pyramid was so unbalanced it collapsed, wiping out approximately $17.5 billion in investments.
In his research into the world of con men and grifters, David Maurer distinguished “coppers” (uniformed police officers), “fuzz” (plainclothesmen), “whiskers” (federal agents), “whiz dicks” (lawmen who target pickpockets) and other law enforcement officers—some playing on both sides of the law. A cop who could be paid off was a “tin mitten” (he liked to hear the clink of coins in his hand). If the fuzz weren’t corrupt, they were often targets of cocky swindlers eager to make a “sucker out of the law” and enjoy the turnabout of picking a whiz dick’s pocket.
Bernie Madoff suckered the law repeatedly while running his criminal investment scheme. Financial fraud investigator Harry Markopolos spent only five minutes reviewing Madoff’s profits in 2000 before recognizing they were impossible. The Securities and Exchange Commission, the whiskers of the white-collar world, ignored his warning, along with others, including SEC attorney Genevievette Walker-Lightfoot’s 2004 recommendation that Madoff be investigated. Her notes were boxed away, and she was encouraged to leave the agency; later her SEC boss, Eric Swanson, married Madoff’s niece and staff legal counsel. After he was finally busted, Madoff professed to having been “astonished” that he hadn’t been caught earlier.
Traditional scam artists stalk their marks and win their victims’ confidence in face-to-face meetings. Nowadays grifters can cast a wider net, operating within the smoke and mirrors of the internet, working the “dot-con.” Swindlers send thousands of spam emails in hopes of catching a few suckers, or they lurk in chat rooms trolling for easy marks—and the fuzz, whiskers and whiz dicks have followed them. In 2002 the FBI created a Cyber Division that includes undercover internet agents with phony user names to trap scammers and molesters.
Yet vestiges of the old-school con remain. The “Spanish prisoner” trick dates to the French Revolution, when an unknown grifter sent out a letter claiming an escaping marquis had lost his wealth; his servant, sent to retrieve it, had been arrested and needed bail money—the return, of course, would be a large cut. In one dot-con version of 2013, an email was circulated from a purported American soldier in Iraq who had accumulated millions of dollars in cash sent there as part of the U.S. occupation. To move it safely out of the country, all he needed was an American bank account number. Sound too good to be true? It was.
Robert Redford and Paul Newman, stars of Butch Cassidy and the Sundance Kid (1969), reunited four years later in The Sting, a ragtime-themed ode to the pin-striped grifters of the 1930s. Redford and Newman play confidence men—Johnny Hooker and Henry Gondorff—out to avenge the murder of a friend by mobster Doyle Lonnegan (Robert Shaw). They do so with a long con known as the wire, setting up a fake gambling parlor and reeling Lonnegan in with the promise of an inside man at the horse track who will allow a late bet.
In The Sting’s romanticized criminal world, Redford and Newman’s thieves are witty, stylish heroes, and there is never any doubt that every card in their trick will fall into place. The makers of the movie, apparently, were not so slick: A year after its release David Maurer filed a $10 million lawsuit claiming the story was stolen from his book The Big Con. The suit was settled out of court in 1976. A professor at the University of Louisville whose other books include one about Kentucky moonshiners (“probably America’s oldest continuously operating professional criminal”), Maurer died of a self-inflicted gunshot wound in 1981.
Somewhere in Colombia, it is rumored, budding grifters attend the School of Seven Bells, a sort of Hogwarts for pickpockets. To graduate, the delinquents must steal from their teacher’s person seven objects rigged with bells, without making a sound. In The Grifters, aspiring hustler Roy Dillon solicits tutelage from a master of sleight of hand, who asks Roy for $20, pretending he’s going to teach him a trick with it. “Come around tomorrow,” the swindler taunts the boy before walking off with the money, “I’ll take you again.” Lilly Dillon’s schooling is rougher, coming from a bookmaker who presses the lit end of his cigar into her hand when she cheats him.
Apollo Robbins, a performer dubbed the Gentleman Thief, is considered the world’s greatest pickpocket. Robbins had no apprenticeship but studied martial arts, psychology and ballroom dancing—and scrutinized David Maurer’s Whiz Mob: A Correlation of the Technical Argot of Pickpockets With Their Behavior Pattern (1964)—to piece together his methods. His “college and graduate school education” was a four-year stint at a Las Vegas club, where he was hired to entertain guests waiting to be seated. He did so by picking their pockets, an estimated 81,000 of them.
In the early years of the 20th century, George C. Parker sold the Brooklyn Bridge, the Metropolitan Museum of Art, Grant’s Tomb and the Statue of Liberty—all more than once. This enterprising con man proved that if a cunning crook can exploit the insecurities and desires of a victim, the sky is the limit. Theatrical pickpocket Apollo Robbins explains that he uses psychology and thinks “through the other person’s mind.” He manages to manipulate the attention of his victims (including fellow illusionist Penn Jillette) even when they are well aware of his intentions. Robbins collaborated with neuroscientists Susana Martinez-Conde and Stephen Macknik on their 2010 book Sleights of Mind: What the Neuroscience of Magic Reveals About Our Everyday Deceptions, which examines the ways a professional illusionist can deceive the brain. Thanks to his unsurpassed talent for reading people, Robbins has been tapped to lecture law enforcement groups, collaborate with ex-C.I.A. members and work with the Department of Defense to help develop new military training not just in the art of deception but also in observing human behavior. As David Maurer explained, the psychology of the pickpocket is far less important than the psychology of his victim.
Hucksters, hustlers, grifters and thieves of all kinds turn up in the novels of Charles Dickens. There was not a scam, ploy or flimflam that Dickens did not celebrate. He wrote about child pickpockets swarming the streets of London in Oliver Twist (1838). He filled Martin Chuzzlewit (1844) with greedy swindlers, from the architect Seth Pecksniff, who robs his students of their money, to Jonas Chuzzlewit and Montague Tigg, who form a fraudulent insurance company. Among the most damaging of Dickens’s crooks is Mr. Merdle of Little Dorrit (1857), a banker who uses a Ponzi scheme to amass his wealth. When the fraud crumbles, destroying his family and other victims, Merdle commits suicide. But he won’t be the last of his kind, one character asserts: “The next man who has as large a capacity and as genuine a taste for swindling will succeed as well.” Merdle and his real-life successor Bernie Madoff offer a cautionary tale. Madoff allegedly attempted suicide with his wife after it was revealed that his bogus fund had depleted the savings of thousands. Their son Mark committed suicide two years later. Madoff, at age 75, received a 150-year prison sentence for his crimes.