Shortly before midnight on April 15th, Homer discovers he didn't do his annual taxes. In a rush, he fakes deductions and provides false information on his form. Soon, Homer is arrested for tax fraud. Homer strikes a deal: He'll work for the FBI for immunity from IRS prosection.

Homer successfully assists the FBI in foiling his co-worker Charlie's scheme against government officials. Pleased with his work, the bureau enlists Homer for a more important project. In 1945, on behalf of the U.S. government, Mr. Burns was supposed to deliver a trillion-dollar bill to postwar Europe for reconstruction. It never arrived. The FBI suspects Burns still has the bill and asks Homer to infiltrate his mansion to find it.

Homer makes it into Mr. Burns's home, and, after he mistakes Homer for a reporter from Collier's, Burns shows Homer the bill. The FBI immediately rushes in and arrests Burns, who loudly critisizes the government's taxation and spending policies. Burns's words reach Homer, and at the ladt moment, he snatches Burns from the FBI. Burns elists the help of Smithers, and, together with Homer, they flee the country in Burns's plane. Burns decide to land in Cuba and offer Castro the trillion-dollar bil in exchange for the country. When they meet with Castro, he tells them Cuba is not for sale, but asks if he can see the bill. Burns lets him have the bill for a moment, and when Burns asks for it back, it's gone.

Floating on a makeshift raft with Homer, Burns decides that they should return to the United States, saying that he'll merely bribe the jury when the government brings him to trial for handing over a trillion dollars to Cuba.