Our topic today is useful and instructive: how to be (and how not to be) a successful con artist. I am drawing inspiration from an article in the New York Times’s business section, which compares and contrasts the treatment of the two examples, Elizabeth Holmes and Martin Shkreli. Both, it turns out, are scammers, but their legal treatment has been very different.

 

The reporter, James Stewart, notes that Holmes’s crimes were more successful for a longer time than Shkreli’s, and did far more damage to more people. Yet her punishment, after a long and dazzling run of success, amounted to little more than a slap on the wrist. He got a seven-year prison sentence.

 

You probably remember both of them. Holmes dropped out of Stanford at 19 to found a company, Theranos, to manufacture and sell a method she had purportedly developed to enable blood tests to be done using only one drop of blood. The method never was seriously tested and, despite Holmes’s repeated statements to the contrary, never worked. Yet Theranos received support – membership on its Board of Directors, large investments, glowing encomia – from a great many powerful, knowledgeable, and wealthy people, many of whom really should have known better. The totality of the fraud is estimated at around $700 million.

 

Shkreli’s crimes included “an egregious multitude of lies” (according to the sentencing judge) in support of securities frauds amounting to a mere (or “mere”) $10 million. Shkreli claims to have repaid a majority of his investors, some of whom made millions. Holmes’s investors have lost their money.

 

Stewart explains the discrepancy in their treatment on a number of grounds: she is a sympathetic person, low-key and demure; he is brash and obnoxious. What exactly does that distinction mean? What makes her “nice” and him “nasty”? And is it the case that our criminal justice system discriminates on the basis of perceived personality?

 

Shkreli’s criminal defense started out two strikes behind in the game of public sympathy. He ran a pharmaceutical company, Turing Pharmaceuticals, that bought up generic drugs for rare diseases very cheaply and raised their prices astronomically – in one case, from $13.50 to $750 a dose. But there’s nothing illegal about this, and it did not figure directly in his trial or sentencing: it’s merely an example of triumphal capitalism, not too different from the behavior of certain persons currently in very high places.

 

But many prospective jurors in Shkreli’s trial – before they had heard any testimony – asked to be excused because they had heard about his other behavior, the price-raising and his obnoxiousness when testifying about it to Congress (for instance, tweeting later that the Congressmen were “imbeciles”) and felt they could not give Shkreli a fair hearing. So very probably his legal, if loathsome, drug-pricing influenced his verdict and sentencing, unfair as that may be.

 

Arguably, Shkreli suffered the same kind of vengeance as O.J. Simpson. In 2007 Simpson, with several buddies, broke into the Las Vegas hotel suite of a sports memorabilia dealer to steal some items that had belonged to O.J. and which he claimed had been stolen from him. They had guns, but no shots were fired and no one was hurt. Simpson was found guilty on 12 counts and sentenced to 33 years in prison, with parole eligibility after nine. He was paroled in 2017.

 

This seems an astonishingly harsh sentence for an unsuccessful and harmless attempt at a minor crime. The only way to understand it is to see it as payback for the acquittal most of us felt Simpson did not deserve. Analogously, Shkreli’s harsh verdict was not about the securities fraud with which he was charged, but for his perfectly legal but reprehensible drug-pricing.

 

But that delayed revenge doesn’t fully answer the question: what personal behaviors or self-presentations worked so well for Holmes and so badly for Shkreli? The choices each made comprise a narrative about how to be, and how not to be, a successful crook. For the aspiring con artist, knowing how to communicate – linguistically and otherwise – has a lot to do with how successful one is.

 

Holmes and Shkreli start out with some of the same pluses: they are young, attractive, highly articulate, and well educated. But the similarities stop there.

 

The two have different notions about the manipulation of physical appearance. Shkreli shows up in court and in Congress, formal places, with his hair unkempt and unstyled. Where most men would wear a formal suit and tie, he wears his shirt open at the neck. Both the judging bodies and TV viewers see Shkreli’s choices as thumbing his nose at the institutions we want to respect.

 

By contrast, Holmes has carefully manipulated everything about her physical appearance to enhance her scientific stature and our personal sympathy. You might think that might raise suspicions – is she trying a little too hard? — but we admire her for looking the way she ought to look. She cares about every detail, we think approvingly. She cares what we think about her. Her careful coif, makeup, and dress said to us, especially to older people: I’m one of you. I share your values. You can trust me, despite my youth. Her honey blond hair is not platinum, which would convey frivolousness, but just blond enough to be alluring. She wears just enough makeup – a little lipstick, eye liner, foundation, and a touch of blush – to convey: I care what you think about me, but I don’t want you to like me for my sexiness. She needs you to like her, but not to be overwhelmed by her.

 

In the photos in the article, she is making eye contact with the camera – she’s open, she’s friendly. His eyes are downcast in one, looking mischievous in the other – neither trustworthy. Her expression is an engaging half-smile, his a smirk.

 

Then, too, there is her invariable costume: a black pantsuit with black turtleneck shirt. It plays to us as a uniform. It is serious and not casual, carefully thought out. Uniforms like hers partially deny the wearer’s individuality, the antithesis of flirtation. This is a serious person, one who puts her research above her self.

 

The uniform also mirrors the uniforms of some highly successful men in Silicon Valley: Steve Jobs’s black long-sleeved tee shirt and blue jeans; Mark Zuckerberg’s former hoodie and current worn purplish short-sleeved tee and jeans. Her pantsuit cis more formal but makes a similar point: the wearer is too busy doing good work to have to think about what to wear every day.

 

So in every way in which they control their appearance, demeanor, and deportment, her choices are winning and persuasive and his the opposite.

 

One more thing separates them, even though they have no control over it: their last names.

 

Shkreli: what’s wrong with it? Everything. Clearly foreign. Impossible initial cluster, making it unpronounceable (very inconsiderate!). Ending in –i, as American names don’t. And thus conveying subliminally: I’m not one of you. Don’t trust me.

 

Holmes. Completely English and easy to pronounce, especially if the l is silent. And it has the very best associations. There are the New England Oliver Wendell Holmeses, father (doctor and patriotic poet) and son (illustrious attorney and Supreme Court justice): what could be more quintessentially American, more worthy of reverence? In case you’re an Anglophile, there’s Sherlock: logical, brilliant, on the right side of the law, thoroughly scientific, and always right.

 

What’s in a name? A lot, if it’s the right, or wrong, kind of name.

 

Justice is not blind or deaf. We make decisions about whom to trust without recourse to rationality. Those who would be deceptive, if they have any sense, are aware of our frailties and play to them. If they don’t have any sense, well – they get the seven years they deserve, not necessarily for their legal wrongdoing, but for their stupidity.