Boxer Chuck Nelson (Kenneth Tobey) is the light heavyweight champion of the world. He unexpectedly wants to quit after losing a championship bout and no one including his family knows why. The fighter's manager (Morey Amsterdam) implores his friend O. Henry to help discover the reason why and persuade Nelson to book one last fight that he "can't lose" so he can go out on top.

"The O. Henry Playhouse" is a 1957 single season, 39-episode TV series. O. Henry (William Sydney Porter) is considered one of America's greatest writers of short stories. His writings are laced with humor and irony and often end with a sly twist ending. Veteran character actor Thomas Mitchell stars in each episode as writer O. Henry himself as he relates his stories to his publisher, his housekeeper, a barber, a bartender, or the cop on the beat. In some episodes, O. Henry meets his characters as he discovers firsthand the story he will later write. This unique storytelling method gives great insight into the famous author's creative process.