An anonymous tip to FBI agent Doug Mathews speaks of a con surrounding the much-beloved McDonald's Monopoly game and its mysterious mastermind, a man going by the moniker of “Uncle Jerry.”

Hoping to unmask “Uncle Jerry,” the FBI investigates two prominent figures they believe are connected to the scam; Agent Mathews and McDonald's employee Amy Murray pay a visit to a prior winner, who sweats and mumbles as their cameras roll.

Frank Colombo reveals how “Uncle Jerry” would sell the winning tickets to his brother, Gennaro “Jerry” Colombo, for a premium. The undercover FBI video crew interviews a winner who tries to obscure the origins of her million-dollar game ticket.

Gennaro "Jerry" Colombo lands in the ICU, leading Jerome "Jerry" Jacobson to scout for new recruiters. Dwight Baker and others join the operation. The FBI gathers evidence.

Focusing their attention on Dwight Baker, the FBI intercepts a call with "Uncle Jerry" that leads them to capture evidence of a game piece exchange; the FBI works overtime to launch a coordinated cross-country day of indictments.

As the trial nears, many of the defendants take plea deals and cooperate with the government, but George Chandler and a handful of others decide to fight to prove their innocence. When a previously uncooperative Jerome "Jerry" Jacobson takes the stand, the remaining details of how he pulled off his scheme are disclosed. Almost twenty years later, new information is revealed, and those involved – from "winners," to co-conspirators, to family members and government officials – reflect on what they learned, their regrets and the ripple effects that one man's greed had on so many people nationwide.