Tim and Stu win a game of pool at O'Flaherty's, and their opponent - a self-described hustler named Gabe - reneges on his bet, leaving Tim in the lurch for $190. At home, Amy nags Tim to go shake the hustler down for the money owed. The next day, Tim goes to the school where Gabe teaches math. When he tells the principal about the gambling debt, the administrator doesn't care, but it soon comes out that Gabe has been having sex with one of his students at Quizno's, which is a problem. After Gabe gets fired, he takes Tim and Stu to the horse track, where they place a long-odds bets on Nagging Blonde. But the "hot tip" that led Gabe there turns out to be his family's ploy to stage a compulsive-gambling intervention ... at the track. As Gabe's family confronts him about his problem, Nagging Blond wins the race - pulling in $10,000. That night, Tim takes Amy to dinner, explaining how a horse that reminded him of her won them so much money. She's thrilled ... until he tells her the animal's name.
Tim and Stu meet some political chicks, who are protesting the circus as it arrives in Manhattan. But when he calls an elephant trainer a monster, the man leaves the animal with Tim to teach a lesson, only to come back later and find Tim feeding the elephant falafel. The trainer takes his elephant back, and the next day, an Eastern European juggler comes to Tim's office and brings him to the circus, explaining that the falafel has sickened the elephant. When Tim arrives at Madison Square Garden, Stu and his new protester girlfriend are demonstrating outside the circus. Stu asks Tim to sneak them inside. Backstage, the elephant trainer is angry because Tim bonded with his animal, and now the beast is depressed. The trainer forces Tim to be mean to the elephant to break their connection. Stu, who's just finished having sex with his date in front of the lion cages, ends up spooking the elephant, which stampedes and injures a group of clowns. The ringmaster comes out to reprimand Tim and explains that the circus's horrific working conditions extend to all its employees - not just the animals.