Dalrimple Goes Wrong

What happens when virtue doesn’t pay? A man learns how to get ahead—by looking the other way.

Originally published in The Saturday Evening Post on June 5, 1920, Dalyrimple Goes Wrong was part of Fitzgerald’s broader exploration of American ambition in the early Jazz Age. He wrote it shortly after his rapid rise to fame, riding high on the success of This Side of Paradise and reveling in the public’s fascination with flappers, bootleggers, and broken rules.

But this story takes a darker turn. It was written during a period when Fitzgerald began to question the values that underpinned the success he was enjoying—namely, the uneasy alliance between appearance and ethics in American society.

The Story
Bryan Dalyrimple is the golden boy—a war hero, a man of charm and good breeding, someone who should succeed by doing everything right. But the postwar world he returns to doesn’t reward honor; it rewards hustle, networking, and bending the rules.

When a series of low-paying jobs humiliate him, Bryan begins to rethink his moral code. One thing leads to another, and soon he’s entangled in the world of petty crime, gradually justifying each decision with smooth rhetoric and a smile in the mirror. He tells himself he’s still a good man. Maybe even better than most. After all, isn’t he just doing what everyone else is doing… only better?

As Bryan ascends the social ladder through fraud and charm, Fitzgerald offers no easy condemnation—just a disquieting portrait of a man who believes he's earned his success, even when it’s stolen.

This is Gatsby before Gatsby—a cautionary tale of self-invention, disillusionment, and the moral price of ambition.

Published: June 5, 1920 (The Saturday Evening Post)