Based on the debut novel by Hunter S. Thompson. Tiring of the noise and madness of New York and the crushing conventions of late Eisenhower-era America, Paul Kemp (Johnny Depp) travels to the pristine island of Puerto Rico to write for a local newspaper, run by downtrodden editor Lotterman (Richard Jenkins). Adopting the rum-soaked life of the island, Paul soon becomes obsessed with Chenault (Amber Heard), the wildly attractive Connecticut-born fiancée of Sanderson (Aaron Eckhart). Sanderson is one of a growing number of American entrepreneurs who are determined to convert Puerto Rico into a capitalist paradise in service of the wealthy. When Kemp is recruited by Sanderson to write favorably about his latest unsavory scheme, the journalist is presented with a choice: to use his words for the corrupt businessmen's financial benefit, or use them to take the bastards down.