Chili Palmer, a Miami mobster and loan shark, finds himself suddenly working for his arch enemy, Ray "Bones" Barboni, after the heart attack death of Palmer's longtime boss, Momo. Previously, Chili has slugged "Bones" because he had taken Chili's jacket without his permission from a restaurant coat room. Chili and Bones constantly clash, and as his new boss, Bones orders Chili to collect a debt from a Miami drycleaner named Leo Devoe who was reported to have been killed in a plane crash, but Chili learns Devoe has successfully faked his own death after deboarding from the plane before it crashed after take off. With Leo's hat and clothing still on the crashed aircraft, the burned clothing allowed his wife Faye DeVoe to claim $300,000 in a quick insurance airline settlement. Leo has taken all of the settlement money from Faye, and has traveled to Las Vegas. While tracking Leo down there, Chili picks up a second job to collect a 300K gambling debt from a B movie film director named Harry Zimm. In Los Angeles, Chili quickly locates Harry, who is sleeping over at actress Karen Flores' Hollywood home. Chili promptly wakes up and lectures Harry, and scares him into honoring his casino debt, and he also warns him to pay the Mesa Casino the 300k he owes them within 30 days. Seemingly a bit drunk, Harry loudly agrees. Knowing that Harry is a movie director, and having seen his movies, Chili pitches a thinly veiled story of his own recent mob life experiences, including the airline insurance death scam by Leo, as a possible film idea.