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After Twenty Years

by O. Henry

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Why did Jimmy have Bob arrested in "After Twenty Years"?

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In "After Twenty Years," Jimmy knows Bob is a notorious criminal but still feels friendship for him after twenty years. This feeling of friendship is why Jimmy couldn't arrest Bob himself.

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Jimmy has to have his old friend arrested because it is Jimmy's sworn duty to enforce the law. It should be noted, however, that O. Henry deliberately softens Jimmy's betrayal by making Bob's offense ambiguous. The reader should not assume that Bob is going to spend years in an Illinois prison. The plain clothes man who arrests him uses these words:

"Chicago thinks you may have dropped over our way and wires us she wants to have a chat with you."

Bob may only be wanted for questioning. And, since he is obviously a smooth talker, he may be able to talk his way out of whatever jam he is in. In fact, Chicago may only wanting to question him about somebody else. Furthermore, the arresting officer does not treat him like a dangerous criminal. He talks to Bob in a polite manner and even hands him the note from...

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Jimmy. There is no mention of a gun or handcuffs. The plain clothes man says:

"Going quietly, are you? That's sensible."

Judging from "Silky" Bob's name, manner, and conversation, he is probably a confidence man and not a dangerous criminal. The arresting officer even makes Chicago seem less forbidding by referring to it as "she." She only wants to have a little "chat" with Bob. 

Chicago may have a hard time arranging that chat. Bob cannot just be shipped off to Illinois. He would either have to be extradited, or else Chicago would have to send a couple of detectives to New York to interview him. Bob evidently has money and can hire a good lawyer. He can fight extradition. Chicago may decide she has enough trouble at home without importing more from New York. 

So O. Henry tells the story in such a way that Jimmy does not seem too cruel to his old friend.

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O’Henry is a master of irony.  The ironic thing about “After Twenty Years” is that two good friends agree to meet each other later, but one is a cop and the other is a criminal.  The cop has to decide if he is going to turn in his friend.

Bob and Jimmy were friends in a former life.  When they were young, they were best chums and Bob said Jimmy was “the finest chap in the world.”   People change, but they are still our friends. 

Jimmy valued being a police officer, but he valued the memory of Bob’s friendship.  He had a difficult choice, so he decided to tell another cop who Jimmy was instead of arresting him himself.  He told Bob why he did it in his note:  

When you struck the match to light your cigar I saw it was the face of the man wanted in Chicago. Somehow I couldn't do it myself, so I went around and got a plain clothes man to do the job.

It was a decent compromise.  Jimmy’s identity was more about being a cop than about being Bob’s friend.  He could not live with himself if he let Bob go. 

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Why couldn't Jimmy arrest Bob himself in "After Twenty Years"?

At the end of the story, Jimmy sends Silky Bob a note that says,

Somehow I couldn't do it myself, so I went around and got a plain clothes man to do the job.

We can surmise, from everything that Bob has said about Jimmy, that Jimmy still feels a strong bond of friendship for Bob, even after twenty years have passed. Bob describes Jimmy as a fine, upstanding person, who unlike Bob, never wanted to leave New York. Bob calls Jimmy the "truest, stanchest old chap in the world." He refers to Jimmy as a "plodder," the kind of person who works slowly and faithfully at one job, rather than flit around to different criminal activities as Bob has done in a quest to get rich quickly.

Ironically, Bob's talk shows he feels he has been more successful than Jimmy. It also shows he has complete faith in this old friend. However, it is the very characteristics in Jimmy that Bob admires—loyalty, faithfulness, and integrity—that would lead him to put his duty to his job first and have his old friend arrested.

Jimmy's note suggests he is a person of heart and feeling. As much as he knows he has to do the right thing and get criminals off the street, he still remembers his old friend with fondness. Having to arrest Bob is upsetting to him.

The story is, on one level, a study in character. An appreciation of the kind of person Jimmy is pulls Bob back to meet with his old friend, but this appreciation is Bob's undoing.

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When Jimmy encounters Bobby after their lives have diverged for 20 years, Jimmy is in perfect position to apprehend his friend for the crimes he had committed over the years. Unfortunately, he is unable to bring himself to do so, because of the close camaraderie they once shared. Their mutual history and deep friendship gives Jimmy pause, and though he knows the man deserves prison, he still sees him as the close friend he once knew and shared so much with.

Instead of letting him go, scot-free, Jimmy leaves and sends another officer to apprehend Bobby and reveal his identity. It hurts Jimmy too much to imprison his own friend, but he knows justice is more important than his feelings. So Jimmy does the right the the only way he is able to in that moment—by sending someone more detached to make the arrest.

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In "After Twenty Years," Bob returns to New York, where he last saw his friend, Jimmy. When the two parted ways, they agreed to meet at a particular location in twenty years to see where life had taken them. As Bob waits for his friend, he encounters a police officer walking the street to ensure the shops are secured. Bob explains his presence to the police officer explaining that he is there waiting for a friend. It becomes obvious that Bob has been successful. Both his scarf pin and his watch contain diamonds. After a brief conversation, the police officer continues along his beat.

Finally, a man arrives in a trench coat and claims to be Jimmy. They greet each other and agree to go somewhere to talk. As they walk, Bob begins to share information about his career. When they come to a well-lit place, Bob discovers that the man in the trench coat is not Jimmy but is instead a police officer. The police officer calls him "Silky" Bob and tells him that he is wanted by the police in Chicago. Before taking Bob to the police station, the police officer hands him a note from Jimmy. Bob then realizes that Jimmy was the police officer he first encountered. In the note, Jimmy explains that he could not arrest Bob himself. While he does not give a reason for this, the reader can imply that Jimmy doesn't arrest Bob, because he values their friendship. However, while the friendship is important to Jimmy, he does not place it above the law. Jimmy sends the man in the trench coat, a plainclothes police officer, to arrest Bob instead.

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