O. Henry was a popular writer. He wrote for the masses of mostly urban dwellers who read newspapers. This may explain why his stories are often sentimental and even romantic. Some good examples are "The Last Leaf" and "The Gift of the Magi." A lot of readers could identify with O. Henry's characters because they were facing similar problems, many of which have to do with money. "The Gift of the Magi" is an example of a sentimental and romantic O. Henry story which is all about the shortage of money and the privations so many of his readers had to endure. We can almost visualize O. Henry's readers while we are reading his old stories. They wanted to be assured that there is hope, that good deeds are rewarded, that honesty is the best policy. In "A Retrieved Reformation" they would be hoping that Jimmy's reformation would be successful because love inspired him to be an honest man and live a clean, industrious, conventional married life. Most of O. Henry's readers would thoroughly approve of what Jimmy Valentine writes to an 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....I tell you, Billy, she's an angel. She believes in me; and I wouldn't do another crooked thing for the whole world.
No doubt most of O. Henry's readers would be inclined to overlook the fact that Jimmy had committed three safecracking jobs after being released from prison. Little people in those days did not have much sympathy for banks or insurance companies or big detective agencies like the Pinkertons. They wouldn't think it was necessary for Jimmy to have to pay for his recent crimes, and they would not want to see Jimmy's nemesis Ben Price succeed in tracking Jimmy down and putting him in prison, destroying his hopes of happiness and a respectable small-town life.
O. Henry's readers would have felt pretty much the same way about "A Retrieved Reformation" when it was first published as readers feel about the story today, except that the average contemporary reader would be better educated and more sophisticated. He or she would realize that this was romanticism and not reality. An O. Henry story that comes closer to depicting reality is "After Twenty Years." The central character, "Silky" Bob, does not reform and the policeman, Jimmy Wells, does not allow him to escape but turns him in to the Chicago police in spite of their old friendship. (It would be interesting to imagine how "After Twenty Years" might have had a different ending if, instead of bragging about his illegal exploits, "Silky" Bob had told the policeman that he repented and wanted to reform, change his identity, and lead a straight life.) Another O. Henry story that comes closer than "A Retrieved Reformation" to depicting harsh reality is "The Furnished Room," in which two lovers both commit suicide instead of finding each other, being reunited, and living happily ever after.