The Simpsons abandon their attempts to go camping when bugs take over a park. Later, they happen upon a Native American gambling casino. As minors are not allowed inside the building, Bart is turned way. Undeterred, he sneaks inside by pretending to be ventriloquist Arthur Crandall’s dummy, Gabbo.

Unfortunately, Bart ends up being pulled away by casino guards and ends up in the Native American casino manager’s office. The manager warns Bart that unless he changes his deceitful ways, he will end up a bitter failure. The manager sprinkles some powder into a fireplace. He then shows Bart a look at his adult life, some thirty years into the future.

The story picks up in a beach bungalow, where a 40-ish Bart lives with Ralph Wiggum. Things begin looking up when Bart receives an invitation for his band to perform at Nelson’s nightclub. First, however, Bart must get his amplifier out of hock. Bart ends up borrowing money from a now-blind Milhouse.

Soon after, Bart and the band take the stage at Nelson’s Crab Shack. But when Bart announces his intention to perform a Jimmy Buffett song with altered lyrics, the crowd boos the band off the stage. Just when all looks hopeless, Bart discovers that Lisa has been elected president. Bart decides to pay his sister a visit in Washington…and brings a borrowing sack along with him for good measure.

When he arrives at the White House, Lisa is dealing with a crisis:the United States is bankrupt. At Marge’s insistence, an exasperated Lisa allows her brother to stay. Unfortunately, Bart’s very presence proves disruptive, and on top of the pressing financial crisis, Lisa must deal with his nonstop shenanigans. As Lisa prepares to give a televised speech that could make or break her presidency, Bart asks her to play his demo tape in the background.Lisa responds by shoving the boombox off her desk, sending it crashing to the floor.

Moments later, Lisa addresses the cameras and announces her "temporary refund adjustment." At first, viewers respond good-naturedly to the sweet-sounding"refund adjustment"…until Bart strolls into frame and reveals that it is really a tax increase.

Meanwhile, Homer sets out to find Abraham Lincoln’s buried gold, something Lisa assures her father is a myth. Americans voice their displeasure with the idea of a tax hike, prompting Lisa to wonder where the money will come from to pay off foreign debt. Lisa decides an international economic summit is in order. She instructs her security advisor to keep Bart out of her hair, fearing his meddling could trigger another debacle.

Lisa then appoints Bart the "Secretary Of Keeping It Real." As his first assignment, he is to go to Camp David with his friends and author a report that will change her from a nerd to "one cool bird." flattered Bart embraces the offer. While at Camp David, Bart and Ralph decide to get some coffee. When they reach the front gate, however, they encounter Chief Wiggum, who reveals he is under order to keep them at Camp David until the economic summit ends.

Bart interrupts the summit and puts his highly-developed mooching skills to work by tricking the foreign lenders into believing that their payment checks are in the mail.Lisa thanks her brother for buying the country more time to come up with the money.

Meanwhile, Marge discovers a parchment containing a handwritten message from Abraham Lincoln…only to realize that the gold rumors were actually a metaphor for what is "in the heart of every freedom-loving American." When the glimpse into the future ends, the casino manager tells Bart that if he wishes to change his destiny, he need only jump up and touch the ceiling three times. Bart does this twice…but then tires and quits.