When Homer discovers that he was almost elected class president in high school, an old Italian cook uses a magic pot of tomato sauce to show him an alternate version of his life.

Townspeople gather at the Springfield Walk of Fame, where Mayor Quimby inducts the newest honoree: Vance Connor, a local businessman who was Homer and Marge’s class president in high school. A surly Homer tells Bart and Lisa that he ran against the popular Vance, but blew the election when he tried to ad lib an important speech to the student body. Marge assures Homer that his life turned out to be a happy one despite losing to Vance. Homer is convinced that behind the smile, Vance must be an unhappy man. When Homer approaches Vance to prove his suspicion, it becomes apparent that Vance really is a happy guy. Homer ends up at Moe’s bar, where he tells the barflies that Vance ruined his life. Lenny and Carl make a confession: while they were in high school, Principal Dondelinger instructed them to bury a ballot box. Homer realizes he may have won the election after all. One night Homer shows up at Lenny’s apartment, and demands to be shown where the ballot box is buried. Lenny escorts Homer into the woods, where the two of them do some digging. Once the box is unearthed, Homer carries it home. Lisa counts the ballots... and declares Homer the winner. She warns that despite what he may think, winning a high school election doesn’t mean his life would be any better. Homer decides to track down Dondelinger, and tell him about the discovery.

Homer finds Dondelinger on a golf course at a retirement community. Dondelinger admits he never liked Homer. It turns out, however, that Dondelinger uncovered a plot to get Homer elected class president as a joke; that way he would be humiliated all through high school and at every class reunion. Hoping to spare Homer emotional pain, Dondelinger had the ballot box buried. That night the Simpsons have dinner at Luigi’s Italian restaurant. Luigi tells Homer about an old man who works in his kitchen. If the Old Italian Man’s sauce is stirred in just the right way, it can reveal What Might Have Been. Homer observes as the boiling sauce shows him getting elected class president. The students cheer the news, as Homer is a loser just like them. In the present day Homer laments that he could have turned out to be a winner if fate had smiled on him instead of frowned.

The Old Italian Man again stirs the sauce, showing Homer and his family What Might Have Been. We see a teenaged Maude Flanders asking Homer if he has a date to the prom. It turns out Homer has his eyes on Debbie Pinson, a cheerleader. On prom night, as Homer dances with Debbie, he sees Marge dancing with Artie Ziff. Homer is stunned by Marge’s beauty. Thinking quickly, Homer gets Debbie to leave the room so he can ask Marge to dance. That night Homer escorts Marge home, where they kiss. Later Mr. Burns hires Homer to work at the power plant. The scene shifts back to Luigi’s restaurant in the current day. Lisa, who has been looking into the sauce, realizes that Homer’s life turned out the same whether he was elected class president or not. Then the Old Italian Man tosses more ingredients into the sauce, and the Things That Might Have Been continue. This time it becomes apparent that Homer and Marge never had children.

When Homer returns home, he mopes around the house and lays in Maggie’s inflatable baby pool. Marge and the kids decide to take Homer for a walk. They lead him to the Wall of Fame, which now features a photograph of Homer’s face. It reads: Homer Simpson—Class President Elect. Homer is thrilled. He thanks his family for their kindness.