In "A Retrieved Reformation," why was Jimmy sent to prison?
Jimmy Valentine has a reputation for being the best safe cracker in the profession. He has a lot of connections on the outside, and some of them can get him out of "stir" (also knows as "the big house" and "the slammer") by using their influence, or bribery, with politicians and prison wardens. As "A Retrieved Reformation" opens, Jimmy is getting a pardon after serving "nearly ten months of a four year sentence." The pardon was signed by the governor, who probably took a bribe for doing so, or else was paying back for help in winning an election.
Jimmy has a farewell visit with the prison warden. Jimmy is pretending to be innocent, and the warden, who knows him well, is amused by the pretence. When the warden advises him to go straight and stop cracking safes, Jimmy responds:
"Me?" said Jimmy. "Why, warden, I never cracked a safe in my life."
The warden only laughs and asks:
"How was it you happened to get sent up on that Springfield job? Was it because you wouldn't prove an alibi for fear of compromising somebody in extremely high-toned society?"
So it is obvious that Jimmy was sent to prison this time for a safe-cracking job in Springfield, Illinois. It is also apparent from the warden's dialogue that Jimmy has connections in what he calls "high-toned society." O. Henry doesn't say as much, but it would appear that Jimmy shares some of his loot with crooked politicians and that he might even do favors for important people, such as breaking into safes to steal trade secrets of competitors, or political secrets of rival politicians, or to retrieve documents that might be embarrassing to certain important individuals (as Sherlock Holmes did in a few of Arthur Conan Doyle's stories). Jimmy might even be getting tip-offs from socialites about friends who had valuables in home safes and who were going away on vacation, in which cases he would share the profits with the tipsters.
Jimmy won't admit his guilt, although he knows the warden doesn't believe a word he says.
"Me?" said Jimmy, still blankly virtuous. "Why, warden, I never was in Springfield in my life!"
When Jimmy goes to see Mike Dolan at his bar, we get a little further insight into the machinations that got Jimmy "sprung" from "stir." Evidently this Mike Dolan is the kind of underworld figure who can deliver large blocks of votes through bribery, political favors, finding jobs for people, giving out free drinks, and occasionally using threats or actual force for persuasion. Dashiell Hammett wrote about such a character in great depth in his novel The Glass Key. The mobster's name in Hammett's novel is Paul Madvig. Mike Dolan apologizes for not getting Jimmy Valentine sprung sooner.
"Sorry we couldn't make it sooner, Jimmy, me boy," said Mike. "But we had that protest from Springfield to back against, and the governor nearly balked."
O. Henry spent some time in prison for embezzlement and continued to associate with criminals after he was released. He knew a lot about criminals and underworld characters, and used his experience in many of his stories. He may have inspired Damon Runyon, who wrote very amusing short stories about gamblers, bookies, and other shady characters. O. Henry undoubtedly influenced many American writers.