Leo was held again in the Louisville city jail, much angrier this time but still taking the opportunity to write letters to various women. He knew that he needed to speak with Lucy in regard to the trunk and also tried to convince at three different women to come and visit him, all of whom refused to be seen in such a place. No attorney was dispatched to assist him this time and after a few attempts to reach out to contacts on the outside, all of which were rebuffed, he realized that he was going to face his current charges alone. Although he could have arranged for some of his hidden money to be used to hire a powerful lawyer, Leo had correctly deduced that no manner of defense was going to save him, and that the upcoming trial was going to be a mere formality. For that reason, he chose to conserve his funds, finally convincing Lucy to come to the jail so he could whisper some more specific instructions to her about what to do with his stash while he was away. On October 21st Leo’s trial began and he was convicted before the close of business the next day, represented by a public defender who barely raised an objection during the entire trial.
Two days later he was processed as a new inmate (#5958) to the Kentucky State Prison at Eddyville and began to serve his one year sentence. His time there is mostly undocumented, although several facts are known. Leo immediately got back into the routine of inflating his criminal background and accomplishments, weaving into his story the new information of his recent, “stint with the Schultz gang.” He made few friends but the ones he did associate with were all convicted bank robbers and Leo grilled them for information whenever he had the chance. He even began to plan a robbery with one of these inmates, although that person turned him into the warden, resulting in Leo spending two weeks in solitary confinement. He also wrote letters to several female acquaintances, again asking for and being rebuffed in regard to visiting him, and sent one letter to his sister Olivia. In addition to asking a few questions about how she was doing, Leo inquired as to whether she knew the location of Stanley Bittenhopper and if his former partner had done anything to betray him. Her return letter to him was recovered and reads as follows:
I am well, thank you for asking, and things are about as quiet and peaceful as you might imagine them to be in New Munich. Although it is good to hear that you are well, it is apparent that you are determined to continue to involve me in your shady business. I have already expressed my distaste for your name games and your current alias is no better than the previous. You will, however, see that I have (begrudgingly I assure you) addressed the envelope to you, Mr O’Hara!
Another item I must point out is that it cannot possibly have escaped your attention that, despite what I must assume was an attempt to conceal the fact, your last letter is clearly postmarked from a prison in Kentucky! What foul thing you done to be incarcerated in a place such as that, well, I refuse to think of it. Your associate Stanley has stayed here in town but away from me, thank heavens, and I have no information on what he may have or have not done in regard to his intentions toward you. He did approach me one day in town to hand me an envelope, saying I was to inform you that his debt has been paid. There, you see I have now become a go-between in your criminal mischief, a turn of events that distresses me greatly. I will have your little package for you, if you ever choose to retrieve it, as I feel honor-bound to deliver it to you.
Do not ask again about your check – I will not be replacing it as I can receive no information that satisfies me it cannot be cashed later.
Despite my displeasure brother, know that I wish you well – O
Leo appears to have had no disciplinary issues other than the one associated with his time in solitary and the only other incident of note was a brief stint in the medical ward for issues related to his diabetes. An appeal undertaken on his behalf (by a lawyer he hired with his own money once he figured no one was paying attention to him anymore) managed to get his sentence slightly reduced and Leo was released from Eddyville on August 16, 1929. During the out-processing that day his suit, which he had been wearing when arrested, could not be found, a discovery which set Leo off onto a three minute rant on police incompetence. He had to walk out of the prison that day wearing some over-sized prison issue work pants and a shabby shirt provided from the prison’s “missionary basket.” That fact did nothing to improve his mood and Lucy, who had picked him up, heard about it all the way back to her place.
As per what appeared to be his usual routine whenever he was released from custody, Leo quickly hit the road and disappeared for awhile. He had recovered most of his stashed money before he left, along with several good suits and a few other personal items.
It is not known when he decided on his ultimate destination but on September 1 he rolled into New Munich driving a brand new Essex sedan. He proceeded to check into a motel, doing so under the name of Hombert. Leo knew that the whole town would soon know he was back in the area and it would be very hard to explain the use of any of his aliases without arousing suspicion. It would probably also be convenient to use that name in that it was largely unknown to law enforcement. He used some of his money to buy new suits and two hats and the next day went to see Olivia. She turned over Stanley’s package, which included the money that had been stolen plus interest along with a short note of apology.
…to be continued