Ned Flanders is awakened by the sound of Springfield residents celebrating New Year’s Eve. He dutifully sets about preparing his income taxes, and puts them in the mail the next morning. The time shifts to April 15th, where the post office is now the scene of pandemonium. Kent Brockman files a news report from the scene, prompting Homer to realize he has only a short time left to file his returns. Rushing through the forms, he lists a series of phony deductions in hopes of lowering his taxes. Though Homer is successful in beating the midnight deadline, his returns land in the “audit” chute at the Internal Revenue Service offices.

Homer is questioned by FBI Agents Miller and Johnson. Fearing a possible prison sentence for lying on his returns, Homer agrees to wear a hidden wire in an effort to flush out citizens who break the law. He is shown a film detailing how President Truman sought to end the economic suffering of post-war Europe by delivering monetary relief in the form of a trillion dollar bill. The man entrusted with delivering the money was none other than Mr. Burns. The bill, however, vanished, and agents believe it is hidden somewhere in the Burns mansion. Homer sneaks inside the estate and engages Burns in conversation. Mistaking Homer for a Collier’s reporter, Burns gives Homer a tour of his home. Burns admits he opposes America’s spendthrift politicians, who would have squandered the money foolishly by giving it away. He shows Homer the real trillion dollar bill, prompting the agents to arrest him. But Burns gives an impassioned speech defending his action. Moved, Homer literally yanks the rug from beneath the agents, throws Burns over his shoulder and makes a getaway.

Homer, Burns and Smithers make their way to a nearby airport, where Burns takes command of his old aeroplane. Flying high above international waters, the threesome spot Cuba. Burns lands the plane on the island nation, and the men take a taxi to Castro’s Presidential Palace. Unbeknownst to them, Castro has concluded that communism is a complete failure and that it is time to surrender to Washington. Later, he tells the threesome his country is not for sale. He nonetheless asks to see the trillion dollar note—and then refuses to return it. Now penniless, Burns, Homer and Smithers use a tiny raft to sail back to the United States.