Yearning for his lost youth and innocence, Mr. Burns searches for his beloved childhood teddy bear, Bobo. When Maggie comes across the bear, she claims it as her own. Mr. Burns tries to get his Bobo back by any means necessary.
One night, Burns is restless and has dreams of his old teddy bear, Bobo, who he foolishly abandoned as a child. Smithers overhears Burns in the night, discovering that Burns longs for his lost bear. The following day, it is Burns' birthday and the town is invited. He is offered gold, a unicorn, rings and even a performance by The Ramones. Burns is unsatisfied with his presents, and Smithers points out that Burns misses his teddy bear. Desperate to know what happened to his long lost bear, it turns out that Bobo was owned by Charles Lindbergh and Adolf Hitler. As of 1957, Bobo was washed up to the Nautilus submarine and discovered by Ice Deliverers in 1993.
The Ice Deliverers bring the ice to the Kwik-E-Mart, and Bart finds Bobo in an ice bag which Apu claims to be full of Heady goodness. Bart brings it home and gives it to Maggie. Homer is initially ignorant of the valuable bear being two feet in front of him when it is first shown on TV but he soon realizes its true identity. Homer intends on giving the bear to Burns in return for millions of dollars and three islands, but when he sees that Maggie will miss the bear, as well as Burns' reluctance in giving away the reward money he promised, he keeps it instead. To make matters worse, Burns goes on television to ask for his bear, and even cuts off the beer and TV supply in Springfield. Barney immediately goes to the house to threaten Homer with a gun, only for Homer to slam the door on him. Barney's gun goes off, followed immediately by the sound of glass breaking and a woman screaming. Police sirens are heard and Barney says "Uh-oh". The neighborhood forces Homer to give Bobo back, but when they see Maggie's expression, they turn it over to her.
Later, Burns is finally forced to confront Maggie in person, and convinces her to give him back Bobo. She does so, but the family does not get any gifts of esteem. That night, Mr. Burns snuggles up with his bear, wondering what the future will hold for it.
In 1,000,000 A.D., Bobo is found under a pile of rocks, by several apes. A robotic Burns snatches the bear and runs off, while being followed by Smithers, who has been turned into a robotic dog.