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But being Frank DePalma won't be easy for Monk, as he learns when DePalma's beautiful girlfriend, Lola, arrives at his hotel room looking for love. It's a stressful situation for Monk, but he manages to keep his cover while avoiding Lola's advances. Monk also learns the first piece of information relevant to his mission: DePalma was hired by mobster Jimmy Barlowe.

Monk meets with Barlowe and a couple of his henchmen. Barlowe gives Monk the name of his target for assassination: an old man named Stanley Greenblatt. Except for the suspicions of one of Barlowe's men, a young hot-head named Lenny, Monk is successful in passing himself off as Frank DePalma.

Monk returns to FBI headquarters with all the information Agent Stone wanted. With Monk's work apparently done, Natalie and Stottlemeyer push to end the undercover operation. But with Monk doing such a great job, Agent Stone wants more. Stanley Greenblatt has no apparent mob connections, and Agent Stone wants Monk to continue and try to learn why Barlowe wants Greenblatt dead.

Monk agrees to go on, but soon finds himself consumed by the "role" of Frank DePalma. When Monk gets physical with a vacationing Harold Krenshaw, Stottlemeyer and Agent Stone pull the plug on the operation. But Monk, filled with bravado from his time as DePalma, refuses to quit. Monk storms off, determined to find out why the mob wants to kill Stanley Greenblatt.

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