It should be noted that Jimmy Wells does not know that his old friend is nicknamed 'Silky' Bob. O. Henry does not want Jimmy to know the last name of the man wanted by the Chicago police. Bob's last name is never mentioned in the story. Evidently the Chicago police do not even know Bob's last name themselves but only know him as 'Silky' Bob. If Jimmy had seen Bob's last name included in the wire from Chicago, that would have changed the whole story. Jimmy goes to meet Bob without any idea that Bob is the man wanted in Chicago. There would have been no picture of Bob in the wire because there were no facilities for sending photos or even sketches by wire in 1908. That wire does contain a general description of Bob, plus two specific identifying features. Jimmy recognizes these features when Bob 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 wire from Chicago, in addition to describing the little white scar near the right eyebrow, would have contained a detailed description of the diamond scarf pin. O. Henry only states at that point in the story that the pin is "oddly set," but that is to avoid calling too much attention to it and arousing the reader's suspicion that it must have some important significance. The wire would have specified exactly how the scarf pin was set and what made it so different from all other scarf pins. For example, it might state that the diamond was surrounding by little rubies and set on a gold base resembling a four-leaf clover--or whatever. The diamond scarf pin, more than the little white scar, would be an unmistakable indication that the man in the doorway was 'Silky' Bob.
Bob was called 'Silky' Bob by the police because that was the only name they knew him by. Bob was called 'Silky' Bob by O. Henry because he wanted to avoid giving him a last name. If the wire from Chicago had contained Bob's real last name, then Jimmy would know in advance that his old friend was the wanted criminal. How would this have affected O. Henry's story? For one thing, Jimmy couldn't have kept the appointment and listened to Bob at length without revealing his own identity. It was important to O. Henry's plot, not only that Jimmy should not know that Bob was the wanted man, but also that Bob should not know that he was talking to a cop. Jimmy would have known when he read the wire exactly where the wanted man would be at ten o'clock. He would most likely have given that information to his superior, who would have had Bob arrested without Jimmy ever becoming involved. But that was not the way O. Henry wanted to tell his...
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story. The way he tells it is far more dramatic and emotionally effective.
O. Henry probably had a number of reasons for giving Bob the nickname of "Silky Bob." One was to characterize him as a man who liked luxurious personal possessions, which might include silk shirts, silk neckties, silk handkerchiefs, silk scarves, and silk underwear. Another was to characterize him as a smooth talker and a slick operator. No doubt he was a criminal, but the nickname suggests that he was not a violent one. He had not committed robberies, burglaries, or murders in the West but had probably made his money as a confidence man. His love for luxury goods would also suggest why he had become a crook in the first place.The fact that he was nonviolent would further suggest why he had managed to stay out of the arms of the law up to this night and also why the arresting officer treated him so courteously. The reader feels a bit sorry for Bob, since he trusted his old friend Jimmy Wells who betrayed him. O. Henry wants his surprise ending to stir the reader's emotions in a certain way. He doesn't want the reader to think too badly of Jimmy or to feel too sorry for Bob. Therefore O. Henry mitigates the problem that Bob is facing by suggesting that (1) he is a smooth talker and may be able to talk his way out of the situation he is facing in Chicago; (2) he cannot be wanted for a crime involving capital punishment or a life sentence because he is not a violent criminal; (3) Jimmy's betrayal was not of extremely serious importance, since Bob will probably get off with a grilling or at worst a light sentence. All of these possibilities are suggested by Bob's nickname. The reader would undoubtedly feel differently about Bob's arrest if he were, let us say, wanted for murder and was facing execution. But the plain clothes detective who arrests him tells him that Chicago wants to have a "little chat" with him. The officer does not use handcuffs or pull out his gun. Bob must only be wanted for questioning. There is apparently no warrant for his arrest on any specific charge. This makes his situation look less dire and Jimmy's betrayal less reprehensible.
He was probably given the name "Silky Bob" because silk is a smooth, slick material--attributes that this man had--he was a mobster, a criminal of some sort. His nickname implies that he was smooth and slick and never got caught. He was too crafty for the police--that is until his best friend, now a police officer, caught up with him 20 years later!
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Why is Bob's nickname "Silky" Bob in "After Twenty Years" by O. Henry?
Even Bob's first name is not mentioned until near the end of the story, and the nickname "Silky" Bob is mentioned only once. This is when the plainclothes detective tells him,
You've been under arrest for ten minutes, ‘Silky’ Bob.
Bob's last name is never mentioned in the story. O. Henry has some reason for not wanting to identify Bob by his name. This is undoubtedly because Bob is continually on the lam and probably uses many different names. Jimmy Wells, of course, would know Bob's last name, but he cannot call him by his first name, last name, or nickname when he is talking to him in front of the hardware store because he has quickly decided not to reveal who he is or that he knows who Bob is. Jimmy makes this decision when Bob lights his cigar and Jimmy sees that his old friend is the man who is wanted by the Chicago police. From that point on, there is no exchange of names. Bob speaks of Jimmy Wells, but he does not know he is talking to Jimmy Wells. Bob is called "the man" and "the other," and at one point he is called "the man from the West," but he is not called Bob until the arresting officer arrives on the scene and calls out:
“Is that you, Bob?” he asked, doubtfully.
The plainclothes detective only knows the name because Jimmy Wells has told it to him. O. Henry could not have had Jimmy addressing Bob by name because Jimmy was pretending he didn't know him. Bob would have had no reason to introduce himself by name to a strange cop unless asked to show some form of identification. Both Jimmy Wells and Bob's identities are unknown to the reader until near the end of the story, which is O. Henry's intention because he wants a surprise ending.
Bob probably got the nickname 'Silky' Bob for two reasons. One is because he is apparently a smooth talker, as he demonstrates when he encounters the cop while he is standing in the hardware-store doorway. Bob is slick. He is like silk. Another reason is that Bob has a taste for luxuries, as demonstrated by the diamond scarf-pin he is wearing and his diamond- studded pocket watch. He probably also favors silk clothing. This would easily get him the nickname 'Silky' Bob in underworld circles. Crooks generally go only by their first names or a nickname to avoid being caught.
The word 'Silky' appears only once. The plainclothes detective has to show that he knows the man he is arresting. He has to make a positive I.D. This is why O. Henry has him say,
You've been under arrest for ten minutes, "Silky" Bob.
It may be that the Chicago police do not even know Bob's last name but have identified Bob in their telegram as "Silky" Bob. This would be sufficient for the New York detective to arrest Bob, although Jimmy Wells could supply Bob's last name when booking him. Bob might have many reasons for wanting his last name to be unknown, and Jimmy could cause him a lot of trouble all over the Midwest when he reveals what it is. If Bob is wanted by the Chicago police, he may very well be wanted by the police in a lot of other towns.