“The Offshore Pirate” was first published on May 29, 1920, Fitzgerald’s third story in The Saturday Evening Post that month. It would later be included in his first collection of short stories, Flappers and Philosophers (1921). The story begins with a young aristocrat, Ardita, on a yacht anchored close to shore. She is reading The Revolt of the Angels by Anatole de France. She argues with her exasperated uncle who is intent on marrying her off to a young man named Toby.

She is defiant; her rebellion appears to be a combination of general teenage angst, independence, and a sense of entitlement. She claims that her defiance is courage and faith in herself. A feminist interpretation of Ardita as a strong woman may very well be overshadowed by her presentation as an overprivileged aristocrat. The fact that Ardita is reading The Revolt of the Angels and that the yacht is named Narcissus underscores the satire of Ardita and Toby as self-indulgent, high-society types who romanticize rebellion as a lark in stark opposition to real rebellion, which is the attempt to change the society on which these aristocrats thrive.

Left to herself while her uncle goes ashore, Ardita and the crew are overrun by pirates—Curtis Carlyle and his Six Black Buddies. Ardita and Carlyle strike up a friendship that blossoms into love. Carlyle tells her of his upbringing in the only White family in a Tennessee town and his rise to successful musician turned rebel thief. Carlyle describes his unsuccessful attempt to go solo, to avoid spending “the golden years of his life gibbering round a stage with a lot of black men.” It was then that he turned to crime. This was all a lie. In the end, he reveals he is not Carlyle but Toby Moreland, with whom her uncle had been trying to set her up. In the end, everyone wins (except perhaps the six Black Buddies).

Fitzgerald may have been subtly commenting on the White perspective of African Americans in the 1920s by mirroring the portrayal of Babe and five other Buddies as nothing more than props: singers and laborers (in the context of the overall story and in Carlyle’s fabricated narrative). However, Fitzgerald is making a more direct point on the upper class: that aristocrats will be able to justify, to themselves, anything they do to pursue their version of the American Dream. Ardita and Toby are elitists feigning rebellion with nothing to rebel against.

Editor Matthew Brucolli notes that this is the first story that develops “Fitzgerald’s recurring plot idea of a heroine won by her lover’s performance of an extraordinary deed," thus invoking Gatsby. Whereas Gatsby failed, Toby succeeded. But the ending, in which Ardita “kissed him softly in the illustration,” reveals that this is either a story or Ardita’s dream. Critics have said that Fitzgerald was either toying with the idea of "storyness" or just toying with the editor. In any case, the final implication that this story is either a psychological or literary illusion underscores the elusiveness of that American dream for all classes. The overlooked aspect of this story is how that dream is elusive to the point of being inconceivable for someone like Babe or the others of the Six Black Buddies, pawns genuinely struggling and generally dismissed by a culture taunted by romanticized notions of aristocratic leisure.