Series premiere. 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.
Hoping to unmask the mysterious “Uncle Jerry,” the FBI investigates two prominent figures they believe are connected to the scam. The first, Jerome “Jerry” Jacobson, is a former cop who works security for Simon Marketing, the company hired to run the McDonald’s Monopoly game. The second, Gennaro “Jerry” Colombo, hails from a notorious East Coast mob family and is no stranger to unsavory activities.
Meanwhile, Agent Mathews and McDonald’s employee Amy Murray team up once again to pay a visit to prior winner, Buddy Fisher, who sweats and mumbles through his story about “winning” a million dollars as their cameras are rolling.
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.
A car accident lands Gennaro "Jerry" Colombo in the ICU, leading Jerome "Jerry" Jacobson to scout for new recruiters. Among those who join the operation are ex-con Andrew Glomb and Mormon real estate developer Dwight Baker, who convinces his foster son George Chandler to redeem a winning ticket.
With "Operation: Final Answer" gaining speed, the FBI gathers intel on "Uncle Jerry's" middlemen and ends up tailing Dwight to the airport, where they worry a family confrontation may turn violent.
Focusing their attention on Dwight Baker, the FBI intercepts a call with "Uncle Jerry" that leads them to capture crucial evidence of a game piece exchange. With the latest Monopoly game drawing to an end, the FBI works overtime to launch a coordinated cross-country day of indictments, though a last-minute technical error threatens to upend their carefully-laid plans.
As the conspiracy becomes front-page news and those charged deal with the fallout, questions remain about how Jerome "Jerry" Jacobson actually got ahold of the Monopoly game pieces and who was the person who tipped off the FBI with that initial phone call.
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.