Sympathy for the Con Man

Confidence tricks have enjoyed a special place in American culture since the 1840s. But three TV shows suggest the image of the likable crook may be evolving.

Peter Krause as the international con artist Benjamin Jones in ABC's The Catch (ABC)

In New York City in 1849, a man named William Thompson stole a gold watch just by asking for it. Strolling down a busy Broadway, Thompson approached a stranger with a strange question: “Have you confidence in me to trust me with your watch until tomorrow?” Eager to prove his good faith, the stranger handed his watch over. Tomorrow came; Thompson did not. As far as street crimes go, it was a funny and largely forgettable one. Thompson himself has been largely forgotten, but he nonetheless retains the unique distinction of being the first so-called confidence man—named for “using the word confidence in his swindle,” as the scholar Johannes Dietrich Bergmann wrote in his landmark 1969 article on the origins of the phrase.

There’s a little of Thompson in every con man, whether real or fiction. Swindlers, grifters, and tricksters are everywhere in American literature and folklore, from Davy Crockett to the likes of Jay Gatsby and Augie March. Thompson himself was a probable inspiration for the inscrutable scammer in Herman Melville’s novel The Confidence Man. Now, another cast of cons appears in The Catch, Sneaky Pete, and The Imposters, all new or newish dramas on TV this year. These characters are all ultra savvy and ultra contemporary; in two cases, they’re ultra rich. But they speak to the same hopes and fears that turned Thompson into a newspaper fascination in the middle of the 19th century. The con artist was born in the same years as America’s expanding middle class, and just as the myth of self-made man was taking flight. And the contradictions of the swindler—on TV and elsewhere—are the contradictions of the myth of American self-making itself.

Sneaky Pete, which premiered on Amazon in the fall and was recently renewed for a second season, stars Giovanni Ribisi as Marius, a card shark and high-stakes grifter reduced to a more desperate swindle after a stint in prison. He’s not long out of jail before his previous mark, a gambling impresario played by Bryan Cranston, kidnaps his brother for a hefty ransom. So Marius poses as his cellmate, Pete, and pays a visit to Pete’s loving and long-estranged grandparents with the hopes of an easy score. But Pete’s family, of course, happens to run a bail-bond business, and Pete’s grandmother, played with a watchful warmth by Margo Martindale, has some extralegal schemes of her own. Marius, who started out trying to take their money, ends up trying to save Pete’s family from themselves and quickly becomes an unusual thing on television: a crook with compunction.

Both ABC’s The Catch and Bravo’s Imposters feature similar characters. The Catch, which recently returned for its second-season premiere, stars Mireille Enos as Alice, a private detective in Los Angeles who discovers that her cosmopolitan fiancé, Christopher, played by Peter Krause, is an international grifter who’s emptied her—and her business’s—savings account. As Alice hunts him down, a regretful Christopher (a.k.a. Benjamin Jones) tries to undo the damage, and con his way out of his own con. Imposters has a similar premise, with Inbar Lavi playing a crook named Maddie who courts a series of both men and women to separate them from their savings. She’s a flintier, funnier antihero than Christopher/Benjamin or Pete, but ultimately just as divided. It’s not long before she, too, has feelings for a would-be mark, and the grift gets less glamorous.

These cons all share a heavy conscience, but the shows themselves are refreshingly lightweight. They’re swift and soapy, and take obvious pleasure in the procedural flair of the schemes themselves—the deftly picked pocket, the improvised lie. Tonally, these series call to mind new and old caper classics like American Hustle, Dirty Rotten Scoundrels, Catch Me If You Can, and, most notably, The Sting, referenced specifically in Sneaky Pete. But what made those earlier films so enjoyable to watch was the fun that everyone seemed to be having in them. Think of Amy Adam’s delightfully put-on posh accent in the opening scenes of American Hustle, or The Sting, scored, tellingly, with the familiar piano refrain of “The Entertainer.” Catch Me If You Can saw confidence tricks as a kind of felonious job fair, with Leonardo Dicraprio’s character trying on a number of teen-dream careers for size: pilot, lawyer, doctor. Those movies occasionally explored the moral fallout of scamming, but they also documented the joys of self-invention—of revising your past and devising your future.

The cons of caper films, in other words, so often come across as buoyant enterprisers, cut from the same cloth as the American ideal of the self-made man. That ideal, like the confidence artist himself, came of age in the middle of the 19th century. Thompson carried out his famous watch-pocketing in 1849, as the industrializing cities swelled with young transplants from rural populations. Advice manuals with titles like Young Man’s Guide and Young Man’s Friend all cautioned carpetbaggers against the moral perils of city-living—gambling, drinking, assorted forms of dissipation.

But what brought men to the city, as the scholar Karen Halttunen writes in Confidence Men and Painted Women, wasn’t the promise of city vices. It was the broad promise of the “middle class,” denoting not a mid-way point between the rich and the poor but, precisely, the freedom to be either. Every American, or so the thinking went, could fashion himself into a person of his choosing, whether a drunken gambler or a quintessential man-on-the-make. This new ethic of success propelled the nascent industrial economies, leading some to believe, like the missionary Calvin Colton, that America had become a “country of self-made men.”

That optimism drew on many aspects of the American heritage: Calvinist morality; Benjamin Franklin’s maxims for self-improvement; Thomas Jefferson’s theories of a natural elite; Ralph Waldo Emerson’s case for self-reliance. It also lent the con artist a mythic, keenly American quality. Not long after Thompson’s theft, a letter writer to Boston’s Evening Transcript declared swindlers “indigenous characters […] in our courts and cities.” Ten years later, a pamphlet titled Tricks and Traps would claim con men as “a class peculiar to the West, found operating more or less extensively in every city.” By the 1850s, the very word “Yankee” was a near-synonym for confidence tricks: It connoted the figure of the Yankee peddler, an itinerant scammer hustling his way across the country.

Perhaps no one is more equipped to embody the American ideal of self-determination than the con—the figure who, through sheer imagination, becomes any person of his choosing. At his most benign, he incarnates the “discriminating irreverence” that Mark Twain described as “the creator and protector of human liberty,” and which buoys many of his own grifter characters. But the same qualities that make for a uniquely American hero also make for a uniquely American menace. In the wake of the Thompson craze, an anonymous satirist in the New York Herald compared Thompson’s shenanigans with those of New York’s burgeoning financial elite:

Those palazzos, with all their costly furniture, and all their splendid equipages, have been the product of the same genius [as Thompson]. His has been employed on a small scale in Broadway. Theirs has been employed in Wall Street. That’s all the difference. He has obtained half a dozen watches. They have pocketed millions of dollars. He is a swindler. They are exemplars of honesty. He is a rogue. They are financiers.

This writer wasn’t merely disparaging New York’s rich as common crooks. The point—a radical one for the time—was that crooks would always be common in corporate America. That is, if confidence tricks were the stuff of petty criminals, then they were also essential strategies in a market economy increasingly based on capitalist speculation.

This claim may have been barnstorming provocation in the 19th century, but today, that observation seems starkly prescient. A con man can be many things, but he has always been a fact of free enterprise: His genius is in exploiting the boldness that capitalist venture demands. While first espoused in the writing of Benjamin Franklin, confidence tricks have remained essential in advice literature for the corporate world, most notably in Dale Carnegie’s bestselling self-help book for business people, How To Win Friends and Influence People. Franklin may be America’s best known self-made man, but so, after a fashion, is the imprisoned fraudster Bernie Madoff, whose misdeeds have already been enshrined in a TV miniseries—and both men have been described as cons. That’s because the con is as ambivalent as the success ethic itself, which extends its promise to Emersonian self-cultivators and duplicitous schemers alike.

As that promise has waned, the word “con” has attached itself more firmly to the financial class. It has become common, in recent decades, for Wall Street’s critics to equate corporate mendacity with confidence tricks. In his 2011 book Confidence Men, the journalist Ron Suskind characterizes the events that led up to 2008’s global financial crisis as a “confidence game constructed between New York and Washington.” So, too, does Christine S. Richard compare Wall Street tactics to confidence games in her book on the “activist investor” Bill Acker, 2012’s aptly titled Confidence Game. The Wall Street swindler has become a cinematic archetype of his own, from Michael Douglas’s iconic turn as the id of ’80s wealth culture in Oliver Stone’s Wall Street to Adam McKay’s explanatory comedy-drama on the housing bubble, The Big Short. In public life, the word “con” now appears more often in association with Wall Street scions than small-time hustlers.

Perhaps that fact can’t help but modify, on some level, how Americans appreciate the con in caper stories. It’s difficult, now, to watch an adolescent Leonardo DiCaprio burn happily through millions of dollars of other people’s money in Catch Me If You Can without thinking of his later character, Jordan Belfort, doing the same thing less adorably in The Wolf of Wall Street. At a time when the reach of such misbehavior can plausibly extend into public coffers and public offices, spectacles of stolen wealth might not be as sympathetic as they used to be.

Which could be one reason the new cons on TV are at such pains to be likable. Marius on Sneaky Pete longs to belong to an average American family, even as he threatens to send an average American family into bankruptcy. Christopher/Benjamin in The Catch and Maddie in Imposters want relationships built on trust rather than on skilled deception. These shows balance the romance of the con with the receipts of its cost: broken hearts and empty bank accounts. And what drives these charlatans isn’t confidence, in fact, but a moral sensibility, and a belated desire for atonement.

The idea of a contrite con is, of course, a soothing fantasy—and a curiously apolitical one. These new swindler shows unfold in a nostalgic world where cons are still crafty self-starters rather than corporate villains, and where the stakes of a deception are still relatively small. They offer no explicit comment on any real-life crises and have little interest in tracing the morphologies of wealth and power. But there’s a grim statement nonetheless in their chronicles of fraudsters redeemed. If the only thing that can stop a confidence man, after all, is conscience, what’s to stop the confidence man without one?