The Offshore Pirate

A spoiled heiress, a stolen yacht, and the stormy waters between fantasy and truth.

Fitzgerald wrote “The Offshore Pirate” in the spring of 1920, just weeks after marrying Zelda Sayre. He was still riding high on the success of This Side of Paradise, and was feverishly turning out short stories for The Saturday Evening Post, which paid handsomely—and quickly. These magazine pieces became his bread and butter, bankrolling his extravagant new life with Zelda and reinforcing his image as the literary voice of the Jazz Age.

The story was published in The Saturday Evening Post on May 29, 1920, and its playful tone, flirty dialogue, and air of romantic rebellion made it an instant hit with readers. It was one of several that would be gathered into Flappers and Philosophers later that year, helping to cement Fitzgerald’s early fame.

The Story
Meet Ardita Farnam: wealthy, headstrong, and deeply bored with society’s expectations. She lounges on the deck of her uncle’s yacht, dreaming of scandalous adventure and longing for something—anything—that might make her heart race.

Enter Curtis Carlyle, a pirate with a saxophone (yes, really), who commandeers the yacht with his ragtag crew of jazz musicians. Ardita is intrigued. Enchanted, even. As they sail off into rebellion, she discovers a delicious freedom in throwing off propriety—and perhaps, something like love.

But things aren’t what they seem. The pirate’s charm has layers, and so does the story. In true Fitzgerald fashion, the twist reveals more than a clever plot point—it exposes the fragile masks we wear when we want to feel brave, and the lengths we go to in order to rewrite our own narratives.

Published: May 29, 1920 (The Saturday Evening Post)