How are "Silky" Bob and Jimmy Wells described in "After Twenty Years"?

"Silky" Bob is described as a pale man who has "square-jawed face with keen eyes." His most notable features are a white scar by his eyebrow and the diamond scarf pin he wears, which is large and "oddly set." He smokes a cigar. He comes across as well-to-do and flamboyant because of his cigar and diamond (and perhaps a bit déclassé to be flaunting his wealth with a large jewel).

We don't get much precise physical description of Jimmy Wells as that would ruin the "twist" of the story, but we see him walking up and down his beat, twirling his baton. He is alert with a "watchful eye" and obviously does a good job policing—as his area is peaceful. We are told that he is "a fine picture of a guardian of the peace." At the end of the story, we learn he has a pug nose.

The description of each character fits the different directions they have gone in life: Bob displays the all the signs of a risk-taking, flamboyant criminal while Jimmy shows the steadiness and ordinary appearance of a man faithfully doing his job.

O. Henry's description of Bob's face by the light of his match has a double purpose. First, it is necessary to enable Jimmy to recognize Bob as the man who is wanted by the Chicago police. Second, it gives the author an opportunity to tell the reader what Bob looks like. We must remember that both these men have changed a lot over the past twenty years. They are not a couple of kids talking to each other, but men who are both approaching middle age and who have acquired great stores of "street smarts" in their respective vocations. They are two mature men standing in the same spot where they said goodbye as mere boys twenty years before. The "white scar" near Bob's right eyebrow serves a dual purpose as well. It helps Jimmy to identify him as the wanted man, and it suggests that Bob is a tough customer who has been in fights during his years in the West.

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. The reader will not discover until the end of the story that the policeman is in fact Jimmy Wells, but the reader will have formed a strong impression of Jimmy by that time and will understand why he found it impossible to let his old friend Bob escape from the long arm of the law. We do not know exactly how long Jimmy has been a cop, but it could have been almost twenty years. He was twenty years old when he and Bob said goodbye in "Big Joe" Brady's restaurant. That would be about the age when he would be thinking about finding good steady employment. O. Henry's description of the policeman in the opening paragraphs suggests a man who has had many years of police work and is thoroughly set in his ways as well as content in his role and duties as a uniformed cop.

What similarities exist between Silky Bob and Jimmy Wells in "After Twenty Years"?

Silky Bob and Jimmy Wells are both good friends and keep promises.

It is pretty remarkable that both Silky Bob and Jimmy Wells showed up to keep a date made twenty years before.  They either are good friends, or men of their word.  We know that Jimmy Wells is a man of honor.  Being a cop is important to him.

The policeman on the beat moved up the avenue impressively. The impressiveness was habitual and not for show, for spectators were few. The time was barely 10 o'clock at night, but chilly gusts of wind with a taste of rain in them had well nigh depeopled the streets.

In other words, Jimmy Wells is a cop through and through.  Bob says he is trustworthy.  This is why he turns in his friend, even though the friend in him does not want to.  He is also an honorable man, which is why he gets another cop to do it.  He can’t bring himself to do it.

Jimmy is also sure that he can depend on Bob.

"Bless my heart!" exclaimed the new arrival, grasping both the other's hands with his own. "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.

Of course, Bob has turned out to be a criminal.  Nobody’s perfect.  Still, he kept his word.  He came when he agreed to.  Bob may be Silky Bob from Chicago, Wanted Man, but he is also the same reliable Bob who made a promise twenty years ago and kept it.  This is another reason Jimmy does not want to turn him in.  He is aware that Bob showed up only because he was keeping a promise.  The Bob who showed up was the old Bob, the Bob from twenty years ago.

Provide a brief characterization of "Silky Bob" and Jimmy Wells from "After Twenty Years".

In writing your essay, start with an introduction to the story you are discussing and briefly explain the characters.  You might want to explain their relationship to one another and why they are meeting on this particular night.

The second paragraph should be about one character, Jimmy Wells, and his qualities. It should give examples of why you have given the character these qualities --- specific things from the story.

The third paragraph should be about the other character, Silky Bob, and his qualities. It should give examples of why you have given the character these qualities - specific things from the story.

Your last paragraph can be an opinon. Which opinion you choose can be up to you.  Do you think that Jimmy was right to have his friend arrested?  Do you think that one character is better developed than the other?  Do you think that one character is a better person than another?  You choose the opinon you want to have, but choose ONLY ONE and develop it.  An opinion is NO good without a reason.  So you must have a reason for your opinion.  State your opinion and then tell your reason WHY you think that way.   You should have at least two reasons why you have your opinion.  If you do not have at least two reasons, you do not have enough information to make your opinion valid.

That should give you four well-developed paragraphs if you write them correctly and include all the details.  

Jimmy Wells 

1.  self assured.  He walks his beat "Impressively".  O'Henry tells us that this impressiveness was "habitual" and not for show.  He is not trying to impress anyone. He made a "fine picture of the guardian of the peace"

2. Observant: He casts his "watchful eye" down the street. He recognizes his friend's face as the man "wanted in Chicago".

3. Plodder: He wasn't the hustler that Bob was.  That is why he stayed in New York.  Bob says that a man gets "in a groove in New York."

3. Honest: His friend was a wanted criminal.  Jimmy couldn't ignore that and had to arrest him but couldn't do it himself. He does tell Bob in a note that he was the reason Bob was arrested. 

4. A friend: Bob describes him as the "truest, staunchest old chap in the world."  Again, he couldn't arrest his friend and says "Somehow I couldn't do it myself" .

5. Punctual: He was there at the appointed time, and Bob knew he would be there.  

Silky Bob

1. Adventurer: He was the one who set out for the West looking for his fortune. He says that "It takes the West to put a razor-edge on him" (a person).

2. Hustler: He says that he "kept hustling it over pretty lively"

3. Punctual:  He is there on time

4. Successful:  He wears a big diamond on his scarf. The police officer asks him if he was successful in the West.  He says, "You bet. I hope Jimmy has done half as well."

5. Criminal: He is a wanted man in Chicago. He seems to have gotten into some trouble because he has a scar over one eye.

6. Arrogant: Leans against the store and lights his cigar, and pulls out an impressive watch.  He says that he had to deal with "some of the sharpest wits to get my pile"

7. Treasures his friendship:  He travels over a thousand miles to meet his friend and "it's worth it if my old partner shows up"

8. Patient: The police officer asks him if he is going to call time on his friend at 10 sharp, and Bob says "I should say not!... I'll give him half an hour at least.