THE FIRST TIME I was conned, I lost all the money I had in the world.

I was something like 15, right in the middle of a postadolescent rebellion that was typical of white suburban Jews, and I’d been spending increasing time with a rotating cast of seedy types in neighboring Cambridge: would-be punks, grungy homeless teens, the classic “dropouts and burnouts” from the cautionary tales spun in substance abuse prevention programs. Some summer evening when we were smoking pot and drinking malt liquor or shoplifting, some grungy punk I knew (did I know him?) needed help cashing a check. I was happy to help, depositing the thing into my account and handing off the $200 I’d saved running errands and doing chores for neighbors. I didn’t realize what I’d done until the bank called.

We’ve all been there. We’ve lost money on games of chance like a sidewalk dice game or a $1.5 billion Powerball jackpot, even organized trips to Atlantic City and Vegas to willfully surrender our good judgment. We’ve been hoodwinked by psychics and astrologers, street hustlers and panhandlers, guilted into buying fossils or sunglasses that are immediately not worth the money. We know people who’ve fallen victim to cons, from $20 on a rigged dice game or $18,000 to the nice-sounding man who said he was from the IRS and that I needed to pay, now, quickly. Even as the internet’s demolished barriers to human connection, online fraud costs the world more than $100 billion a year. There is probably no experience more universal than getting fucked over.

But the confidence game isn’t just a street-level crime, a peculiar brand of deception and theft that’s the provenance of thieves and scoundrels, but part of all systems where the end goal is to win. Consider that the most hated people of 2015 are all, at a fundamental level, con artists. Martin Shkreli, the loathed “pharma bro” whose face became the most punchable symbol of corporate greed since Gordon Gekko, wasn’t arrested for his notorious price gouging of life-saving AIDS drugs but for defrauding investors in a Ponzi scheme that evokes shades of Bernie Madoff. Bill Cosby’s crafted aura of paternalism and familiarity has collapsed amid a deluge of rape allegations, revealing the real man within. Rachel Dolezal, the Washington State NAACP leader “outed” as a white woman despite her claims of African-American identity, was accused of deliberately and meticulously passing for personal gain. Religious zealot and reality star Josh Duggar hid a life of sexual impropriety and infidelity despite preaching a life of abstinence and virtue. And Donald Trump hasn’t just managed to pass himself off as conservative, but as something more than a TV charlatan to an entire swath of the American electorate. It may seem like we are living in the era of the con.

But are we? The “confidence game,” despite earning its name as recently as 1849 in the New York Herald, has been a part of the human condition since the start of civilization. It’s “the oldest story ever told,” writes New Yorker contributor Maria Konnikova in her new book The Confidence Game: Why We Fall for It … Every Time. “The story of belief — of the basic, irresistible, universal human need to believe in something that gives life meaning, something that reaffirms our view of ourselves, the world, and our place in it.” For Konnikova, fraudsters and iconoclasts like Shkreli and Trump aren’t simply liars and psychopaths, their victims rubes and morons. Both grifter and mark are navigating the most fundamental part of living with other people: trust, and when we share it.

Then again, it’s hard to quantify the economics and cultural footprint of a lying society, let alone infer a rising tide of deceit and scamming despite the horror stories that grace cable news and social media. It’s this challenge that makes The Confidence Game such an engaging read: between studies and statistics, Konnikova threads her examination with rich narratives of historical swindles, from the infamous “Great Imposter” Ferdinand Demara who posed as surgeon Joseph Cyr and saved the lives of several Korean soldiers on the HMCS Cayuga during the Korean War, to the fairly unknown Sylvia Mitchell, the New York psychic who scammed more than $128,000 out of a Singaporean businesswoman, among other victims. The rogues gallery of schemers and liars conjured by Konnikova’s painstaking research isn’t just made up of colorful anecdotes, but is a subtle yet powerful reminder that the con man isn’t solely a shadowy grifter but as ubiquitous and common as the little white lies we tell our friends and family. The best con artists aren’t the now-infamous villains like Dolezal or the boisterous Trump: after all, part of a successful con is to go unnoticed.

This is the real project of The Confidence Game: to build a psychology and typology of the con artists, and their victims, who find themselves in the delicate dance of the swindle. Konnikova, despite her seemingly endless parade of rogues, is more interested in divining something like a game-theoretical model of the con artist as rational actor, based on her idea that a portion of society will rip each other off given “opportunity and a plausible rationale,” as Konnikova puts it. This makes sense, of course: in a society where cooperation and generosity are generally considered a dominant social strategy, the moral ambivalence and “calculated nonchalance” of con artists can be an effective evolutionary adaptive strategy so long as it’s the minority one. “We feel warm and fuzzy when we’ve help someone,” muses Konnikova. “We feel shame or guilt when we’ve lied or cheated or otherwise harmed someone [… but] a very small number of people may have evolved to take advantage of the general good of others.”

The portrait of the con artist Konnikova paints is vivid and alarming. While criminal psychologist Robert Hare theorized that some one percent of the male population is made up of psychopaths — people who fundamentally lack human empathy — the pathology on display in the art of the con is far more complicated and subtle, and likely captures a far broader swath of society. Konnikova argues that psychopathy is just one of the psychological “dark triad” of antisocial traits: psychopathy, narcissism, and Machiavellianism. Konnikova’s troupe of grifters, from Demara to Mitchell, suggest that con artists aren’t just emotionally dead in the way we imagine psychopaths on Wall Street, but manipulative, aggressive, exploitative, and fundamentally self-involved, emboldened by their schemes and machinations even when discovered. The con is something of an emotional master, able to wheedle his way through the cracks in human nature and invade our sense of reality. Konnikova points to “Great Imposter” Demara, who, when outed by journalist Robert Crichton as a prolific grifter, wormed his way back into Crichton’s life, soliciting him for money and even babysitting his children. “Now that,” writes Konnikova, “is a true artist.”

Unfortunately, you can’t see a dark triad just by looking at someone’s face; often, we just see ourselves. We’re notoriously bad at picking up on lies, mainly because we all lie to each other every day, in context, from little white lies on down. Often, the opportunities are set before the grifter even meets her mark; a culture of aggressiveness and amoral behavior (like, say, a Wall Street investment firm) can help push otherwise straightlaced folk toward pulling one over on his clients (or co-workers). It makes sense, as Konnikova points out, that those with the predisposition of a con artist aren’t just petty criminals, but actually overrepresented in legitimate high profile fields of power like politics and law, attracted to less seedy avenues of exploitation and manipulation. After all, what’s better than a con that’s perfectly legal? Grifters are made “when predisposition and opportunity meet,” writes Konnikova: we all have the capacity to cheat and steal, but it takes a certain type of artist to pull off the high-wire deceit of a con when the perfect moment arises. Had Demara been born a few generations later, perhaps he’d be more Bruno Iksil than Joseph Cyr.

If the cunning, opportunistic, aggressive grifter is what the apex of deceit look likes, then what kind of mark falls for it? The victims in The Confidence Game aren’t particularly incompetent or foolish or naive — and that’s what makes them piteous and relatable to those of us who’ve been conned ourselves. All are taken in, as Konnikova writes, by that irresistible desire to believe, to have something be real. And often, Konnikova finds, that’s in a moment of desperation. Consider Lee Choong, the Singaporean businesswoman in a romantic and occupational rut who fed faux psychic Sylvia Mitchell $128,000 for a glimmer of insight into her suffocating funk. Or Robin Lloyd, a recent New York transplant who blew her money in a street game of three-card monte because she was hard up for cash and “completely out of her element.” Or the sailors on the HMCS Cayuga, bloody and dying, in desperate need of anyone, someone, to make things right.

“It’s not who you are, but where you happen to be at this particular moment in your life,” explains Konnikova.

If you’re feeling isolated or lonely, it turns out you’re particularly vulnerable. Likewise if you’re going through a job loss, divorce, serious injury, or other major life changes, are experiencing a downturn in personal finances, or are concerned with being in debt. People in debt, in fact, are also more likely to fall for fraud that’s completely unrelated to finances.

When things are down, it’s that faint glimmer of hope that makes us so susceptible to our local grifter. What was once an evolutionary strength has become a weakness.

There’s a fascinating horror that unfolds while reading through Konnikova’s analysis. In sketching her typology of the con — a predisposition for cunning, a weakened mark marred by personal upheaval, and a golden opportunity in a chance meeting between the two — Konnikova unwittingly illuminates why America seems disproportionately overrun with professional grifters, more than at any time before. And it’s not just that there are more anonymous put-up pros like Demara and Mitchell — after all, the best con is one the mark doesn’t notice and never discovers — or even the now-ubiquitous and generally harmless internet scams, but more brazen frauds perpetrated against the public. Trump, Shkreli, and even Cosby all carry the hallmarks of a con: a cunning, ruthless personality (Cosby the psychopath, Trump the narcissist, and Shkreli the Machiavellian, perhaps?) playing on an innate weakness in human nature, the desire to believe at a desperate time. This could easily be a description of Donald Trump’s campaign.

Actually, though! Even when you look past his cutthroat business practices and financial largesse, Trump displays all the trademark dark triad traits, from psychopathy (see: his campaign) to narcissism (see: Trump tower; his campaign) to Machiavellianism (see: Donald Trump). Trump isn’t the blatant con artist at your corner dice game, but an experienced, masterful executive. His manipulative tendencies are strengthened by his showmanship, his instant name recognition (“The people committing these crimes are doing them from hundreds of miles away,” said legendary Frank Abagnale of internet scams. Trump’s actually built a rabid fan base from behind a keyboard), his arrogant confidence, and his minor but enduring mythos in American pop culture. Trump has trolled the American public into thinking he’s running for president since 1988 before refining his image on The Apprentice, and we’ve eaten it up.

But America in 2015 was the classic mark: desperate, anxious, in an anomic free fall. The economy is recovering, but manufacturing jobs have disappeared and aren’t coming back. Wages remain stagnant. And the anger felt by white men that their jobs are gone and the world is increasingly out of their control — perhaps best captured in the backlash to LGBT legal victories and the national conversation on race and police — makes for a desperation perfect for manipulation by a master showman. Trust in the American establishment, from Congress to the White House to other major institutions of civil society, is at an all time low: If you ask the average American, they’ll tell you that every major institution in American civil society, from Wall Street to K Street, is ruled by vultures and opportunists looking to exploit the weak and powerless. But Trump captures the national imagination despite having never held an elected office, a sick twisted caricature of William Jennings Bryan or Huey Long, but tapping into that anxiety and riding it to the top.

“We’re dying. We need money … We have losers,” said Trump when he entered the Republican race in June. “We have people that don’t have it. We have people that are morally corrupt. We have people that are selling this country down the drain … The American dream is dead.” The master salesman found a story to sell to a buyer desperately in need of one — the grifter found his mark. But then again, the American dream is alive and well in Donald Trump; as Konnikova says, with the right predisposition and the right opportunity, even you could con your way right to the top.


Jared Keller is a writer living in Brooklyn, New York. His work has appeared in The AtlanticBloomberg BusinessweekOutsidePacific Standard,
Smithsonian, and many other outlets.