What is the theme of "After Twenty Years" by O. Henry?

The main theme of “After Twenty Years” by O. Henry is that actions have consequences. "Silky" Bob may have made a lot of money as a successful criminal, but his past is about to catch up with him in the shape of his old friend Jimmy.

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One of the principal themes in O. Henry's short story "After Twenty Years" is the way in which time changes people. Both Bob and Jimmy have long memories and have remained true to their word, turning up at the assigned meeting place twenty years after they made a pact to do so. In this way, neither man has changed. However, Jimmy has altered physically to the point where Bob does not recognize him, even though he was expecting to see him there. It may be that Jimmy's uniform acts as a disguise, and that one of the ways in which Bob has changed over the last twenty years is that he now sees a police officer as a generic threat, rather than as an individual who might be his friend.

Bob describes his old friend Jimmy as stalwart and true, though unimaginative, and himself as a more ambitious character, eager to get on in life. As the second officer remarks at the end of the story, time does not change everything about a man, but it may corrupt a good man, turning him into a bad one. The reader can see that the passage of twenty years has intensified the characteristics of the two men, confirming Jimmy on his straight and narrow path, while the ambitious, morally flexible Bob becomes a crook.

Last Updated by eNotes Editorial on January 27, 2021
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Actions have consequences. And bad actions invariably have bad consequences. That's the very simple lesson learned by the serial criminal "Silky" Bob in O. Henry's “After Twenty Years.” It's safe to say that Bob didn't think that he would learn such a lesson on the very same spot that he last met his good friend Jimmy. He'd gotten away with his crimes for so long that he probably thought he was untouchable.

That would explain why he didn't hesitate to return to New York and make good on his long-standing promise that he would meet his old friend Jimmy in front of a hardware store. At no point did Bob think that he was liable to be arrested, least of all with the assistance of his old pal. He'd been riding high for so long that he got complacent.

Bob's decision to return to the scene of his meeting with Jimmy all those years ago proves to be a very big mistake indeed. Jimmy is now one of New York's finest, a police officer who takes his job very seriously. Although he won't arrest Bob himself, that's the only concession he's prepared to make to their friendship. For Jimmy, too, actions have consequences. His decision to join the police force has led him to this moment, where he will help set up his old buddy for arrest.

Last Updated by eNotes Editorial on January 27, 2021
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I believe it would be safe to say that the theme of O. Henry's story "After Twenty Years" is an old one: Crime Does Not Pay. O. Henry contrasts two different characters who have two different philosophies and two different value systems. Bob is greedy and materialistic. He wants to make a lot of money, buy a lot of things, enjoy a life of luxury, and display his success conspicuously. And he doesn't care how he gets the money as long as he gets it. Jimmy is conventional and conservative. He wants a good steady job that is socially useful. He wants a home and a family. Jimmy is probably a staunch Irish-Catholic who takes his wife and children to church every Sunday.

The two men's different philosophies take them on different paths until they finally meet again after twenty years. Jimmy has a good steady job that is useful to society. He likes his work and he has security. When he retires he will receive a pension for the rest of his life. Bob, on the other hand, has made a lot of money through crooked means. But he has no home, no family, no security. The money hasn't really done him much good. He has spent some of it on a scarf pin with a big diamond and a pocket watch decorated with small diamonds.

It is important to him to have other people look at him, to admire and envy him. But he is always on the run, and it is probably inevitable that he will end up in prison sooner or later. In O. Henry's story Bob discovers that he can't even trust the man he thought was his best friend. Bob has no friends because he never stays in the same place long enough to acquire friends, and also because he is not the kind of man that decent people would want to have as a friend. His flashy lifestyle has made him conspicuous, easy to identify wherever he goes. His career ends up with his being led off to jail. If he has a whole string of crimes charged against him in Chicago and elsewhere in the West, he could be spending a long time in state prisons. Crime really does not pay.

Last Updated by eNotes Editorial on January 27, 2021
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To me, there are a couple of main themes in this short story.

The first one is honesty and responsibility.  Jimmy Wells was Bob's best friend and obviously cared for him a great deal.  But even so, he did not look the other way when he found out that his old friend was a wanted man.

The second one is destiny, or maybe the idea that people go their own ways in life.  Two best friends who cared for each other very much came to be on different sides of the law even though they started out from the same place.

I'd say one of those is the main theme.

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