Who came to meet the waiting man?

The first person who comes to meet the man who is waiting in the doorway of the closed hardware store is Jimmy Wells. Neither the waiting man, "Silky" Bob, nor the reader, realizes that the police officer in regulation uniform is in fact Jimmy Wells because O. Henry very cleverly deceives both. The reader thinks this is a policeman who is approaching Bob because he looks a little bit suspicious standing in a darkened doorway on a nearly deserted block. In fact, Jimmy Wells is there to keep the appointment the two men made twenty years ago. Jimmy doesn't get a chance to introduce himself, as he intended to do, because "Silky" Bob, who is a smooth and profuse talker, doesn't give him a chance to do so.

"It's all right, officer,” he said, reassuringly. “I'm just waiting for a friend. It's an appointment made twenty years ago. Sounds a little funny to you, doesn't it? Well, I'll explain if you'd like to make certain it's all straight. About that long ago there used to be a restaurant where this store stands— ‘Big Joe’ Brady's restaurant.”

This not only explains what Bob is doing there, but it also explains why Bob should be waiting for Jimmy in the darkened doorway of a closed hardware store. Normally two old friends would meet at a restaurant or a saloon. Bob thought he would be meeting Jimmy at the same restaurant where they parted twenty years ago. O. Henry plotted his story in such a way that Bob would be standing in the dark. The street itself is dark. Bob can't see the cop well enough to recognize him, and Jimmy can't see Bob until he lights his cigar.

The man in the doorway struck a match and lit his cigar. The light showed a pale, square-jawed face with keen eyes, and a little white scar near his right eyebrow. His scarf pin was a large diamond, oddly set.

The reader does not realize until the end of the story that Jimmy recognizes Bob as the man wanted by the Chicago police when he lights his cigar. Evidently Bob is standing inside the doorway because he wants to get out of the wind and drizzle to light the cigar and smoke it. There are several things that give Bob away. The telegram the New York police received from Chicago could not transmit any kind of picture or sketch, but it would give a detailed description of "Silky" Bob, including the white scar near his right eyebrow and the "oddly set" diamond scarf pin. The telegram would describe the scarf pin much more precisely, since it is such a good identification mark. For example, the diamond might be surrounded by little rubies. It would be one of a kind.

There is a second person who comes to meet the waiting man. The unidentified uniformed cop says goodnight and leaves Bob standing there.

About twenty minutes he waited, and then a tall man in a long overcoat, with collar turned up to his ears, hurried across from the opposite side of the street. He went directly to the waiting man.

This is the plainclothes detective Jimmy Wells recruited to make the arrest. This man takes advantage of the wet and blustery weather to turn his overcoat collar up to his ears in order to hide much of his face. Both Bob and the reader are led to believe that this is Jimmy Wells, since the man greets Bob by name and seems to know a lot about him.

“It's Bob, sure as fate. I was certain I'd find you here if you were still in existence. Well, well, well!—twenty years is a long time. The old restaurant's gone, Bob; I wish it had lasted, so we could have had another dinner there. How has the West treated you, old man?”

Bob doesn't realize until they have walked up the block arm and arm that the stranger could not be his old friend Jimmy Wells. When they reach the front of a drugstore brightly illuminated with the newly invented electric lights, Bob balks. He realizes too late that he has been tricked. He is told that he is under arrest and given the note from Jimmy Wells. At this point both Bob and the reader realize that the uniformed cop Bob had initially been talking to was in fact his old friend Jimmy Wells.