The Confidence Game

  That February morning, he wanted to be sure to make an impression, show those poor Catholic kids how a real gentleman behaves. And so, he made his way to the bakery and candy shop off Jackson Street, close to the house that was no longer theirs. The family, he knew, still had an account there. He arranged for the largest heart-shaped box of chocolates to be delivered to the school at three sharp.

  The box never came. Somehow the order had gotten lost in the mix—or perhaps the confectioner had grown suspicious that the Demaras’ account wasn’t what it once was. Whatever the holdup, if there was one thing Fred hated more than being poor, it was the humiliation of being called a liar. He’d promised the biggest gift the school had ever seen, and he had come up empty-handed. He vowed to make it right. He returned to the store in a huff. This time, he ordered not only the large heart but smaller boxes for every child in the grade. To put on his account.

  This time, there was no mix-up. If the boy had the nerve to order up such a storm, clearly the family could pay. You wouldn’t do something like that, and do it so confidently, unless you could back it up. The boxes promptly arrived, wheeled to St. Augustine’s in a large cart overflowing with chocolate. The Demara family, of course, had no way of paying for them.

  From then on, until, at fifteen, he dropped out to join the first of a string of religious orders, Fred Demara was known as the Candy Butcher. And from there, it was a stone’s throw to his first full-on con: stealing an unsuspecting student’s credentials to try to get a commission in the navy.

  Was the life of an impostor always his destiny? Was he born to be a grifter?

  * * *

  Con artists are evil human beings, with malicious intentions and no conscience. Would that it were so. It would make the world a much easier place to be in. We’d ferret out the bad guys and be on our merry way. The reality, however, is far messier.

  In his essay “Diddling,” Edgar Allan Poe describes the features of the swindler: “minuteness, interest, perseverance, ingenuity, audacity, nonchalance, originality, impertinence, and grin.” Modern psychology agrees with him on one particular point: the nonchalance. For the most part, humans have evolved as cooperative animals. We can trust one another, rely on one another, walk around with a wallet full of cash not worrying that every single stranger will rob us, and go to bed with the certainty that we won’t be killed in our sleep. Over time, our emotions have evolved to support that status quo. We feel warm and fuzzy when we’ve helped someone. We feel shame and guilt when we’ve lied or cheated or otherwise harmed someone. Sure, all of us deviate now and then, but for the most part we’ve grown to be quite decent—or, the opposite of nonchalant. For the most part, we care about others and know that they care to some extent about us. Otherwise, much of society would collapse.

  But there’s an exception. A very small number of people may have evolved to take advantage of the general good of others, fueled by the nonchalance that makes many a con artist what he is. These people don’t care; they remain perfectly indifferent to the pain they cause, as long as they end up on top. It makes perfect sense. If the vast majority of the people who surround you are basically decent, you can lie, cheat, and steal all you want and get on famously. But the approach only works if few take advantage of it—if everyone did the same, the system would self-destruct and we would all end up doing worse. Calculated nonchalance is only an adaptive strategy when it’s a minority one. Or, as Adrian Raine, a psychologist at the University of Pennsylvania whose research centers on antisocial behavior, puts it, “Persistent immoral behavior can be thought of as an alternative evolutionary strategy that can be beneficial at low rates in society. By lacking the emotional experiences that serve to deter immoral behavior, and by using deception and manipulation, individuals may be able to successfully cheat their way through life.”

  There’s another word for this calculated—inbred, even—nonchalance. Psychopathy, or the basic absence of empathetic feelings for your fellow human beings. It’s nonchalance brought to a biological extreme. But do con artists actually fit that bill? Is it fair to say that the Demara-like grifters of the world are more likely than not clinical psychopaths—or are they just slightly more devious versions of our more conniving selves? Is it a qualitative difference between our small daily deceptions and the wiles of the confidence man, or is it just a simple matter of degree?

  Robert Hare’s Psychopathy Checklist–Revised, the most common assessment tool for antisocial, psychopathic behavior, looks for things like responsibility, remorse, pathological lying, manipulativeness, cunning, promiscuity and general impulsiveness, superficial charm, grandiosity, and the like. Score high enough, and you are labeled psychopathic, or “suffering soul,” for the many such you leave in your wake. One of the defining marks of the psychopath is the inability to process emotion like other people. To a true psychopath, your suffering means nothing. There’s no empathy. There’s no remorse. There’s no guilt. When psychopaths experience something that would shock most people—disturbing images, for instance—their pulse stays steady, their sweat glands normal, their heart rates low. In one study of clinical psychopathy, psychopaths failed to engage the same emotional areas as non-psychopaths when making difficult moral decisions—for instance, whether or not to smother a crying baby if doing so would save the entire village while a failure to do so would condemn everyone, baby included. For the overwhelming majority of people, it’s a draining choice. The emotional areas of the brain fight it out with the more utilitarian ones for an answer. In psychopaths, the battle is absent: they exhibit nonchalance in its most extreme form.

  Psychopaths, according to Hare, make up an estimated 1 percent of the male population; among women, they are almost nonexistent (though still present). That means that out of every hundred men you meet, one will be clinically diagnosable as a psychopath. But will he also be a born con man?

  On one level, the data seem to suggest a direct affinity between the two, grifter and psychopath developing hand in hand. One tantalizing piece of evidence: when people acquire the neural deficits associated with psychopathy later in life, they start behaving remarkably, well, psychopathically—and remarkably like a con artist. In lesion studies, people who experienced early life lesions in the polar and ventromedial cortex—areas implicated in psychopathy—begin to show behaviors and personality changes that very closely mimic both psychopathy and the grift. Two such patients, for instance, showed a newfound tendency to lie, manipulate, and break the rules. Others described them as “lacking empathy, guilt, remorse, and fear, and . . . unconcerned with their behavioral transgressions.” Psychopathy, then, is a sort of biological predisposition that leads to many of the behaviors we expect from the confidence artist.

  But that’s not exactly the whole story. Psychopathy is part of the so-called dark triad of traits. And as it turns out, the other two, narcissism and Machiavellianism, also seem to describe many of the traits we associate with the grifter.

  Narcissism entails a sense of grandiosity, entitlement, self-enhancement, an overly inflated sense of worth, and manipulativeness. It sounds, in short, like someone much akin to our Fred Demara, someone who can’t stand to be seen as inferior, who needs to be the center of attention, and who will do what it takes to get there. A narcissist will do everything necessary to preserve his image. It’s Fred lying to the candy store to avoid embarrassment—not the greatest of cons, but one driven by that kind of self-centric tendency.

  But perhaps even more relevant is Machiavellianism—a characteristic that is almost predicated on the ability to deceive, as ruthlessly and effectively as Machiavelli’s most ideal of princes and the most famed of confidence artists, both.

  In the psychology literature, “Machiavellian” has come to mean a specific set of traits that allows one to manipulate others to accomplish one’s own objectives—almost a textbook definition of the con. Writing in 1969, Richard Calhoon, a marketing professor at the University of North Carolina, described the Machiavellian as someone
who “employs aggressive, manipulative, exploiting, and devious moves in order to achieve personal and organizational objectives.” And, indeed, the so-called high Machs—people high on the Machiavellianism scale, a measure first developed in 1970 by two psychologists who wanted to capture leaders’ manipulative tendencies, Richard Christie and Florence Geis—tend to be among the most successful manipulators in society. In one series of studies, when a high Mach was placed in a situation with a low Mach, he tended to emerge ahead in most any scenario. The low Mach would let emotions get in the way. The high Mach, however, wouldn’t be as easily disturbed.

  In one early review, the Machiavellians among eleven distinct samples, including students, academic faculty, parents, children, athletes, the staff of a mental hospital, and business employees, were more likely to attempt to bluff, cheat, bargain, and ingratiate themselves with others. They were also more successful at doing so. In another study, the Machiavellian-minded among us made for more convincing liars than the rest: when people were taped while denying that they had stolen something (half were being honest, and half lying), those scoring higher on the Machiavellianism scale were believed significantly more than anyone else. In a third, business school students had to decide whether or not to pay someone a kickback, a behavior that is largely considered unethical (and is against the law). They were all given a rationale for why, in this case, the kickback made sense. Those who scored higher in Machiavellianism were more likely to take the bait when the rationale made it more cost-effective to do so.

  Machiavellianism, it seems then, may, like psychopathy, predispose people toward con-like behaviors and make them better able to deliver on them. Delroy Paulhus, a psychologist at the University of British Columbia who specializes in the dark triad traits, goes as far as to suggest that “Machiavellian” is a better descriptor of the con artist than “psychopath.” “It seems clear that malevolent stockbrokers such as Bernie Madoff do not qualify as psychopaths,” he writes. “They are corporate Machiavellians who use deliberate, strategic procedures for exploiting others.”

  So wherein lies the truth: is the con artist psychopath, narcissist, Machiavellian? A little bit of all? Demara seems to be proof of the “all of the above” choice. Doctors are often accused of playing God. Demara took that criticism to a grotesque extreme. What ego, what blithe disregard for the lives of others and overconfidence in oneself, can lead someone to not only pose as a surgeon but perform multiple surgeries without any of the requisite qualifications to do so? To place oneself in a position where one is the only medical recourse for hundreds of men? It seems not only the height of narcissism, but, too, the most psychopathic of behaviors: the power to kill who knows how many others. And what a dose of Machiavellianism that must entail, to convince a nation’s army and manipulate other doctors, a captain, soldiers, the whole lot that you’re the real deal.

  Demara wasn’t humbled by his stint in Korea. Quite the contrary. He was emboldened. When Robert Crichton set out to write his biography, the impostor spent days convincing him to let him deliver his pregnant wife’s baby. He could, he assured him, do it better than anyone else. Why rely on a hack when you could get a real medical expert? Crichton, of course, knew, rationally, that Demara had no training to speak of. But he had saved those soldiers. And he had read all those textbooks—probably more closely than your average doctor. The more Demara cajoled, the more Crichton’s resolve to tell him, once and for all, that his wife was off-limits weakened. It took Crichton’s wife, Judy, to put a lid on the plan: he had put the proposal before her in all earnestness.

  Now that’s a true artist.

  Actually, here’s the true artistry: even after this mishap, as we’ll call it, when Judy told Bob that Fred wasn’t to set foot in their house again, her resolve, too, eventually melted away. It was only a few years after the Great Impostor went away—and after he’d sued Crichton and Random House for allegedly withholding funds—that that same Judy let him babysit their toddler daughter.

  Now that’s a true artist.

  * * *

  But the Demaras of this world are only part of the picture. It is possible, it turns out, to possess all the tenets of the dark triad, and then some, and still not turn to con artistry. Psychopaths, narcissists, and Machs may be overrepresented in the grift, but they are also overrepresented in a number of other professions that line the legitimate world. As Maurer puts it, “If confidence men operate outside the law, it must be remembered that they are not much further outside than many of our pillars of society who go under names less sinister.” Leadership and high-profile roles. Wall Street. Politics. Law. Test most any of them, and you’ll find a percentage of psychopaths and dark-triadists that makes Hare’s 1 percent estimate look naïvely low.

  When Shelby Hunt and Lawrence Chonko gave the Machiavellianism scale to one thousand professional marketers, they found that over 10 percent scored in the highest possible range—and far, far above the population average. In other words, they were among the highest possessors of traits that hinged on manipulation and deception. And yet, they engaged in a legitimate business. None of them were criminals. None of them were even aristocrats of crime.

  The dark triad pushes people in the direction of manipulation—Christie and Geis found that the highest Mach scorers among doctors had consistently chosen to be psychiatrists, a field where manipulation and mental control are central, while, in a separate study, Machiavellian students were more likely to specialize in business and law than any other areas—but it does not compel them to push that manipulation beyond a point that’s generally socially accepted.

  And while some would doubtless argue that I’ve just made my own point—what are politicians, lawyers, businessmen, admen, and marketers but thinly veiled con artists?—the truth is that real con artists aren’t simply born. They are, as is usually the case, made as well. As the popular saying among scientists goes: genes load the gun; the environment pulls the trigger. The exact same traits could easily be put to use in more or less devious ways. The choice is not predetermined. And the presence of Machiavellianism or psychopathy or narcissism no more marks someone as a grifter than the presence of charisma or nonchalance.

  James Fallon discovered he was a psychopath by accident. He’d been running two projects simultaneously: a large imaging study of Alzheimer’s patients, where his own family served as “normal” control brains, and a small side project on the brains of psychopaths. As he was going through the Alzheimer’s scans, one brain popped out. It had all the markings of the psychopath. Hmm. Clearly, someone had made a mistake and mixed one of the psychopathic scans in with the Alzheimer’s data.

  Normally, results in typical lab studies are anonymized so that nothing tips the experimenter off to the identity of the subject. In this case, Fallon decided to make an exception. The scan would need to be deanonymized so that they could determine where the data belonged. He asked one of his technicians to run the numbers and find the identity of the scan owner.

  The end of the story is the subject of Fallon’s subsequent book, The Psychopath Inside. There was no mistake. The scan was in fact his own.

  Fallon had been a vocal proponent of the genetics of psychopathy. It, and many other conditions, he’d argued, were largely determined by the luck of the draw. If your brain was psychopathic, you’d simply drawn the short straw. Now that his own brain was at stake, however, he decided to dig deeper. Was it as predetermined as he’d always assumed?

  Today, Fallon believes that the genetics are there, true, but that certain critical periods in your childhood can nudge you more or less toward full-blown clinical psychopathy, so you exhibit some signs, for instance, but not the whole arsenal. Luck out, you become a high-functioning psychopath, like Fallon, and, perhaps, some of the con artists in this book. Get the bad draw, you become a violent psychopath, like the ones who fill up jails and sit on death row.

  Apart from the period in utero, a time that we now know is crucial for the development of your genom
e’s epigenetic markers—that is, the methylation patterns that will determine how, precisely, your genes will be expressed—Fallon believes that the first three years of life play a crucial role in determining your psychopathic future. In that period, a child naturally develops so-called complex adaptive behaviors, like the ability to deal with fear, to smile, to react to those around her. But sometimes that process is interrupted, usually by something particularly stressful. A single traumatic event or a baseline of stress at home or in school could both, in theory, interrupt normal development and make the psychopathic traits you were genetically predisposed to more likely to assert themselves—perhaps in much the same way as they surfaced in Demara after his family’s sudden fall from grace and the total uprooting of his childhood home. But in its absence, a would-be cunning deceiver becomes a respected neuroscientist instead.

  For most people to go from legitimacy to con artistry, three things need to align: not just the motivation—that is, your underlying predisposition, created by elements like psychopathy, narcissism, and Machiavellianism—but alongside it, opportunity and a plausible rationale. In corporate fraud, for instance, few people choose to con in a vacuum. Instead, according to one study, about a third of perpetrators aren’t simply willing to go one step beyond what’s technically legal (predisposition); they also perceive an aggressive sales environment (opportunity) and feel they must do something to stand out (rationale)—a question of company culture and atmosphere meeting a willingness to cut corners and the chance to rationalize away that cutting as a matter of necessity.

  Grifters are made when predisposition and opportunity meet. That’s one of the reasons, according to some sources, that insider trading—when businessmen turn con artist—flourished at Steven Cohen’s now infamous hedge fund, SAC Capital Advisors, for as long and as widely as it did. “You self-justify that it’s not so bad because everybody is trying to get an edge,” a source close to the fund explained over lunch one day. “And it’s less likely that I’m going to get caught because, clearly, somebody would’ve been caught by now.” At SAC, he continued, “There was no evidence that people ever stood up at the top of the firm and said in words that a third grader would understand, ‘By the way, don’t break the law. Don’t cheat, don’t steal—we don’t do that here.’” Take the indictment of the hedge fund itself. “One prospective employee was rumored to have engaged in insider trading at his prior place of employment. And he was hired. Over the objection of the compliance officer. And, shockingly, he started engaging in insider trading within a couple of weeks of joining.”