Set at the turn of the twentieth century in New York City, O. Henry's narrative begins with a policeman walking his regular beat. Twirling his police stick, he checks the locked doors and doorways. In the doorway of one particular closed business, the policeman comes upon a man who leans with a cigar in his mouth.
- The policeman
Named Jimmy Wells, the beat policeman on the street on which the narrative opens, is a lifelong resident of New York City, who has had a friend from his youth named Bob that invited him to move West where they could seek their fortunes. But, Jimmy, a true city boy who cannot leave his home, declines and the two part ways with the promise that they will meet at their favorite restaurant in twenty years. Having lived all these years in New York, Patrolman Well has established himself as a respected policeman, a man of integrity and decency. In fact, he values his friendship with Bob so much that when he discovers the identity of 'Silky' Bob, an outlaw, matches that of his boyhood friend, he does not have the heart to arrest him. Instead, he sends a detective to meet Bob and apprehend him.
- 'Silky' Bob
Unlike his virtuous friend, Bob travels West and finds oppoturnity, but it is not legal opportunity. For, when he lights his cigar in the doorway of the former "Big Joe Brady's" restaurant, explaining to the patrolman that he waits for his truest friend, Jimmy Wells, with whom he has made a pact to meet these twenty years later, the policeman recognizes him from wanted posters of Chicago. For, the "little white scar near his right eyebrow" and his ostentatious diamonds in his scarfpin and watch match the description of 'Silky Bob.'
When a man approaches Bob in the darkened doorway, he believes the man is his old friend Jimmy Wells. However, when the man steps under a streetlight, Bob has a recognition this time: The man is not his old friend, who did not have the heart to arrest Bob himself.