BROOKE GLADSTONE: And I'm Brooke Gladstone. And this is Bernie Madoff talking about humanity’s instinctive tendency to be greedy.

BERNARD MADOFF: As honest as you can try and get people to be, there’s this normal, natural pull, you know, that you have to deal with.

BROOKE GLADSTONE: He was speaking at a public roundtable in 2007, explaining how computers and algorithms had cleansed his business dealings of that regrettable impulse. You know, words can't describe a guy like that. Well, actually, two words can, words that fit into a very long, very rich and very American cultural tradition. OTM producer Jamie York is here to tell us what those two words are.

JAMIE YORK: It’s not “monster,” although that’s the word New York Magazine used on last week’s cover, featuring him leering and made up like the Joker, nor is it “super-villain,” although it used that word, too. No, the words that best fit the man who operated what may be the largest Ponzi scheme in history is “confidence man.” He’s just the latest and greatest in a long line of American con men, so great he even stunned the famously jaded news media.

MALE CORRESPONDENT: All a lie. There were no trades, no stocks. All the money has disappeared.

MALE CORRESPONDENT: No investments for 13 years? I mean, so essentially if that is, in fact, true, all those statements he was sending out were just complete - fabrications.

FEMALE CORRESPONDENT: It’s amazing. I have to say when I first saw it today, I had to reread it a couple of times so it could really sink in.

MALE CORRESPONDENT: It now appears that even the world’s best-known Holocaust survivor didn't touch the conscience of Bernard Madoff.

JAMIE YORK: Con games are old, as old as trickery and fraud, but the United States has provided fertile ground for the art to grow and thrive. Luc Sante is a writer, often about history, crime and art.

LUC SANTE: The most famous original use of the term “confidence” in that way is in the title of The Confidence Man by Herman Melville. It proposes a certain kind of flimflam as being close to the heart of the national project.

JAMIE YORK: The 1857 novel was the last work of prose Melville published in his lifetime. It’s a story of steamship travelers heading down the Mississippi. It’s also a profoundly cynical examination of what made our fledgling nation tick.

STEPHEN MIHM: To a tee, every single one of his victims are people whose eyes light up as they see the riches before them, or the perceived riches, the illusory riches, and gladly give the confidence man what he needs, which is confidence, confidence that the confidence man will deliver.

JAMIE YORK: Stephen Mihm is a historian, and author of A Nation of Counterfeiters: Capitalists, Con Men and the Making of the United States. He says 1857 was the apex of a kind of financial chaos.

STEPHEN MIHM: The national government had effectively ceded control of the money supply to private banks, who got to issue paper money in quantities and designs, effectively, of their choosing. And, by the time 1857 rolled around, you had almost 10,000 kinds of money in circulation [LAUGHS], which, of course, was a crazy system. It was a system in which you really never knew what kind of currency someone was going to try to pay you with.

JAMIE YORK: Ten thousand different kinds of currency meant that nearly any financial transaction was based almost exclusively on faith, faith that was profoundly shaken anytime folks wanted real money for their dubious paper. Banks often didn't have it. And when confidence in the banking system collapsed, so did commerce, as everyone tried to unload as much useless currency as they could, onto each other. Mihm says it was every man for himself.

STEPHEN MIHM: Let's say that you’re a counterfeiter, which was the quintessential confidence man [LAUGHS] of the era. You would go in to a retailer and you would try to do everything in your power to convey the message that you were a good, respectable person. You would dress as nicely as you could, and you would fob off the bill onto them.

JAMIE YORK: But here’s the kicker. It’s not simply the staging of a little fraud that makes for this gateway to the confidence game, it’s the knowing complicity of the person being conned. That’s what makes them a mark.

STEPHEN MIHM: What’s fascinating is that if you were running a store and someone came in and paid with a counterfeit note you might know that it was a counterfeit note, but you would take it because it was a good counterfeit note, and you knew that you could pass it onto someone else. It didn't matter that it was counterfeit. It only mattered that it could pass.

[MUSIC UP AND UNDER]

JAMIE YORK: Maybe that’s when it started, when we first saw ourselves in the con man and the con man in ourselves. The con man was quintessentially American, geographically mobile, when we were all learning to ride the rails. Reinventing himself when this was the hope of every immigrant or city dweller. Succeeding by using his brain, not his connections, which was the definition of the American dream. Americans had been seduced by these qualities from the moment the con man became a fixture in the penny papers of the 1800s, and ever since, embodied over and over again on the silver screen. In the classical fictional con, we blame the victims because they're carefully selected – bankers, business tycoons, millionaires, crime bosses. Ordinary guys can't win against the fat cats, but, like James Cagney in the 1931 film, Blonde Crazy, con men help to even the score.

[CLIP FROM BLONDE CRAZY]:

JAMES CAGNEY PLAYING BERT: Honey, I'm Santa Claus, Robin Hood and the goose that laid the golden egg, all in one.

JOAN BLONDELL PLAYING ANN: Pretty big package, aren’t you?

JAMES CAGNEY PLAYING BERT: But seriously, Ann, there’s a lot of loose money lying around if you only know where to look for it. Now, the world owes me a living, and I'm going to collect it, see?

[END CLIP]

JAMIE YORK: The con preys on anyone who believes that you can get something for nothing, and it takes two key forms. Luc Sante.

LUC SANTE: A short con takes place in the course of a single meeting, and it takes what the victim has in his or her pockets.

JAMIE YORK: That’s the hardy perennial, the three-card monte game you think you’re just about to win, until you’re broke. In contrast -

LUC SANTE: A long con or a big con is a whole theatrical setup that takes place over a great span of time and always involves the victim going to get more money to invest in the scheme.

[CLIP FROM THE STING]:

ROBERT REDFORD AS JOHNNY HOOKER: I got a partner downtown -

[END CLIP]

JAMIE YORK: Robert Redford plays the long con on a mob boss in The Sting.

[CLIP – THE STING]:

ROBERT REDFORD AS JOHNNY HOOKER: - and he runs the central office of the Western Union. Now, race results from all over the country come in there and go right across his desk to the bookies. Now, all he does is hold them up for a couple of minutes ‘til he can call us, get a bet down on the winner. Then he releases the results to the bookies. We clean up on a race that’s already been run. Now, you can't miss, unless the Western Union dicks get a hold of it.

JAMIE YORK: The Sting is explicitly based on a seminal book published in 1940, David Maurer’s The Big Con, a scholarly work that reads like a novel. Maurer was a linguist, fascinated by the mechanics and the patter of the con. He spent years recording the inner workings of a loose tribe of professionals. He found that the long con separated a mark from his money exclusively through a kind of cerebral ju-jitsu, one in which the mark gives over his money, only because he wants to. There’s no force, no intimidation. This could take weeks, months, or [LAUGHS] in Madoff’s case, allegedly 13 years. Long con artists create phony stock offices, betting parlors or banks, and hire dozens of other disguised con men to act as ropers. It’s the brazenness of the con that pays off most, the iron fortitude required to risk detection and continue on. It demands a deep understanding of human behavior. It’s theater for an audience of one. Luc Sante says that it’s fitting that a linguist undertook this work because it’s the language that has seduced writers for the last 60 years.

LUC SANTE: The language has this particular snap, crackle and pop to it. The con is an area of American life that birthed an entire technical vocabulary, a very large one, as full of newly-created nouns and verbs as sailing, for example, the shipping trades. They have a particular sound to them. Well, you can hear it just in the names of the major cons: the wipe, the rag, the tap, the iron hat. They're short but they're elemental, and they're as weighted as poetry.

JAMIE YORK: Maurer’s book set a template for the con movie. Dozens of them use his color commentary as a blueprint. The con man became shorthand for a slippery charmer who was, in fact, a dirty rotten scoundrel.

[CLIP FROM DIRTY ROTTEN SCOUNDRELS]:

MICHAEL CAINE AS LAWRENCE JAMIESON: Freddy, the women I deal with are carefully screened. They're wealthy and corrupt. I never take advantage of the poor or the virtuous.

STEVE MARTIN AS FREDDY BENSON: All right, all right. We'll forget about the money –

MICHAEL CAINE AS LAWRENCE JAMIESON: Mm-hmm.

STEVE MARTIN AS FREDDY BENSON: - but the bet is still on. We'll think up a whole new bet.

MICHAEL CAINE AS LAWRENCE JAMIESON: All right. What is the bet?

STEVE MARTIN AS FREDDY BENSON: We'll make her the bet.

MICHAEL CAINE AS LAWRENCE JAMISON: What do you mean?

STEVE MARTIN AS FREDDY BENSON: What do you think I mean? The first one to get her into bed!

[END CLIP]

JAMIE YORK: When con men aren't preying on marks, they're inevitably going after – each other. In films as different as Blonde Crazy and Dirty Rotten Scoundrels, the confidence men are the last to realize that they themselves have been conned. We're led to believe that in the divine order, this is how crookedness regulates itself, that there’s little honor amongst – as in this film – Grifters.

[CLIP FROM THE GRIFTERS]:

ACTOR PLAYING OLD TIMER: A grifter’s got an irresistible urge to beat the guy who’s wise.

JOHN CUSACK AS ROY DILLON: There’s nothing to whippin’ a fool. Hell, fools were made to be whipped. But to take another pro, even your partner, who knows you and has his eye on you, that’s a score.

[END CLIP]

JAMIE YORK: But this is the movies, after all, so if there’s any single force that can act as an antidote to the con, it’s love, from The Music Man, to Paper Moon to, perhaps, the best example, 1941’s Preston Sturges film The Lady Eve, in which a mark, played by Henry Fonda, finds out that his lady, played by Barbara Stanwyck, is playing a con on him.

[CLIP FROM THE LADY EVE]:

[MUSIC UP AND UNDER]

BARBARA STANWYCK AS JEAN HARRINGTON: You see, Hopsy, you don't know very much about girls. The best ones aren't as good as you probably think they are, and the bad ones aren't as bad - not nearly as bad. So I suppose you’re right to worry, falling in love with an adventuress on the high seas.

HENRY FONDA AS CHARLES PIKE: Are you an adventuress?

BARBARA STANWYCK AS JEAN HARRINGTON: Of course I am, all women are. They have to be.

[END CLIP]

JAMIE YORK: The Lady Eve, in the end, is a very romantic movie about our illusions about one another, about the way we all deceive one another, especially in love relationships. David Edelstein is the film critic for New York Magazine and NPR’s Fresh Air.

DAVID EDELSTEIN: We have this infinite faith that if people are, indeed, preying on us that they all have the capacity to be transformed by love into opening up, into owning up, admitting their sins, confessing and rebuilding our trust in them.

[CLIP FROM THE LADY EVE]:

BARBARA STANWYCK AS JEAN HARRINGTON: You weren't thinking of taking him, Harry.

CHARLES COBURN AS ‘COLONEL’ HARRINGTON: Well, what were you thinking of?

BARBARA STANWYCK AS JEAN HARRINGTON: I don't think you understand, either of you. This is on the up and up. I – I think I'm in love with the poor fish. I am going to be exactly the way he thinks I am.

JAMIE YORK: The Lady Eve uses love to strike a balance in the con game. Crime doesn't totally pay and gullibility doesn't cost you everything. But there’s another film version of what the con says about American life. David Mamet, a repeated purveyor of the con, has made a number of films that Edelstein says have the same basic message.

DAVID EDELSTEIN: David Mamet lives by a certain credo, and that credo is there is always somebody out there who wants to screw you over.

[CLIP FROM HOUSE OF GAMES]:

JOE MANTEGNA AS MIKE: You’re not miffed at us, are ya? I mean, nothing personal.

ACTRESS: You guys were going to con me out of my money.

ACTOR: It was only business.

ACTOR: It was only business.

ACTRESS: It was only business, huh?

ACTOR: The American way.

[END CLIP]

DAVID EDELSTEIN: He sees all human relationships, especially relationships between male and female, as essentially cons. And David Mamet’s role is to turn this into an existential test for his heroes. If they are to grow and to succeed, they must understand that they cannot trust anything around them, unlike in The Lady Eve, where you really do feel as if there’s some compromise possible between one’s worst fears about human nature and one’s greatest hopes about human nature.

JAMIE YORK: The Lady Eve is a classic because its moral is one we want to be true, but it’s hard to hold onto when Mamet’s version of human nature seems to better reflect our real lives.

[CLIP]:

[MUSIC UP AND UNDER]

ACTRESS: So you can't cheat an honest man.

JOE MANTAGNA: That’s probably true. But what we've just seen is the operation of a slightly different philosophic principle.

ACTRESS: Which is?

JOE MANTAGNA: Don't trust nobody.

[END CLIP]

[MUSIC UP AND UNDER]

JAMIE YORK: His watch-your-back moral may have the most to teach us when the con is no longer an intimate negotiation but rather a systemic abstraction, like Madoff’s computerized trading or the subprime mortgage crisis. Maurer wrote in 1940 that:

MAN: “Confidence games are cyclic phenomena. They appear, rise to a peak of effectiveness, then drop into obscurity, but they have yet to disappear altogether. Sooner or later they are revived, refurbished to fit the times and used to trim some sucker who has never heard of them. Until human nature changes perceptibly, there is little possibility that there will be a shortage of marks for con games.”

GEORGE PACKER: A metaphor for Florida is that it’s a Ponzi scheme. It was - crazy.

JAMIE YORK: New Yorker staff writer George Packer traveled to the epicenter of the country’s housing crisis, where he found a Ponzi scheme writ large. In Florida, real estate had become the equivalent of the counterfeit bill from the 1850s that you took because you knew you could pass it, a rotten system that again made us complicit in our own undoing.

GEORGE PACKER: Ordinary people - secretaries, construction workers - were buying and selling multiple houses, speculating, flipping them. Real estate was everybody’s source of wealth. I saw some records that showed houses being flipped for double, overnight, literally. So it was unsustainable. It was a mirage.

JAMIE YORK: This was greed putting all of us pigeons in a fever, suspending our better judgment – not just Madoff investors or mortgage signees, but all of us.

GEORGE PACKER: Economically, Florida does hold a kind of funhouse mirror to the country and shows us something true about ourselves. We live on debt. We don't think in the long term. We imagine that wealth can be created by simple transactions that don't actually require [LAUGHS] a whole lot of work. We don't want the government involved in our economic affairs. We don't want to pay taxes to support the services we expect. And those are all qualities that are on full display in Florida.

JAMIE YORK: In all of the depictions of the con, from Jimmy Cagney to Paul Newman to Nicholas Cage, the drama hinges on a single moment – the reveal, when the con is exposed and the mark tries to make sense [LAUGHS] of what has gone wrong. Sometimes we're in on the finer points of the scheme, other times we're with the mark. It’s a 90-minute lesson we pay to puzzle out in the safe space of the theater, where we can be our better selves. But Bernie Madoff and his flock of pigeons are, of course, terribly real, and they tell us something about ourselves we might not want to know.

[CLIP FROM PAPER MOON]:

RYAN O’NEAL AS MOSES PRAY: I want you to promise me just one thing.

TATUM O’NEAL AS ADDIE LOGGINS: What, Mose?

RYAN O’NEAL AS MOSES PRAY: When you grow up, don't you be the kind of woman who goes around deceivin’ men.

[MUSIC UP AND UNDER] Promise me that.

TATUM O’NEAL AS ADDIE LOGGINS: I promise, Mose.

[END CLIP]

JAMIE YORK: That promise doesn't even hold until the end of the movie Paper Moon, and no amount of con depictions can prepare us for the real choices that confront us. In personal relationships, I do believe the Preston Sturges moral that love can defeat the natural impulse towards greed, but in the rest of life, where impenetrable financial system hold sway and accountability is absent, I think Mamet’s right; love plays no role, and the con never really goes away.

[MUSIC UP AND UNDER] For On the Media, I'm Jamie York.

PEETIE WHEATSTRAW: [SINGING] You talk about confidence. I'm a confidence man from my birth. You talk about confidence. I'm a confidence man from my birth. That’s one thing sure – ooh well, baby, I have the confidence of any woman lives on Earth. I got a woman take care of me. Yeah, she’s just only sweet 16. Yes, I got a woman take care of me. Yeah, she’s just only sweet 16. I never done a day’s work in my life. Ooh well, baby, I don't know even what work means.

[HARMONICA MUSIC/MUSIC UP AND UNDER]