Why is Jimmy Valentine in jail?
Jimmy had been sentenced to four years in prison for a "bank job" he had committed in Springfield. O. Henry does not provide much specific information about the crime. There are several cities named Springfield in the Midwest. In fact, Wikipedia shows that the name is a common one for towns all over the world. It seems most likely that the "Springfield job" was committed in Springfield, Illinois, which is the state capitol., and that Jimmy received a pardon from the governor of Illinois after serving ten months.
When the warden sends for him to hand him his pardon, the warden also refers to the "Springfield job."
"Let's see, now. 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? Or was it simply a case of a mean old jury that had it in for you?"
When Jimmy goes back to his room to retrieve his suitcase full of specialized safe-cracking tools, he talks briefly to Mike Dolan, who owns the building and runs the restaurant on the ground floor.
“Sorry we couldn't make it sooner, Jimmy, me boy,” said Mike. “But we had that protest from Springfield to buck against, and the governor nearly balked. Feeling all right?”
The crime would have had to occur in the governor's state in order for him to grant a pardon. So the crime must have occurred in Springfield, Illinois, and Jimmy must have been doing time in the Illinois State Penitentiary.
When Jimmy goes up to his room
Everything was just as he had left it. There on the floor was still Ben Price's collar-button that had been torn from that eminent detective's shirt-band when they had overpowered Jimmy to arrest him.
After Jimmy commits three more safecracking jobs in the general vicinity of Illinois, his nemesis is introduced in person.
Ben Price investigated the scenes of the robberies, and was heard to remark:
“That's Dandy Jim Valentine's autograph. He's resumed business.
Jimmy Valentine pulls three more bank jobs after being released from prison: one in Richmond, Indiana, one in Logansport, and one in Jefferson City. There is a Logansport in Indiana, and Jefferson City is the capital of Missouri. Indiana is just east of Illinois, and Missouri is just west of Illinois. This seems to be Jimmy's territory. Then Jimmy may have become aware that Ben Price was on his trail again. He moves to the little town of Elmore in Arkansas and tries to establish a new identity, although he doesn't plan to give up his life of crime. Using his ten months of experience in shoe repair at the prison, Jimmy establishes a shoe shop in Elmore as a "front" and changes his name to Ralph Spencer. He plans to commit his future bank jobs in a whole new area where he is not so notorious.
But fate steps in unexpectedly. Jimmy falls in love at first sight with Annabel Adams, who is the daughter of the president of the Elmore bank. According to O. Henry:
A young lady crossed the street, passed him at the corner and entered a door over which was the sign “The Elmore Bank.” Jimmy Valentine looked into her eyes, forgot what he was, and became another man.
Jimmy's love for Annabel, his success in the shoe business, and his awareness that his fame as a safecracker is putting him in danger of getting caught more frequently and serving much longer sentences, all these factors motivate him to reform. He becomes engaged to Annabel and 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.
But Ben Price shows up in Elmore, ready to arrest him for the three jobs in Richmond, Logansport, and Jefferson City. Jimmy is caught red-handed, breaking into a bank vault and using all his incriminating safecracking tools. If Jimmy was sentenced to four years in prison for a single safecracking job in Springfield, Illinois, it seems likely that he could get twelve years for the three jobs he committed after his release. It is only by a seeming miracle that his reformation is "retrieved."