Twenty years earlier, he explains, he and his friend had dinner at a restaurant called "Big Joe" Brady's, which used to be located where the hardware store stands. The officer confirms that this was the site of the restaurant up until five years earlier, when it was torn down. At the time of their last meal together, the man continues, he was eighteen years old and his friend Jimmy was twenty. The two had grown up together and were the closest of friends, but the man was leaving the next morning to go out to the West to find his fortune, and Jimmy was the type of person who would never leave New York. After eating their dinner that night, they agreed that no matter where they were or what they were doing, they would both do all they could to return to that same spot at that exact same time, ten o'clock, exactly twenty years later.

The officer expresses interest, asking why they had been in contact so seldom over the past twenty years. The man briefly explains that he has been busy in the West trying to make his fortune. He checks the time on his watch, which is adorned with diamonds, indicating that he has been successful in his business endeavors. The time is three minutes before ten o'clock, the precise moment that they are scheduled to meet. The officer stays a few minutes more, and it is after ten o'clock when he says goodbye and leaves.

The man waits twenty minutes more. Finally, another man approaches, bundled up against the light rain that has started to fall. The new man calls the man in the doorway Bob and answers to the name of Jimmy Wells. As they chat, Jimmy points out that he has not done as well financially as Bob: he has a position in a city department. He suggests that they go to a place that he knows of nearby, where they can get out of the rain and have a long talk about old times.

When they pass through the light emanating from the window of a drug store that is still open, Bob looks at the man he is with and exclaims with certainty that he is not Jimmy Wells. Though a man can change much in twenty years, he explains, the shape of his nose could never be so drastically altered. The other man says that he is in fact a plainclothes police officer, and that the man, whom he now refers to as "Silky" Bob, has been under arrest since they met ten minutes ago for warrants issued in Chicago.

He gives Bob a note and says that it is from "Patrolman Wells." In the note, the real Jimmy Wells explains that he was in fact the officer who was with Bob at the site of "Big Joe" Brady's restaurant at ten o'clock, but that when Bob struck a match to light his cigar, he recognized Bob's face as the one wanted in Chicago. Jimmy did not have the nerve to arrest his old friend, so he had left before he could be recognized and found a plainclothes officer to arrest him.