The tone of “A Retrieved Reformation” is simultaneously ironic and earnest. O. Henry opens the story poking fun at the corruption and ineffectiveness of the criminal justice system, as seen in the following passage:
At a quarter past seven on the next morning Jimmy stood in the warden’s outer office. He had on a suit of the villainously fitting, ready-made clothes and a pair of the stiff, squeaky shoes that the state furnishes to its discharged compulsory guests. The clerk handed him a railroad ticket and the five-dollar bill with which the law expected him to rehabilitate himself into good citizenship and prosperity.
O. Henry’s tone in this passage is sarcastic and mocking. This comes across in the description of Jimmy’s “villainously fitting” clothes and “the stiff, squeaky shoes that the state furnishes to its discharged compulsory guests.” As someone who spent time in prison, O. Henry is likely pulling from personal experience in his disparaging comments about prison garb. His comment about how a single train ticket and five-dollar bill is all the state gives prisoners to help them “rehabilitate [themselves] into good citizenship and prosperity” again comes off as bitter and mocking. Clearly, O. Henry does not consider this a suitable investment, implying that it’s likely ex-prisoners will resort to criminal activity to survive (and therefore likely end up back in prison).
The tone shifts into a much more earnest register when Jimmy travels to Elmore and sees Annabel for the first time, falling in love with her on the spot. After this moment, Jimmy finally has the proper motivation to redeem himself, working hard to earn money as a shoemaker while courting Annabel. As Jimmy loses his bitter and jaded orientation to the world, the narrator loses this bitter edge as well.
