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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, but George Chandler and others try to prove their innocence. When a previously uncooperative Jerome "Jerry" Jacobson takes the stand, the remaining details of the scheme are disclosed. Almost twenty years later, those involved reflect on what they learned, their regrets and the ripple effects of one man's greed.