After Homer and the family inherit some money from his late Great Aunt Hortense upon meeting the stipulation of spending the night in a "haunted" house, Marge asks the kids what they want to spend their money on. However, when Bart intends to take advantage of a Taco Hut deal (100 tacos for $100) and Lisa says she'll contribute her inheritance to the Corporation for Public Broadcasting, Marge puts her foot down and forces them to put their money in a bank account. Bart gets a checkbook that links into his account and starts writing checks to people, and in hopes of getting Krusty the Clown's signature, slips a check into his pocket. When his monthly bank statement comes in, he is upset to find that Krusty has neglected to sign the check, and instead the stamp of a holding company is present.
Bart goes to the bank but is informed that there is nothing wrong with simply stamping the check. However, the stamp makes the teller suspicious. The teller asks to be excused, and within a few hours (with Bart standing waiting for the teller to return), comes back to tell Bart that the check has caused Krusty to be arrested for tax fraud. It was revealed that Krusty is one of the biggest tax cheats in history, and that money was being held in an illegal account in the Cayman Islands (with no small help to the accounts manager saying he couldn't talk about Krusty's "secret illegal account" and thus unwittingly admitting it existed).
To pay for his tax evasion, Krusty's salary will be reduced drastically. The repayment eats into all corners of his empire. The Krusty the Clown Show is scaled back drastically (no money exists in the budget for props, costumes or Sideshow Mel), the IRS takes over ownership of the Krusty Burger chain, and Krusty's valuables are auctioned off.
Shortly afterward, Krusty is seen flying his private plane erratically, causing it to crash. When no remains are found, Krusty is declared dead. Bart is wracked with guilt, feeling terrible that he brought on the death of his idol. However, over the next couple of days, Bart is shocked when he sees a man looking suspiciously like Krusty. With Lisa's help, they soon find out that Krusty had faked his death, and assumed the new identity of Rory B. Bellows. Confronting him at the Springfield Docks, Krusty claims he is happy being a salvager, but Bart and Lisa convince him otherwise.
Krusty decides to give up his new life, and assures the two that with the life insurance from his identity of Rory Bellows, he should be able to pay off the government (he then blows up the boat they have just left).