After the death of great aunt Hortense, the Simpson family attends a will reading. Each member of the family discovers they will receive $100 to do with as they like, but only after spending the night in a haunted house (which is surprisingly pleasant). Though Bart wishes to buy a hundred tacos from the TacoMat and Lisa to contribute to the Corporation for Public Broadcasting, Marge has them open bank accounts at the Bank of Springfield. Bart is excited with his new checking account, and begins writing checks for his friends.
Bart attempts to get Krusty the Clown's autograph, but Krusty is having a new sandwich named after him and has to leave. Just before he does, Bart slips a check for twenty-five cents into Krusty's pocket, figuring that he will receive a copy of it endorsed with Krusty's signature with his monthly bank statement. However, when Bart receives the check, it is endorsed with a stamp ("Cayman Islands Off-Shore Holding Corporation") instead of a signature; dismayed, Bart takes the check back to the bank so that they can force Krusty to sign it. The bank teller informs Bart that stamping the back of a check is perfectly legal, but becomes suspicious after analyzing the stamp and excuses himself to make a phone call. A chain of phone calls between different bank offices ensue, that eventually leads to an offshore bank in the Caymane Islands, where the bank official accidentally exposes Krusty's secret account. Five minutes later, Krusty is arrested for tax evasion, though Bart is not made aware of this for several hours.
The IRS takes control of Krusty's assets and his show (renaming it Herschel Krustofsky's Clown-Related Entertainment Show and turning Krusty Burger into IRS Burger, with meals named with tax-related terms and a six-to-eight-week wait to the customers, who apparently must report their income with every order as Homer asked Marge how much she lost on gambling), reducing his lifestyle to that of an average citizen. On top of that, his house and belongings are auctioned out for pitiful amounts of money, doing little to alleviate his tax debt. One evening, as the town watches, a depressed Krusty pilots his airplane into a mountainside. He is later pronounced dead.
A memorial service is held for Krusty at which Bob Newhart (who was actually there for a different funeral) offers condolences. While everyone assumes that Krusty is dead, Bart believes otherwise when he begins to see a Krusty look-alike all over town. With Lisa's help, he soon discovers that Krusty has gone into hiding under the disguise of Rory B. Bellows, a grizzled old longshore worker. With Krusty leaving on a boat heading for the ocean, they manages to convince him that fame is better than being a blue-collar worker, because it means that he will get more respect than every intellectual who has ever looked down on his show combined. However, Krusty had insured the life of his pseudonym and rigged his boat with explosives; returning to shore with Bart and Lisa, "Bellows"'s boat explodes, allowing Krusty to collect the insurance cash and end his tax woes.