This nickname suggests a lot about why Bob is wanted by the Chicago police. He acquired that nickname by being a smooth talker and a smooth operator. Although the reader is never given any specifics about Bob's activities in the West, it seems apparent that Bob was operating as a confidence man.

This shows that Bob hasn't the slightest suspicion that he has been talking to his old friend. He calls the policeman "officer." It also shows that Bob does not realize he has given away important information: that he will be standing there for a half-hour.

O. Henry had to explain why Jimmy arrived on time for the ten-o'clock appointment but would still have enough time to arrange to get Bob arrested. O. Henry does not want the reader to suspect that the cop might be Jimmy Wells. The reader thinks that the cop stops to talk to Bob because Bob looks suspicious standing inside a darkened doorway. Bob is only doing that because that is the appointed spot for the reunion, even though the restaurant was torn down five years ago. Bob can't wait anywhere else. He has nothing else to do because, after twenty years of absence, he is a stranger in town. Besides, he wants to light his cigar, and he has to remain in the doorway to smoke it because the weather outside the doorway is too wet.

The plainclothes officer has been primed with information by Jimmy. He has been told that Jimmy was twenty years old when he last saw Bob at "Big Joe" Brady's restaurant.

Jimmy has to get back to the precinct house to find another officer to make the arrest. However, he can't seem to be in too much of a hurry, so he continues trying doors until he passes out of sight. This fools Bob and also fools the reader, who must believe this was just a beat cop who only stopped to check out a man who appeared to be loitering.

The policeman's identity is still unknown to the reader. Jimmy has decided to have Bob arrested by another officer. He needs to make sure that Bob will remain in the doorway for some little time. Jimmy has to get back to the precinct station, find someone else to make the arrest, and give that other officer time to get back to the doorway. The fact that Bob, whose identity is still unknown to the reader, has just lighted a cigar will help to keep him in the doorway because he can't smoke his cigar in the rain.

The plainclothesman is effectively placing Bob under arrest, preventing him from getting away if he should realize that this man is not his friend Jimmy Wells. When they walk off together, they will be walking "arm in arm," meaning that the plainclothesman still has Bob effectively in custody.

Since other pedestrians have their coat collars turned high, it will not look unusual for the plainclothes detective to be doing the same thing when he arrives twenty minutes later.

Bob, who has not yet been identified to the reader, is content to stand in the doorway and wait because it takes a long time to smoke a cigar and he can't smoke it in the rain.

This is the kind of praise that makes it too hard for Jimmy Wells to arrest his old friend Bob personally and gives him the idea of having another officer make the arrest for him.

The policeman is given a cue to ask this leading question because the other man is showing off with his expensive watch and inviting such a question.

Since the policeman is in fact the other man's friend, he ought to know the answer to his question. It may have been that Jimmy Wells tried writing letters to his friend in the West for a few years but never got an answer. The author establishes that "Silky" Bob would have no way of knowing that Jimmy Wells had joined the New York police force. Otherwise, Bob might surmise that the policeman he was talking to was his old friend and not a beat cop checking him out.

This description of the cold and wet weather will serve at least two purposes. It will explain why "Silky" Bob is standing deep inside the doorway-entrance, and it will explain why the plainclothes detective who ultimately arrests Bob will be able to conceal part of his face by wearing an overcoat with the collar turned up.

The author emphasizes that the plainclothes man is bigger than Bob. This makes it less likely that Bob could make an escape. O. Henry does something similar in "A Retrieved Reformation." He emphasizes that the detective Ben Price is a "big man." This insure that Jimmy Valentine would have a hard time trying to escape being arrested.

Bob is unwittingly giving the arresting officer, who has not yet revealed his identify, information that can be used against him by the Chicago police.

Some readers may feel that Jimmy Wells did the wrong thing in betraying his old friend, who had come a thousand miles to meet him after twenty years and who spoke so highly of him. O. Henry seems to be. not excusing, but ameliorating Jimmy's double-cross by showing the actual arrest as rather cordial and not involving physical force, resistance, guns, or handcuffs. The plainclothes detective's statement that "Chicago wants to have a chat with you," suggests that "Silky" Bob may not be in for too much trouble. The Chicago police-- whom the arresting detective refers to as "she," which makes them seem less brutal--only want a "chat." What this apparently means is that they may only want to ask Bob a lot of questions but are not prepared to book him on any specific charges. Bob does not seem like a tough guy but more like a smooth con man. It might be impossible for the Chicago authorities to build a case against him.

This is part of O. Henry's way of characterizing Jimmy Wells. It is important to the story because there is a sharp contrast between these two men. Jimmy is conservative, conventional, and values security. Bob is a gambler at heart. His philosophy is "Nothing ventured, nothing gained." Bob is the kind of man who is likely to go off to the so-called West, actually the Midwest, without any idea of how he was going to survive. Jimmy is the kind of man who would never consider doing such a wild thing.

Bob's nickname "Silky" Bob suggests that he is a confidence man who depends on his wits and smooth talk but is not a violent criminal. This explains why the plainclothes detective does not use any physical force in arresting him or try to put handcuffs on him. It also explains why Bob puts up no resistance, and it further explains why only one man was sent to make the arrest. Bob will try to talk his way out of whatever kind of jam he is in.

It used to be common for two male friends to walk arm in arm. Here is a pertinent quote from Edgar Allan Poe's story "The Murders in the Rue Morgue":

Then we sallied forth into the streets, arm in arm, seeking, amid the wild lights and shadows of the populous city, that infinity of mental excitement which quiet observation can afford.

O. Henry adds this descriptive touch to show that Jimmy is happy in his job. One of the ideas illustrated by this story is that an honest and industrious man is happier than a crooked and predatory man. Jimmy has nothing to worry about, but "Silky" Bob is always on the lam, always looking over his shoulder, and the law finally catches up with him on the night of this story.

Two old themes are apparent in "After Twenty Years." They are:

Honesty is the best policy.

Crime does not pay. 

Bob naturally does not want to tell a cop much about his personal life and his activities in the West. It probably would have been impossible for Jimmy to correspond with him because Bob had to keep moving and had no wish to leave any forwarding addresses behind him. There were no telephones in those days, so it would have been impossible for Bob to call Jimmy for a little chit-chat. Everything about Bob, including his flashy clothes and his gift of gab, suggests that he is some kind of a swindler, a common enough type in the early Midwest. Such a man would have to keep moving on before his victims found out that they had bought stock in nonexistent enterprises or had lost their money in whatever else the scam happened to be. In O. Henry's amusing story "The Man Higher Up," three crooks who are all on the lam happen to get together in a small Midwest town. In spite of all their cunning, all of them are flat broke and in hiding.

There may be a question in the reader's mind as to whether Jimmy Wells intended to keep his appointment with Bob or whether Jimmy even remembered they had an appointment. From the way the story opens, it seems as if the policeman is only on the scene because that is part of his regular beat. Naturally, the reader is led to believe that the policeman only stops to talk to Bob because Bob looks a little bit suspicious standing in a darkened doorway. O. Henry describes the weather as having "chilly gusts of wind with a touch of rain in them." This explains why Bob is standing inside the doorway rather than out on the sidewalk in plain sight. Bob has not even lighted his cigar, which could suggest to a police officer that the man in the doorway doesn't want anyone to see he is there. Bob soon lights his cigar, having realized that he might have looked suspicious. He is doing his best to impress this policeman with his total innocence and poise. He has had plenty of dealings with policemen in the past. He speaks to this one "reassuringly"--perhaps too reassuringly, too glibly. He offers a detailed explanation for his presence without being asked. He immediately lights his cigar and thereby intentionally shows his face. He also intentionally displays an expensive pocket-watch decorated with little diamonds as a way to show that he is a solid, respectable citizen.

It isn't until the very end of the story that the reader is informed that the policeman who first talked to Bob was in fact Jimmy Wells and that Jimmy remembered their appointment and fully intended to keep it. He was only strolling along trying doors because this just happened to be part of his beat and he knew that it was not quite ten o'clock yet.

It is not a strange coincidence that Jimmy should happen to be on patrol at the exact spot and the exact time when he planned to meet Bob. As a beat cop, Jimmy could go anywhere he wanted within his jurisdiction. He must have planned to patrol that particular block at that time because he expected to meet Bob at the former site of "Big Joe" Brady's restaurant.

I believe the moral of O. Henry's "After Twenty Years" is that people change and grow apart. O. Henry's story seems intended to illustrate the effects on people of the passage of time. Unfortunately, everything changes, just as the restaurant where the two friends said goodbye has evolved into a hardware store.

This shows that Jimmy fully intended to keep his appointment with Bob and was not just patrolling his beat. It was just a coincidence that the meeting place happened to be inside that beat. Bob may feel distressed at being betrayed by his old friend, but at least he should feel pleased that his friend didn't fail to keep their appointment.

These words are cryptic. O. Henry may be suggesting that Bob acquired that diamond in some crooked way and had it set by someone other than the jeweler who originially sold it to the lawful owner. Bob might have stolen the diamond or bought it from someone else who had stolen it. Anyhow, there is a good chance that he did not just go into a jewelry store and buy it.

O. Henry's description of Jimmy's manner of patrolling his beat is largely intended to show that he has been a cop for a long time. This fact has had an indelible effect on him. He has become a cop through and through, a man who is dedicated to upholding the law.

Cigar stores were common in big cities. Many of them, for some reason, had a huge statue of an Indian standing in front wearing a full feathered war bonnet. There was usually a lighted gas jet continually burning inside near the counter where men could stop and light or relight their cigars. Cigar stores also sold the daily newspapers. There were no coin machines dispensing newspapers in O. Henry's day. People would buy their papers in cigar stores, hotel lobbies, news stands which also sold magazines, or from men or boys peddling newspapers on the sidewalks.

In O. Henry's time, city streets were patrolled by uniformed cops on foot. They got to know everybody on their beats and kept order effectively. But when criminals began using automobiles in their criminal activities it was necessary for the police to start using patrol cars, and the beat cops gradually disappeared from most of America. In some districts the cops patrolled their beats on horseback. Life was slower-paced. People did not customarily travel very far from their homes. Big cities like New York were made up of separate little districts, which were like towns or villages within the larger metropolis.

O. Henry has the policeman trying all the shop doors to indicate that this is his regular beat.

This shows that the two young men were very good friends. Bob is strongly motivated to go west and Jimmy can't be persuaded to go with them. They compromise by pledging themselves to meet again at the same place in exactly twenty years. 

O. Henry probably inserted this sentence to explain why Jimmy didn't go west with Bob in spite of the fact that they were such good friends. Bob would surely have invited Jimmy to go with him but must have gotten turned down.

The plainclothesman has never seen Bob, and Bob is now standing in a darkened doorway. The arresting officer has to make sure of Bob's identity, and he has to do so without arousing suspicion because Bob could give him an entirely different name.

This line is significant. It softens the blow. The reader doesn't know how to feel about learning that Bob's old friend Jimmy betrayed him so flagrantly. But at least it appears that Bob is not wanted for a truly serious crime such as robbery or murder. He is obviously not that kind of criminal. He is suave and shrewd, most likely a confidence trickster. The arresting officer does not even say that Chicago wants to charge him with any crime. Apparently there is no arrest warrant. Chicago only "wants to have a chat" with Bob. This tends to make Jimmy's betrayal seem less blameworthy. Bob may not have to go to prison at all. He may be subjected to a heavy police grilling when he gets to Chicago, but he is a smooth talker and may talk his way out of whatever trouble he is in. No doubt he has been in trouble many times before.

It is certainly understandable that Bob would wait an extra half-hour for Jimmy to arrive, since Bob has traveled all the way from Chicago to meet him, and also since Bob doesn't know another soul in New York after twenty years.

What Easterners called "the West" in O. Henry's time was what is now called "the Midwest." They probably would have referred to what is now called "the West" as "the Far West" or even "the Wild West."