I found their scheme—swapping Winthorpe and Valentine to see if people are a product of their environment and circumstance, rather than innate character and abilities—not only the most insane social experiment I’ve ever heard of, but largely rooted in the culture of poverty theory, the idea, popular among some academics at the time, that people who grow up in poverty adopt certain values and behavior that keeps them impoverished. (It fell out of intellectual fashion for victim-blaming and not matching empirical data, but apparently it’s made a comeback in recent years.)
Ultimately, the Dukes are proven “correct” in their assumption that American inequality can be explained by a culture of poverty: Winthorpe, who went to Exeter and Harvard, when placed in the “worst social circumstance”—which to the Dukes meant being framed for a crime (aside: what kind of boss plants PCP on his employee?!), being jailed briefly, losing all of one’s physical property, social capital, and livelihood—becomes an antisocial criminal. That was pretty offensive.
But the opposite is perhaps equally as bad: Valentine—whom the Dukes deem to be from a “culturally disadvantaged” background that led him to a life of crime—becomes an elite when he’s given all the trappings of an upper-class American. Valentine even has impostor syndrome for a moment, where he’s really not sure people will buy it. To add to the perception of respectability, the Dukes start calling Valentine William instead of Billy, and they make him wear Winthorpe’s Harvard sports coat—clear signifiers that he’s an elite.
White: The idea that money was the cure to all the issues inherent to a lifetime of poverty or that all people, divested of their money and status would become violent criminals was, yet again, gross. It was all made worse that the bet was essentially just for bragging rights, showing how little the Dukes value human life. But luckily it all felt pretty fantastical, and so did the solution when Winthorpe and Valentine find out that they are both being played by the Dukes.
Winthorpe and Valentine learn that the Dukes were going to get the inside scoop on the orange juice contracts—the Dukes already bribed the person tasked with keeping the Department of Agriculture report about how orange crops were doing to give them the report a full day before it was released publicly. This allowed them to engage in a bit of insider trading and make a mint. Valentine and Winthorpe’s insane solution is to get even, replacing the report with a false one and then heading the commodities exchange to engage in some insider trading of their own, front-running the Dukes.
Lam: John Landis, the director, says they used real commodities traders as extras in that scene, and that it took him a lot of studying to understand Winthorpe and Valentine’s con. Basically the Dukes are insider trading, and Winthorpe and Valentine front-run them by first agreeing to sell FCOJ in April at $142 (an artificially inflated price, the product of the Dukes’ trying to corner the market), but the other brokers buy their contracts because they think prices will be even higher in the future, so it’s a deal. Once those contracts are set, Winthorpe and Valentine wait for the price to bottom out after the crop report comes out saying that oranges are doing just fine. Once the price drops to $29, they buy FCOJ futures at that price to fulfill the $142 contracts—so they win big.