Ready to Risk It All: Falling in Love with the Big Con

Robert Redford and Paul Newman in The Sting (1973) | art by Brianna Ashby
illustration by Brianna Ashby

When we first meet The Great Henry Gondorff, he isn’t really there. His landlady denies his existence; his door goes unanswered; his bed is empty. The enormous carousel that he mans stands unilluminated and silent, its parade of shadowy horses eerily lifeless. Johnny Hooker (Robert Redford), an aspiring grifter from the uninspiring streets of small-town Joliette, finally finds what remains of the great man wedged between the bed and the wall, fall-down-drunk and dead to the world. Johnny’s disgusted expression is the impotently resentful mien of a mark inopportunely seeing through a scam, and it speaks for us all: we’ve been promised the best inside man alive, a connoisseur of the reverently whispered, always capitalized Big Con—so where is he?

Superficially, Gondorff (Paul Newman) has retreated into this state of diminishment out of necessity, driven into hiding after falling afoul of law enforcement. However, it’s not fear of the g-men that has him drunkenly hiding under his bed: the real root of his malaise, we find out much later, is far more spiritual. At some point during his time spent cleaning up in the city, gulling a mark a day, the unthinkable has happened—he’s fallen out of love with the Big Con. “The fix was in, dicks took their end without a beef; we had it down to a business,” he tells Johnny, “and it really stunk, kid. There’s no sense being a grifter if it’s the same as being a citizen.” Yes, he was chafing against the demanding schedule, the mass-production deception, but his dissatisfaction runs deeper. It had become too easy, too comfortable. The stakes just weren’t there anymore. Chicago is a rigged city, and where’s the rush when you know you’re going to win?

And so, this is how our two protagonists stand at the beginning of the con that makes up the bulk of the plot of George Roy Hill’s 1973 smash-hit The Sting: one sullen and sceptical, the other drunk and disillusioned. It’s not a particularly auspicious start, but fortunately this state of affairs is short-lived. All it takes is an outrageously dangerous proposal from Johnny and Gondorff’s feeling the old appeal, Newman smiling like he’s selling salad-dressing, his eyes at their most twinkly. He’s about to fall back in love with the risks and rewards of the Big Con, taking Johnny (and us) along for the ride. The carousel starts—lights flashing, horses dancing, jaunty music jangling—the flag is up, and we’re off and running.


It’s not as though we, the audience, need much encouragement; our collective love affair with scams and swindles is well documented and enduring. The apparent cultural fascination with the figure of the grifter that helped to make The Sting a runaway box-office smash in 1973 (or, more recently, had readers devouring evermore detailed dissections of the exploits of real-life scammers Anna Delvey and Elizabeth Holmes) is merely symptomatic of a far more ancient literary tradition. In Fast Talk and Flush Times, his influential study of the con-man as a literary convention, William Lenz identified the grifter as but an off-shoot, a “distinctly American version” of the pervasive trickster archetype, the character that boasts among its ranks figures as ancient and far-flung as Loki, Br’er Rabbit, Coyote, Anansi, Odysseus, and the Monkey King, to name but a fraction. Since we started telling stories, it seems, we’ve been telling stories about storytellers. But why do we find these fraudsters so appealing when, presumably, very few of us actually enjoy being defrauded?

To a certain extent, it is simply the thrill of a privileged perspective: grifter narratives tend to take us backstage, letting us poke around in the machinery of the scam and see how everything fits together. This not only allows us to admire the complexity (or, occasionally, the astonishing simplicity) of the grift, it also allows us to feel as though we are being both included and educated—not only are we in on the joke, we now know how to pull it off for ourselves. Maybe we don’t watch The Sting and immediately start running the wire on a local mob boss, but surely everyone that watches Redford outwit his pursuers by hitching a lift on that bin lorry thinks, however hypothetically, so that’s how I’d do it. This is why grifter narratives thrive on detail: we want to see, to study, every component of the metaphorical, or in some cases literal machinery (see the Rube Goldberg-esque device upon which Ferris Beuller’s Big Con relies). It’s not enough to know that Frank Abagnale passed Pan Am payroll checks by forging their logo, we need to see the toy aeroplanes soaking in his bathtub.

Hill is acutely aware of the appeal of this kind of minute, granular detail: for a film that essentially centers on deception and theft, The Sting is eminently generous. With one notable exception, we are party to every step of the process, from the bravura to the mundane. We are not only shown how the wire—the integral part of the con that allows them to retrospectively “rig” horse races—works, we also see the acquisition and even the refurbishment of the basement bookies that houses it, down to haggling over rent and arranging the transportation of furniture. It’s gloriously finicky, every detail on display: “How d’you wanna work this,” dapper hustler Kid Twist asks the props guy, “percentage or flat rate?”

Even when we don’t, or can’t, appreciate it, Hill and screenwriter David S. Ward are lavishing us with detail. The big twists are not telegraphed by any stretch of the imagination, but they are thoroughly contextualized. On a first watch, everything we hear about mysterious hit-person Salino seems like so much set-dressing: the late-stage revelation of their identity shines a new light on events, and that background noise suddenly becomes a step-by-step explanation of a certain character’s previously inscrutable actions. Similarly, a seemingly throwaway shot of Johnny stashing away an unidentifiable something ahead of the final “sting” sets-up the climactic twist; only once the dust has settled do we realize that we actually saw him insert the blood capsule that would allow him to fake his own death in the next scene. This clarity is testament to Hill’s commitment to visual storytelling and intelligent design. He consistently fills the frame with the kind of pertinent detail that, some 40 years later, Guillermo del Toro would denominate “eye-protein,” as opposed to “eye-candy”rather than decorative but empty calories, every detail is deliberately imbued with narrative significance. This narrative feast hooks us in, making us feel like part of the team. As a result, even when The Sting’s climax makes marks of us, it does so with such transparency that we walk away feeling not foolish but wiser.

Of course, this commitment to showing process isn’t unique to grifter narratives—one need look no further than Redford’s own career to see another celebrated example of a process film. Alan Pakula’s All the President’s Men, the archetypal newsroom film, approaches the legwork behind the breaking of the Watergate scandal with a similar reverence for the methodical. We see every phone-call, every scribbled note, every session sifting through library records, depicted with an almost obsessive respect for detail. The process becomes the point: Nixon’s resignation—the earth-shaking fallout of the information Woodward (Redford) and Bernstein (Dustin Hoffman) have spent the better part of the last two hours acquiring—is shown only in writing, in the very final shot, just as Gondorff and Hooker’s climactic “sting” lasts all of 10 minutes.

There’s one integral difference between these two process pictures, however, that illuminates the other secret of The Sting’s success. Pakula is dedicated to making his process look hard: his journalists sweat, swear, and chain smoke. They run headfirst time and time again into the brick walls of uncooperative sources and skeptical colleagues, bravely suffering several mini-martyrdoms in the service of truth and justice. For Hill’s band of liars and cheats, it’s an entirely different story. While he never shies away from detailing the practical work involved in running a con, the hard graft beneath the surface of a grift, his characters never make it look like a slog. Even when Redford is outrunning an armed policeman, there’s a spring in his step and ragtime in the air. And herein lies part of the answer to the question that has so unsettled Gondorff: what makes the work of grifter so different from the work of a citizen? Put simply, grifters have more fun.


If the painstaking depiction of the practical work behind a scam is the hook that involves us—makes us think, however hypothetically, I could do that—then it’s this glamorous sheen of laughing exhilaration that cements that attraction, makes us think, however hypothetically, I want to do that. The sheer enjoyment of pulling off a con, any con, is palpable. Even the relatively unsophisticated “pigeon drop” of the opening scenes thrills Johnny and his partner Luther (Robert Earl Jones), leaving them breathless and laughing. It’s more than the satisfaction of a job competently done: it’s the exultation of winning a game. And the Big Con is a game. Despite all the meticulous work that goes into it, there’s that one ineffable aspect of chance, risk, luck involved that transforms work to play, and simple success to victory.

This intersection between work and play is consistently probed by Ward’s screenplay. The language of the grifters is littered with phrases that complicate the two—“played the switch,” “play it on the fly,” “you think my play is bad?” In the life of a citizen, there is no such scope for overlap. Near the beginning of the film, we see Crystal, a friend of Johnny’s, hard at work onstage, her face painted with a performer’s smile and giving every indication of having the time of her life: the minute she exits the stage, however, the façade is dropped and she immediately starts airing work grievances. “For Christ’s sake,” she complains, “did you hear that out there? He dropped four beats in the middle of my goddamn routine! Now how long am I gonna put up with that?”

This little episode provides a neat contrast to the performances that Johnny goes on to give later, once he’s firmly enmeshed in the Big Con. At one point, he and Gondorff fake a tiff for the benefit of their mark, Henry hitting him with an icy glare and a dismissive “Don’t give me any of your lip, kid.” Where Crystal smiles onstage and is miserable in the wings, Johnny and Henry fake a frown and are grinning with exhilaration the second their audience has left the room. It’s an eminently appealing image: they’re essentially the embodiment of the “find a job you love and never work a day” sentiment to which we’re all supposed to aspire. It just so happens that the job they love isn’t entirely legal.

That is not to say that it is simply a matter of legality, or lack thereof, that lends grifting its glamour. Alongside the distinction between grifter and citizen, the film makes another important comparison between our imaginative, sympathetic con men and another kind of ploddingly brutal criminality, represented by the mark, Doyle Lonnegan (Robert Shaw). He has none of the enticing glamour of Gondorff’s gang, not only because of he killed Johnny’s partner, Luther—an irredeemable act of violence that puts him in the gang’s sights—but also because his worldview is antithetical to the thrill-seeking reverence for risk that the grifters share.

He owns half the politicians in New York and Chicago and runs his criminal operations with complete impunity. He only employs people he can bully: his catchphrase is “You follow?” and they always do. He scorns games of chance, won’t bet on boxing and “never plays anything he can’t win.” When he plays poker, he cheats. And the result of all this is that he’s not just a violent murderer, he’s also inveterately dull. He’s the problem with grifting in Chicago, the kind of grand-scale rigging that Henry detests, personified.

His role as a mark is the essential difference between the menial grinding that originally broke Henry and the genuinely, joyously risky Big Con that we get to see: Chicago might be a rigged town, but it’s rigged in Lonnegan’s favor and this time Henry and his gang are taking on the city itself. The first showdown, where they square off at poker, provides a microcosmic demonstration of this. By turning up and cheating at a rigged table, Henry transforms Lonnegan’s moneymaking machine back into a battle of wits, reintroducing the element of risk and uncertainty that makes grifting a game, rather than a grind. Contrary to one member of the team’s confident assertion that all he needs to do is “show up with a lot of money and look like a sucker,” Henry reminds us that this time round his victory is by no means a forgone conclusion: “I’ve also got to win.”


And, naturally, he does win, in part because his complacent opponent has no idea that they are playing. Lonnegan is still operating as though the world around him is as he has always known it to be—under his control—when in fact, by inadvertently inviting a trickster to his table, he’s opened a doorway to a very different world indeed, one defined by risk and uncertainty. According to cultural anthropologist Victor Turner, this uncertainty that tricksters always usher into a narrative stems from their status as “liminal entities,” When a grifter spins a yarn for a mark, they are operating on a boundary between the regular world and a world of their own making, where the accepted rules of reality do not necessarily apply—a world in which you, lucky you, can own the Brooklyn Bridge, or predict the lottery numbers, or beat the ponies every time. In The Sting, this metaphorical liminality is literally reflected in the transient venues of the various cons—the basement bar set up in a couple of days, where nothing is as it seems, or the Western Union office that a exists for less than 10 minutes, leaving only mysterious green paint behind.  

These spaces give us a glimpse into another world where anything is possible—the perfect venue for a gang of outsiders to wrest away the control of a seemingly untouchable big-shot and, with dedication and a little bit of luck, beat him. It’s a pretty enticing vision, particularly in comparison with the “real” world that surrounds it. The film effectively takes place in two discrete realities, existing side by side, and Hill makes sure to reinforce the distinction between them, the grifters’ shiny world of play and possibility versus the depressingly familiar world of poverty and brutality where bullies like Lonnegan thrive.

The Sting opens, for instance, on a shot of one of Lonnegan’s minions striding past a row of dispossessed victims of the Depression, starving while he gets rich. This is a world order that everyone can instantly recognize, after all, as Hooker puts it, “There’s always a depression on.” We’ve all been Crystal, asking plaintively, “How long am I gonna put up with that?”—that work we don’t enjoy, those hours we can’t sustain, the co-workers we can’t stand—all the while knowing that we’ll be putting up with it for as long as we possibly can. Crystal can’t leave: she needs the five bucks.

Henry and Johnny, on the other hand, walk away from their work with nothing but a new partner and newly-discovered love for the Big Con, not bothering to pick up their share of half a million. In comparison with Crystal’s recognizably miserable pragmatism, this utopian vision offered by the enticingly ludic world of The Sting shines all the brighter because of, rather than in spite of, its incompatibility with our own lives. Being shut out only makes us more eager to vicariously visit this other world of possibility—where work can be play, the powerless can defeat the powerful, and even death is robbed of its authority. In the world of the Big Con, our hero can even take a bullet in the back and still come up smiling through his mouthful of blood. What’s not to love?