chasing mr. ripley

on conmen, emotional fraud, collective trust and the eternal question of why liars lie

Back when I lived in Toronto, there was a conman who worked my downtown neighbourhood. Almost everyone I knew had been taken in by him at some point, including me. I remember him vividly. He was handsome and clean cut, a black man in his mid-forties. He wore a dark pressed suit, an overcoat and dress shoes and spoke with an elegant continental French accent. He tended to chat people up at late night, when they were coming back from work or on their way home from the bar. His manner was apologetic, flustered and self-deprecating.

‘I’m very sorry to bother you, but I’m having a bit of an issue,’ he’d say, pointing to a nearby parked Audi or BMW. ‘You see I’ve locked my keys in my car. It was very stupid of me, I feel like an idiot. I’m not sure what to do.’

The big problem, he’d explain if you let him, was the fact that his wallet was back at his house which wasn’t terribly far but he couldn’t let himself in without his house keys, which were also, frustratingly, locked inside the parked car. He couldn’t leave overnight either, because then it would get towed. His cleaner had a spare set of house keys but unfortunately she was away on holiday. The only reasonable solution was to call a 24-hour mobile mechanic out to open the car door — but how? Sometimes he expanded further, claiming he’d been pickpocketed, or that he had a young child he needed to pick up from somewhere, but the key message was simple: He needed $250 cash and he needed it now or he was fucked.

If you tried fob him off with, say, twenty bucks, he’d refuse with a wave and a weary smile, then politely bid you good night turn and walk away. On reflection I think this was why the con worked. His willingness to walk away from the cash, coupled with his meticulous good manners and air of resigned dignity gave extra credence to his story and elicited an emotional response. Looking at his retreating overcoat you’d realise you were on a moral precipice. It was up to you to make a moral decision. Were you going to help this poor guy out or not? I’m sure many people didn’t. But if you called him back (as I did) the deal was clinched. Within a few minutes you found yourself at a nearby ATM, entering your PIN as the conman waited outside at a respectful distance, out of view of the cameras, until finally, you pressed $250 crisp bank notes into his hands.

It was a simple scam but it worked. Dozens of people I knew had given the Frenchman their hardearned cash and then arranged to meet him the following day so he could pay them back (this was before mobile phones were common, which obviously helped a lot). Interestingly, the conman did not vanish immediately after getting his money but instead hung around for a while, flattering you with his gratitude and relief, lavishly praising your decency and kindness. It always ended with a big tearful hug.

Later, of course, you’d realise you were not the valiant hero you’d imagined, but instead a naive fool. The pleasure the conman had presumably taken in highlighting this irony was, in retrospect, both humiliating and darkly funny. A conman’s artistry is not just in fooling people but also in revealing his victims’ weaknesses to themselves later, long after he’s gone.

For years I’ve been thinking about the Toronto scammer’s deeper motivations. The guy was intelligent and charming, after all. There were far less risky ways he could have made $250 a night in Toronto in the late 90s. Here’s a little working theory I’ve developed over time: I think he genuinely enjoyed his work. Not just the cruel perversity of luring good people into a cynical trick (which not terribly difficult) but the intense emotional connection that transpired as a result. In that bonding moment the conman was able not just to make his victim believe he was who he said he was — a decent man in troubling circumstances being rescued by a kindly stranger — he was able to believe it himself. I suspect it was this feeling, the sensation of becoming a better version of himself, he was really after, and which spurred him to work the scam over and over and over again.

It’s just a theory of course. I’m not trying to excuse the Frenchman’s behaviour; I’m just trying to understand it. This is what we do with conmen, for better or worse.

I went down Mr. Ripley rabbit hole this week. First I gobbled up Ripley, latest remake on Netflix, a sumptuous black and white period series starring the delectably furtive Andrew Scott. Then (because my library is now organised) I re-read the original Patricia Highsmith novel, the first in a series. Finally I revisited the 1999 film starring Matt Damon, which made a profound on me at the time, in part I suspect because I was the same age as the twenty-something characters when it came out. After that I delved into the online Ripleysphere and discovered to my delight, I am not alone in my obsession with the shifty mister Tom. There are many of us, which I suppose is why the character and story lives on.

The question of what motivates Tom is a conundrum I often find myself revisiting and connecting to my own experiences of being conned in real life (the Frenchman was only the first time, it must be said). On the surface, the answer is obvious: Ripley is lazy and selfish. He’s a weak character on the fringes of upper middle class society. He lies because it’s the most expedient way of getting what he wants, which is ostensibly an easy life. Tom wants pleasure and self-gratification, but in pursuing it he creates a private hell for himself. The obvious interpretation of the story is that he wants to be Dickie — a confident, good-looking rich kid with a passive income and the adoration of women and men alike. So (spoiler!) he murders Dickie and then impersonates him. Finally, through a series of improbable twists of fate, he somehow manages to get away with it.

What makes the story so ingenious is Tom’s passivity. Most conmen are hustlers, constantly on the make, but Ripley, by contrast, is relatively inert. Most of what happens to him is accidental. His biggest lie are omissions. His crimes are violent and shocking of course, but they are impulsive rather than premeditated. He is, for the most part, a hapless opportunist. He does the wrong thing repeatedly and hamfistedly and yet somehow manages slip through every net.

Ripley’s motivation is the real puzzle at the heart of the story, hence the long stream of adaptations and interpretations. As with all conmen, there is the nagging question of why? What makes an intelligent liar lie and lie repeatedly?

As a journalist I’ve written about several conmen and their elaborate scams over the years. I’ve even had the opportunity to talk to a couple. Most cons I’ve met commit to their stories to the bitter end, the mask never drops. You can pummel them with reason and fact, but eventually you’ll end up exhausted and frustrated. There is no Scoobie Doo moment of reckoning, which is disappointing.

However there was one exception. I once met a conman who, after the gig was up, elected to show me a glimpse of his private torment. He did so, I suppose, because I was genuinely curious and he had no one else to tell. In a series of long conversations, he described his deep sense of emptiness and confusion. I understood that in unburdening himself this way he was trying to elicit my sympathy — that even his honesty was part of the con. But he admitted to lying which is rare. He described to me in detail what it felt like to live in a self-constructed world of lies. His lack of guilt. The complicated lengths he went to in order to hoodwink the people who trusted him. His constant panic at idea of being caught. The thrill he got from living a secret life. I asked him how he justified it to himself and his answer was fascinating. He told me he didn’t believe in truth. When I asked him to explain what he meant he couldn’t, which was strange because like most confidence men, he was highly intelligent and articulate.

But I learned other things along the way: The con artist doesn’t just want your love or your money, he wants your trust. Trust is what he’s after — at least for a time. The only way he can attain your trust is by fashioning himself into another person. Great conmen are experts at impersonation and reading the needs and wants of their victims. They become the person we want them to be. In seducing his victim, the conman is also, of course, gratifying himself. Through his victim’s eyes he can finally become someone else. This is his real goal, because for a brief time, he escapes himself.

This is what Ripley really wants. It’s the same thing the Frenchman in Toronto wanted. It is, I believe, what all conmen want. Not the money or the house or the clothes or the girl or the sailboat or the signet ring (there are other, less risky ways to get all those things). He wants escape his own suffering, but he can only do this by temporarily becoming someone else.

We all have a bit of Tom Ripley inside us. We all want release from time to time, but the conman yearns for it on a much deeper level. His emptiness is profound and desperate, a kind of roiling inner chaos. His habitual dishonesty isolates and alienates him, over time he finds it impossible to love. When you build all your close relationships on lies, this is inevitable. Your friendships and intimacies are compromised and eventually unravel. Ulimately forget who you are and what you want. So the conman does the only thing he knows how to do. He keeps on working the his scam until he’s found out — at which point he takes what he can and vanishes. Then the cycle begins again. I suppose there are conmen who give up lying, but I’ve never met one.

I came across an obscure blog post on LinkedIn (of all places) that described the appeal of Tom Ripley quite brilliantly:

…we all face moments in our lives when we get to choose how best to present ourselves. It’s particularly true when you’re papering over trauma. There are choices to make in such moments. Some involve omission. Some are edgier. Ripley always makes the most extreme version of the wrong choice. But for a moment you make it with him, and you're thrust out on a limb, treading water in mid-air.

Confidence men will always find victims, not because people are gormless and vain but because we are social animals, hardwired to trust. In order to live our lives we must accept that most of the people around us are operating according to the same basic rules. For example, everyone knows that there are drunk drivers and pedophiles in the world, and yet most of us commute to work and drop our children off at school without a second thought. We conduct our lives based on the understanding that most people endeavour to be honest and good most of the time, but some people just don’t.

When my conman acquaintance said he didn’t believe in truth, I suspect this is what he actually meant. In a way he was right. Collective ‘truth’ is a fiction, but so is pretty much everything in human culture. It’s perfectly normal for an intelligent person to query or reject the idea of ‘truth’ or ‘reality.’ Most of us do it in the socially sanctioned middle class way, by smoking too much hash and reading a bunch of French literary theory in undergrad. The difference with conmen is that they take this questioning one dangerous step further. They exploit other people’s belief in truth to their own advantage, and they do so repeatedly until it becomes second nature. This cycle of exploitation and the pattern of chaos it creates in the conman’s life then becomes his central preoccupation and purpose.

Conmen prey on the tender, selfless part of us. The open and honest part that, over time, they have cauterized and amputated from themselves. They leave good people wondering who we are and what we ought to believe. If you’ve ever been conned you’ll know it’s a gut-wrenching experience, as bewildering as falling in love and having your heart cruelly broken for logical reason or fault of your own. You move very quickly from loathing the conman to loathing yourself.

This is why, when we encounter a Tom Ripley in real life we continue to ponder him long after he has vanished into the night. It’s not because the conman is particularly complicated or interesting but because we understand he’s just like us, except with a key missing part: The ability to trust. He inserts a glass shard into our hearts and leaves it there as his parting gift. Just for a moment, we get to experience the horror of what it’s like to be like him.