O. Henry uses Jimmy Valentine's dialogue to characterize him. Among his other traits, Jimmy is a very cautious man. There are several examples of dialogue early in the story which support this statement. When Jimmy is summoned to the warden's office to receive his pardon, the warden tries to give him a lecture.
“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.”
“Me?” said Jimmy, in surprise. “Why, I never cracked a safe in my life.”
Naturally this makes the warden recall that Jimmy has been serving ten months of a four-year sentence for cracking a safe in Springfield.
“Of course not. Let's see, now. How was it you happened to get sent up on that Springfield job?
“Me?” said Jimmy, still blankly virtuous. “Why, warden, I never was in Springfield in my life!”
This dialogue not only serves as characterization, but it provides exposition and also shows that Jimmy is a likeable fellow. The warden likes him and is trying to give him some good advice. Although Jimmy seems impervious to such advice, it may have a delayed effect on him when he falls in love at first sight with Annabel Adams and decides to reform.
After Jimmy is released he goes to the building where he keeps a room on the second floor. Mike Dolan, the owner, runs a cafe on the lower floor, and he seems to cater to the underworld. When Jimmy comes back down with his suitcase full of burglar tools, Mike shows that he knows a lot about Jimmy's line of work.
“Got anything on?” asked Mike Dolan, genially.
“Me?” said Jimmy, in a puzzled tone. “I don't understand. I'm representing the New York Amalgamated Short Snap Biscuit Cracker and Frazzled Wheat Company.”
The meetings with the warden and with Mike Dolan show Jimmy that he is getting too famous as the best safecracker in the business. Mike Dolan must talk about him with his underworld cronies, so Jimmy's exploits must be common knowledge all over the region. This is what prompts the cautious young man to move to Elmore, Arkansas, where Fate decrees that he should fall in love and decide to go straight. Unfortunately, he has also attracted the attention of his old nemesis Ben Price, and the detective traces him to Elmore with the intention of arresting him for the three bank jobs he pulled immediately after being released from prison.
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