The latest newsletter included this astonishing piece from Time that offers the reader a panoply of practical advice about stealing art. As a heist connoisseur, I was quickly taking notes — but one thing that surprised me was how much of the piece focused on emotions rather than monetary gain: “Taking on all this risk for an object you don’t like, Breitwieser said, is the mark of a fool.” Also: “Don’t come alone. You’ll need a trustworthy accomplice as lookout.” And reading that unlocked for me why so many of my favorite heist stories — Leverage, The Sting, Sneakers — involve feelings as much as finance.
The upfront fun of a con artist is the way they manipulate the social fabric. Prohibitive rules and unspoken undercurrents become navigational channels into locked spaces: Martin Bishop holding a cake and balloons so the guard has to open the security gate for him, Sophie Devereaux playing both a wealthy duchess and a nerdy art restorer to gain access to a locked gallery. It’s a game, a puzzle, a magic trick, and like all those things we automatically root for it to work.
But we also root for the con artist to get caught — not by the law, but by the social threads they so clearly understand. We want them to come to trust the partner they’re forced to work with, we want them to fall for the mark, to leave half the cash on the steps of the orphanage and get the real villain, the heartless villain, hauled away in cuffs. We’re always looking for the moment they start to see the con as a means of making people happy, rather than extracting wealth.
Because the real fantasy of the con artist with the heart of gold is that the social fabric is sticky: it will cling to you like a spider’s web even when you’re trying to use it for selfish ends. A fictional con artist may be an egotist, but rarely a cold and unrepentant narcissist: Thomas Crown types far outnumber the Tom Ripleys. Audiences like brilliant and charming liars because audiences like storytellers — but audiences are smart, and they know that anyone who’s a storyteller is going to eventually have to tell them something true. Even if it’s in spite of themselves. There’s going to come a moment when the con falls apart, when all the lies are exposed, when the real stakes become apparent.
The real stakes: We don’t want people to be alone. And we don’t want connection with other humans to be a weakness. I think it’s one reason why heists have really taken off in the past few years. Heist stories, broadly speaking, are about a world of broken rules and moral grey areas where people still find ways to do good, to fall in love, to help someone. It’s a world where emotional justice matters more than the mere black and white of the law. Punishments are avoided, cynicism goes unrewarded. The best heist stories end with freedom, with rightness, with joy.