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The book's story centers on Ernest "Chili" Palmer, a small-time shylock (or loanshark) based in Miami. After a run-in with mobster Ray "Bones" Barboni over a stolen coat, Chili is sent after Leo Devoe, who has scammed an airline out of $300,000 in life insurance by faking his own death. Leo had been aboard a plane whose flight was delayed, prompting him to disembark and go drinking in the airport bar. Leo misses the plane's takeoff, and when it crashes, his "widow" receives a check for $300,000, money which Leo takes to Las Vegas.
After relieving Leo of the money in Vegas, Chili finds a more interesting assignment: the casino is looking to collect from Harry Zimm, a horror film producer based in Los Angeles. Chili, himself very interested in the movie industry, heads for L.A. to make Harry pay.
Chili lets his love of movies overshadow his collection job. He sneaks into the house of actress Karen Flores in the middle of the night, startling both Harry and Karen, who are together in bed. After he warns Harry to pay his Las Vegas markers, he explains that he has an idea for a movie. Harry is immediately taken in by Chili's charm and his movie premise, whereas Karen is still skeptical.
Chili recounts Leo's story to Harry in the third person, as if it were a work of fiction. Karen is on to him, pointing out that the story clearly isn't fictional because she saw the plane crash in the news, realizing Chili is obviously the shylock in Chili's movie idea.
The next morning, Harry asks for Chili's help in dealing with a script he wants to buy. Harry tells him this script, Mr. Lovejoy, could be Academy Award worthy material. "It'll be my Driving Miss Daisy," Harry assures Chili. There are, however, two problems: Harry does not own the script, his writer's widow Doris Saffron does, and she wants $500,000 for it; and he guaranteed a $200,000 investment from Bo Catlett, a local limo driver and drug dealer, to make another movie called Freaks. (Harry gambled Bo's $200,000 away in Vegas in hopes of making the $500,000 he needed for Mr. Lovejoy). In a meeting with Bo and his sidekick Ronnie Wingate, Harry and Chili tell them that, while their investment in Freaks is sound, they are making another movie first. Bo tells them to move the money into this new picture; Harry says he cannot, as the new movie deal is "structured."
Meanwhile, Bo is involved in a Mexican drug deal which doesn't go through. He has left the payment in a locker at the L.A. airport, but the Colombian sent to receive the money, Yayo Portillo (Bo keeps calling him Yahoo), does not feel safe unlocking the locker with so many DEA agents staked out nearby. Bo later meets Yayo back at his home, and after Yayo threatens to tell the DEA who Bo is, Bo shoots him.
Bo soon offers the locker money to Harry as an investment, telling him to send Chili to get the money. Chili senses something wrong, signs out a nearby locker as a test, and sure enough is taken for questioning by drug officials when he tries to open it.
Chili and Karen are meanwhile seeking the interests of Martin Weir, a top-tier 3 time Oscar nominated Hollywood actor to whom Karen was once married, to play the lead in Harry's film.
The loose ends are tied up when Ray comes to Los Angeles looking for the money Chili collected from Leo, only to find the key to the locker from the failed drug deal in one of Chili's pockets. Thinking Chili has stashed his cash in a locker, he goes to the airport and is busted by drug officials. In a final showdown with Bo, Bo s double-crossed by his partner, Bear.
The novel ends with Harry, Chili, and Karen having visited a few production studios and wondering why writing the ending of a story was always the hardest part.