Do you think the warden feels that Jimmy is virtuous?

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In answer to your question, I don't think that the warden believes that Jimmy is virtuous at the beginning of the story, but he does believe that Jimmy has the capacity to become virtuous. At this point, Jimmy is still a career criminal, and the warden is certainly aware of...

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In answer to your question, I don't think that the warden believes that Jimmy is virtuous at the beginning of the story, but he does believe that Jimmy has the capacity to become virtuous. At this point, Jimmy is still a career criminal, and the warden is certainly aware of this (consider Jimmy's response to the warden—in which he denies any criminal wrongdoing—and the warden's response to this denial). Hence the advice he gives Jimmy at the start of the story: he advises Jimmy to give up his life of crime and to make something of his life.

O. Henry's story proceeds to follow Jimmy as he makes an honest life for himself and then, in the story's conclusion, actively uses his criminal skills in the service of something good (the rescue of a child trapped in a safe).

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The chief prison officer or warden if you like, does not think that Jimmy is virtuous. However, he feels that Jimmy “is not a bad man at heart”. A virtuous person is one with high moral standards. Jimmy does not have high moral standards because he is a master safecracker and has even been imprisoned for this. However, the chief prison officer feels that Jimmy is a good man, who is making the wrong kind of choices in life. Perhaps, he cracks safes because he has no other means of income. This is why the warden advises him to make good use of his time out of prison to make a man of himself, to change his criminal ways. Note that Jimmy responds to the warden’s advice by insisting that he has never cracked a safe in the whole of his life. He feigns complete ignorance of the wrongs he has committed in his life. In spite of this denial, the warden still tells him to think about the advice he has given him.

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