In 2001, FBI Agent Doug Mathews of the Jacksonville, FL branch clocks an intriguing post-it note that piques his interest. The anonymous tip speaks of a con surrounding the much-beloved McDonald's Monopoly game and a mysterious mastermind behind it all: a man going by the moniker of "Uncle Jerry." With the help of McDonald's employee Amy Murray, the investigation, codenamed "Operation Final Answer," prompts Agent Mathews to propose an unorthodox undercover sting involving a video production crew. The operation tests nerves but leads to an early breakthrough in what promises to be a bizarre but unforgettable case.

Frank Colombo, the brother of Gennaro "Jerry" Colombo, reveals the inner workings of the scam whereby "Uncle Jerry" would sell the winning tickets to his brother for a premium. Colombo would then find willing takers for the game tickets in exchange for a cut of the prize money. Robin Colombo shares more about the recruitment operation and details the night when she and Jerry Colombo went for a car ride and faced sudden danger. Meanwhile, under the pretense of organizing a reunion for past winners, the undercover FBI video crew interviews Gloria Brown, a single mom and million-dollar "winner" in South Carolina, who tries to obscure her past in Jacksonville and the origins of her winning game ticket.