The short story "After Twenty Years” is one of over 113 short stories written by O. Henry, during a three-year period between 1902 and 1905. The New York World, where he worked during that period, only allowed him the space of one page for a story. Therefore, this particular short story, like most of the others, is very short.
The story takes place around 10 p.m. along a dark, windy New York City business avenue, mostly within the darkened doorway of a closed hardware store. This particular location had been a restaurant until five years ago. The weather worsens as the drama builds going from "chilly gusts of wind with a taste of rain” to a "fine, cold drizzle falling, and wind had risen from its uncertain puffs into a steady blow.”.
The plot begins with a policeman "on the beat” who discovers a man standing in the dark doorway. The man then proceeds to explain why he is there. He and his best friend, Jimmy Wells had parted exactly twenty years ago to make their fortunes and had promised to meet at that spot "After Twenty Years”. He had gone west and gotten rich and was sure his friend, Jimmy would meet him if at all possible. They talked a while and the policeman carried on. The man from the west wonders if his friend will show. The drama increases in anticipation of the rendezvous. Twenty minutes later, another man, who we assume is his long lost friend, greets him warmly and they walk arm in arm discussing careers until they come to a will lighted corner. The man from the west gets a good look at his companion and discovers that he is not his friend, Jimmy. We are treated to several surprises at this, the climax of the story: 1) The man from the west is under arrest, 2) He is actually 'Silky Bob', a gangster from Chicago and, 3) The stranger is a plainclothes policeman. However, it seems that three surprises are not enough. We get the "real” surprise ending when the plainclothesman hands Bob a note from Patrolman "Jimmy Wells”, his friend who is actually the policeman from the beginning of the story.