advises. He decides to "live straight." His motive for reforming is falling in love with Annabel Adams, a very pretty and proper small-town girl in Arkansas. She would be shocked, horrified, and repelled by Jimmy if she knew about his past, including the fact that he had served time in more than one prison. Jimmy makes a decision to become worthy of this angelic woman by going straight. It may be that the warden's advice somehow lingered in his unconsciousness and found its way into his consciousness at this critical time. Jimmy remembers especially: "You're not a bad fellow at heart. Stop cracking safes and live straight." Maybe he isn't such a bad fellow at heart. Maybe he really could live straight! He writes a letter to a friend in which he tells him:

Say, Billy, I've quit the old business—a year ago. I've got a nice store. I'm making an honest living, and I'm going to marry the finest girl on earth two weeks from now. It's the only life, Billy—the straight one. I wouldn't touch a dollar of another man's money now for a million.

For a few bad moments at the end of the story, Jimmy's reformation seems in serious jeopardy. But everything works out all right in the end, proving that the warden's advice was not only sound but prophetic.

O. Henry, who always wrote under a pseudonym to hide his identity, spent several years in an Ohio penitentiary. He may have had a similar interview with the Ohio warden when he was released. O. Henry is being utterly sincere when he writes that the only life is the straight one. It may not be as lucrative and flashy as a life of crime, but it has all kinds of amenities that make it much more valuable. O. Henry contrasted the straight life and the crooked life in another of his best stories, "After Twenty Years."

Jimmy is young and cocky. He has a winning personality. Everybody likes him. The warden takes a special interest in him because he sees that Jimmy is a cut above the hardened cons he has to deal with every day. Jimmy seems to be ignoring the warden's well-meant advice, but some of it must be making an impression on him. No doubt Jimmy appreciates the fact that the warden likes him and is trying to save him from the downhill path of a life of crime. Jimmy is acting cheerful and confident, but he has been sobered by the fact that his stay in the prison lasted much longer than he expected. He is beginning to realize that his expertise as a safecracker is a handicap as well as an asset. It is becoming easier to get arrested and harder to get out. He may have important connections on the outside, but these people can forget about him very quickly if he becomes so notorious that he is no longer a good person to know. It is appropriate that the story opens inside a prison. It illustrates the fact that Jimmy is not as smart as he thinks he is. The best thing the warden tells him is the following:

“Now, Valentine,” said the warden, “you'll go out in the morning. Brace up, and make a man of yourself. You're not a bad fellow at heart. Stop cracking safes, and live straight.”

A man who has the intelligence, personality, and talent to be a successful criminal can use the same intelligence, personality, and talent to become even more successful as an honest citizen. When Jimmy decides that he is getting too notorious in the Indiana area and moves to Arkansas, his falling in love with Annabel Adams is not exactly a cause of his decision to reform but more of a catalyst. He has been changing gradually without even realizing it. He has been more or less unconsciously to the realization of the truth he expresses in a letter to his old friend.

Say, Billy, I've quit the old business—a year ago. I've got a nice store. I'm making an honest living, and I'm going to marry the finest girl on earth two weeks from now. It's the only life, Billy—the straight one. I wouldn't touch a dollar of another man's money now for a million. 

Jimmy is still in danger of having his past catch up with him. His nemesis Ben Price is on his trail because of the four bank jobs Jimmy pulled off in Indiana right after his interview with the warden. But Ben Price decides to give him a break after witnessing how he sacrifices his whole future in order to rescue a little girl who has accidentally become locked in Annabel's father's bank vault.

Jimmy's attitude towards the warden is dismissive. He playfully mocks the warden by displaying nonchalance and faux innocence when the warden gives him some unsolicited advice.

According to the story, Jimmy has only served 'ten months of a four year sentence.' Because Jimmy has influential friends, his stints in prison always appear to be short. In Jimmy's eyes, he can afford to disregard the warden's impassioned advice. For his part, the warden thinks that Jimmy is a good man who just needs to buckle down and to 'live straight.'

In the conversation with the warden, Jimmy never takes the bait. He refuses to engage the warden in a discussion of his future. Each time the warden questions him about his motives or his part in a previous heist, Jimmy resorts to humor to distract the warden. In the end, the warden can only dismiss Jimmy with a blunt 'Better think over my advice, Valentine.' When Jimmy is released the next day, the warden shakes Jimmy's hand and hands him a cigar. With Jimmy's confident stance, we know that we haven't heard the last of this enigmatic character.