After the family's Great-Aunt Hortense passes away, the family is given the stipulation to spend one night in a haunted house to collect her inheritance to them...which comes out to $100 for each of them.
Lisa and Bart want to spend their money, but Marge forces the kids to put their money in the bank. While Lisa opens a savings account, Bart opts for a checking account. Hoping to get Krusty the Clown's autograph, he slips a check into the clown's pocket, waiting for the check to return, cashed with Krusty's signature. However, the check returns with a stamp for a holding company in the Cayman Islands.
Bart takes the check to the bank demanding they make Krusty sign it. However, the bank soon gets suspicious of the stamp, and in the course of several hours, Krusty is found to have been evading paying the IRS for many years.
After being arrested, Krusty's entertainment empire is financially set upon as the IRS takes control of everything from his television show to the Krustyburger restaurant chain. Even Krusty's mansion and valuables are auctioned off.
The town is then treated to a grisly sight as Krusty flies his private airplane into a cliffside, where it explodes in a huge fireball. Finding no remains, it is assumed that Krusty is now dead. Bart is overcome with grief that he was responsible for the death of his hero, but is shocked when he notices a blue-haired man about town in several places. Something about him seems familiar, and Bart soon recruits Lisa to help him find out more about the strange man.
Their investigation leads them down to the docks. Inquiring to Captain McCallister, they find a wall of checks with the names of people whom not to do service with. One of the checks is signed with the name Rory B Bellows, and has stars drawn on it, similar to Krusty's signature.
The two use the check to track down Rory to where his boat is. At first denying it, Rory soon admits that he is Krusty. Apparently, Krusty faked his death in hopes to get out of owing the IRS further back payments.
Krusty claims he's fine salvaging sunken barges for scrap iron, but Bart and Lisa soon get him to admit that he enjoys being an entertainer, and Krusty adopts his former look. As Bart and Lisa walk off with Krusty, Bart asks how he'll get out of paying his backtaxes to the IRS. Krusty assures Bart that 'the life of Rory B Bellows is insured for a surprisingly large amount.' A few seconds later, Krusty's boat explodes, and the 3 walk off, laughing amid the falling debris.