A Burning Cold Morning (Part 58)

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.  

KSP Eddyville

KSP Eddyville

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:

Brother – 

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. 

1929 Essex sedan

1929 Essex sedan

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

A Burning Cold Morning (Part 57)

Before that trip to prison, however, Leo spent most of the summer doing two things; fencing property for the Schultz gang and running his own separate operation against the city of Louisville.  Due to the influence of the high profile criminals in town Leo understood that he probably should not be running any unsanctioned operations, especially ones that were directed at the city.  Some of those gangsters, including Schultz, had arrangements with various local officials to look the other way in regard to their illegal activities.  Those agreements came with the implicit understanding that these criminals would go easy on the city itself.  Unfortunately for Leo, his usual sense of independence and desire to increase his own standing in the criminal world made it almost impossible to work solely under the direction of Dutch’s operatives.  Instead, he applied for and was swiftly hired into a job at the Louisville city manager’s office (also under the name Robert O’Hara) as an engineer, his falsified degree from Duke apparently never being looked into very closely.  Leo quickly learned the ropes of the operation and within weeks he was diverting newly purchased construction equipment to his own fencing operation and selling it to local contractors.   Things rolled merrily along for him through June and July as Leo made the rounds at the Seelbach’s evening social hour, escorted a rotating cast of women around town and piled up a good amount of cash.  Those funds he kept inside lock boxes in his room and at various other places around town.  

Then on Monday August 13, 1928 he stepped out into a rather cold summer morning and was met on the steps of the hotel by a police officer and city detective.  Leo was arrested for converting stolen property relating to the work he was doing for the Schultz gang and promptly brought to the city jail.  He languished there for several days before an attorney, dispatched by Dutch, arrived and spoke to Leo.  As it turned out, the detective who arrested him was new to the force and not quite familiar with all of the local arrangements in regard to the illegal enterprises being run in the city.  It would have been simple enough to get the whole thing thrown out expect for the fact that there was also new pressure from the city council to clean up some aspects of the criminal element in the city.  That basically meant that Leo was going to have to do some time although it would be a short sentence, just enough to mollify the council.  The attorney encouraged him to, “think of it as a little vacation,” and informed him that all his legal bills were being taken care of by Schultz.

Leo, of course, did not view the situation as any kind of a vacation.  He was focused on making money and improving his reputation and the sentence, one month in city jail, was going to hamper his efforts.  After a day or two of sitting silently in his cell though, Leo’s mood improved and he spent the rest of his time writing letters to women, another to Olivia (that did not mention his location or current situation) and reading up on Duke University.  One of those letters was written to Ginny Mayburn, an auburn-haired local socialite whom Leo spent more time with than any of his other paramours, and highlights his state of mind at the time.

Gin – 

As you’ve surely heard I have landed in the local slammer for a spell – can’t say I enjoy the place much!  Looks like my lucky steak is over but I needed some more time in anyway – it helps make me stand up better with the fellas.  I’m sure I’ll be right back to it next month.  

Free up some time for me around the 20th – I should be out and your company will be just the thing to make me happy.  I’ll be thinking about the night you wore the red satin as I while away my hours in here. 


In what would perhaps be a further reflection that Leo’s luck had gotten thin, during the month that he was incarcerated in Louisville his scheme against the city was exposed.  It only took a few days after he failed to appear for work at the city manager’s office before a new person was hired to replace him.  That man discovered the irregularities (which Leo had not covered up very well anyway), reported them up the chain-of-command and eventually Dutch Shultz became aware of them.  Needless to say, both he and the city officials were not happy that such an operation was being run, and things were put into action to deal with the situation.  

It was yet another unusually cold summer day when Leo was released from the jail.  As he was recovering his personal property he mentioned to the officer on duty how good it felt to be back in, “my proper shirt and suit,” after which he counted the money returned to him three times before signing for it.  He scoffed at the comment made by the officer as he walked away, “see ya soon Bob,” although he would later regret not heeding those words.

Leo was determined to get back into the swing of things quickly, heading straight for the Seelbach after his release.  He was met in the lobby by the hotel’s general manager, an aging man with slicked-back grey hair and a constant smile, who seemed to have been waiting for him. The man informed Leo that due to his extended absence and unpaid bill his belongings had been removed from the room he previously occupied, a statement Leo reacted to with indignation.  The man proved unmoved by the protest and further informed him that he was no longer welcome, although the outstanding bill had been, “taken care of by an interested party.”  After a few more minutes of ineffective protesting Leo stormed out of the Seelbach and walked to the house of a woman named Lucy seven blocks away.  

She at least seemed happy to see him and Leo, spooked by what had happened at the hotel, laid low in her house for the next two days after sending her back to collect his belongings from the manager.  He also contacted two other women, with whom he had secreted other items, and arranged for Lucy to retrieve them.  Once all of it was back at her house Leo packed it into a large trunk, locking it and making her promise to always keep it safe.  It was a calm couple of days, with Leo and her spending much time wrapped up in each others arms.  Then, as evening fell on September 23rd, Leo felt safe enough to venture out on a walk after eating dinner.  He made it two blocks before a police vehicle pulled up behind him and he was arrested again, this time for embezzlement and obtaining goods under false pretenses.  

…to be continued

A Burning Cold Morning (Part 56)

The man seemed to pick up on the implied insult and his cheeks flushed a little bit but he regained his composure after a few shallow breaths.  Leo seemed pleased by the effect of his words.  

“Well, yes I suppose you might think that but people can be more than what you may judge them to be initially.  I have connections here, close ones.  My brother-in-law Otto, it’s his place, well his and his brother Louis I suppose, but he died a couple years ago.  Otto’s had a rough time of it, managing the hotel himself and getting older all the time.  He asked me to come up and help to run this place.”  The clerk’s voice was proud as he spoke although his eyes lacked the strength of his words.  

“You?  He asked you to come up here and help him?  At this fine place?”  Leo’s tone was derisive and harsh.   The man’s ears reddened and he rubbed his hands together nervously before replying.

“Yes, well, yes of course he did.  I have experience you know.”  A short silence followed with Leo drumming his fingers on the desk.  The man looked down and continued talking.  “Well, I suppose that maybe my wife talked him into it.  She’s quite close to him, you know, and worries about his health.  I’m quite capable of doing this though, of working here. Quite capable.”

“I guess we’ll find out then,” Leo replied, “set me up in a nice room.” 

Seelbach Hotel Louisville Kentucky

Seelbach Hotel Louisville Kentucky

And so he was checked in and started a short residency at one of the most popular places in the country for gangsters to visit, play cards, relax and of course, scheme.  Leo felt that he needed to make a strong play for attention from these men and spent most of his remaining money on two things: nice clothes and setting himself up as a fence for stolen goods, hoping to pick up some action from the guests at the Seelbach.  He inflated his credentials and added events to his past experience as he always did, although this time he was careful to follow the false timeline and life story he had developed in Selma.  He made sure that those he talked to had the proper story to bring back to the big-time gangsters. He also picked up several female companions within his first few days in Louisville and promptly fell back into his routine of social outings and romantic interludes.  The letters back and forth with the women also continued and he also wrote to Olivia informing her of his new address.  He was not quite sure why he did that except that he was thinking of her occasionally and it gave him a sense of connection, his only one, to his family and roots.  That seemed to be mattering more to him than it had in the past.  In that letter he also inquired if Stanley was still in New Munich and asked again for a new check to be sent to him.  His current operation was proving quite expensive and he needed all of the money he could get so that he could keep it running and gain a reputation that would get him noticed.  He did not tell Olivia that of course, as he knew it would only make her angry.  He simply stated that the money would come in handy.  

April of 1928 went well for Leo and by the early part of May he had attracted the attention for which he had hoping.  A member of Dutch Schultz’s operation approached him one night at the hotel, pulling him into a corner of the hotel’s restaurant.  They spoke for about twenty minutes, with the man being slightly cagey with details, but making it clear that Leo was being looked at and might be given a test job soon, to see if he measured up to expectations.  Leo walked away from that meeting beaming and positive that the future was looking bright.

Ten days later, and before he had received any kind of a test from the Schultz gang, Leo woke up feeling weak and nauseous, symptoms that got worse as the day wore on.  By seven p.m. he felt poorly enough to ask that the hotel find him transportation to the hospital.   They did so promptly and he was admitted around seven forty-five that night.  The next morning a doctor delivered some unwelcome news to Leo, namely that he had diabetes and it was severe enough that he would need to take medication for the rest of his life.  That did not sit well with Leo, who disputed the idea that he was diabetic and asked to have the tests run again.  When those results came back, confirming the diagnosis, he lashed out, calling the doctor an incompetent fool as the man walked out of the room.  

The real problem of course was that Leo found the idea that he had any medical issues at all to be a blow to his criminal credibility and future plans.  He felt it was a weakness that others would use against him and that would prevent them from looking at him as the big-time boss and gangster that he wished to be.  Also, being sick and weak, especially if that came up during the commission of a crime, was not something that was going to be acceptable.  It was undignified and unbecoming, or that at least is how he described it in a note written to Olivia two day later.  That letter was never sent as Leo really had no wish for anyone to ever know about his diabetes and he vowed to maintain that secret at all costs.  He did accept the medicine from the hospital, or at least he did after initially refusing it and then finding himself back at the emergency room four days later.  It was a fact of life he would deal with while keeping it a secret from everyone.  From that day forward he gave himself shots behind closed doors, spoke little of it (although it would come up and be known during some future incarcerations) and moved on with his plan to be a big time gangster.  Soon after his trips to the hospital Leo was back to running the fencing operation, had passed the test from the Schultz gang and was formulating another scheme that he hoped would bring him a good amount of quick, easy money.  It would be that scheme though which would lead him back into the prison system. 

…to be continued

A Burning Cold Morning (Part 55)

The Selma police never really had much on Leo up to this point.  They knew he was associated with the criminal gang he worked for and had made a note of that along with his connection to Jim Tunney and Max Miller. He had been rousted a few times during police sweeps but they had never made anything stick and always released him after a few minutes of questioning.  It had been on the previous Saturday, the twenty-fourth, that a Be On The Lookout had come across the wire at the station, mentioning a Lee O’Dare and being accompanied by a picture.  Two of the officers recognized the man and had went out to look for him, taking until Monday to track Leo down.  They spotted him walking along a street about three blocks from the boarding house and pulled up alongside.  After a few minutes of discussion by the side of the road they arrested him and booked him into the local jail under the name Lee O’Dare.  

The initial BOLO had been issued from Kansas City, part of a routine transmission from them that also listed several other persons they were looking to find in connection with crimes committed in and around that city.  Leo sat in jail for three days as the Selma police department relayed the information that they had captured the, “requested subject and will extradite upon request.”  The reply came three days later and surprisingly it stated that Kansas City would not seek extradition.  As it turned out, although Tom Pendergast’s control of the police had slackened by this time, he still had the power to get the extradition refused.  He mentioned to a colleague at the time that he, “owed this fella Lee a favor and this’ll be a good time to pay it out.”  

So, Leo was set to be released on Thursday, March 29th as the Selma police still had no solid evidence against him, at least nothing for which they could book and hold him.  He was actually at the counter of the jail, about to retrieve his personal property, when a police sergeant called out from an office down the hallway.

Leo Humbert aka Lee O'Dare

Leo Humbert aka Lee O’Dare

“Just got a notice from Marianna.  Hold up there at the window with that inmate.”  The sergeant then walked down toward Leo holding a print-out in one hand and waving at another officer to accompany him.   Once they were next to Leo the sergeant held up the paper, a wanted notice for Robert O’Hara, suspect in the stealing of a vehicle tag.  Leo recognized the photo, one taken when the Marianna police had briefly held him on a theft charge they had ultimately never been able to prove.  He sighed and shook his head slowly as the sergeant lowered the paper and spoke.

“So, you’re Lee O’Dare here, you’re Robert O’Hara there, that’s a lot of names don’t ya think?” 

Leo did not reply, just staring back at the man who tried again.

“I doubt these are the only two names you have, am I right?”

Again Leo replied with silence after which the sergeant motioned to the officer with him who took Leo’s arm and escorted him back to a cell.  There was bit of a disagreement in the Selma PD after that, with the sergeant and a couple of detectives wanting to keep Leo and see what they could turn up about other names he may be wanted under, and the police chief wanting him immediately sent to Marianna.  The chief won of course and on April Fools Day Leo was transported back down to Florida by the Jackson County Sheriff and and booked into the jail.  Incredibly, the next day when Leo was arraigned, the prosecutor chose to drop all of the charges and he was released before noon into a slightly brisk April day.  As he walked away from the jail, having even received all of his property and money back,  Leo remarked to himself that, “the streak continues!” After that he stole a vehicle, drove to Selma to quickly collect his belongings and cash from the rooming house, and then sped off in a northerly direction.  

He drove without a specific plan other than to put a lot of distance between himself and the south and appears to have wasted little time along the way.  He arrived in Louisville, Kentucky on April 8th and checked into a small motel on the outskirts of the city.  After a little research the next day Leo heard about the Seelbach Hotel and its reputation for being the place to be, especially for a large collection of well-known gangsters including Al Capone.   Excited by the thought of getting up close and personal with just the kind of men he wanted to be like, Leo walked into the hotel at four-forty p.m. that day and approached the registration desk.  He was quite surprised to find, standing behind the desk in a well-tailored but sloppily worn suit, the same diligent clerk who had recorded such detailed observations on Leo when he checked into the motel in Marianna back in September of 1927.  He did not know about those written observations of course but he recognized the man, who had a prominent buck-tooth smile and a deep scar above his left eye, immediately.  The man returned the favor as Leo recovered his wits quickly.

“Hello again sir, and good day.  A bit of a long way from Florida for you, isn’t it Mr. O’Hara?”

Leo winced at this recall of his alias from Marianna as he had intended to use a different one here in Kentucky.   His only consolation was that he felt that also meant he must have made quite an impression on the man.  

“Well, its been a long time since we last met.  A bit of a ways for you also I think,” he replied, making a point to look around the elegant lobby and inferring the man’s previous employment had been in a far less glamorous location.  “It’s really very odd that I should find you here.”

…to be continued

A Burning Cold Morning (Part 54)

Leo had, up to this point in his life, never exactly been a ladies man although he enjoyed their company as much as most other men do.  He usually did not go out of his way to make an impression on them and his preference for nice clothes was more about putting forward the image of a successful gangster than any attempt to catch a woman’s eye.  The interaction with Jim Tunney’s girlfriend though had sparked something inside of him.  He had not made any advances toward her but she had apparently been very interested in him, at least up until the issue with his college degree came up.  Leo caught the idea that maybe he was more dapper and attractive than he had previously thought and so, in his down time and during days off, took to spending more time at social events and speakeasy’s.  A little more bold than before, he found that women did indeed seem to be interested in him and that it would not take much effort on his part to get them into bed.  By the end of January 1928 Leo had on-going relationships with five women and would exchange romantic and sometimes lusty letters with them in-between social excursions and trysts.  He kept every one of their return letters in a shoe box under his bed, a habit of collection that he would continue from then on, often giving up space in a suitcase for them during this later travels.   He was enjoying himself during this period of his life and several times thought back to the times in the past when he had been missing out on all of the fun he was currently having.  One day he even admonished himself that, “good old Stanley Bittenhopper had it all figured out back in Bakersfield, chasing the good times while I stayed home.”  It was a mistake he planned not to repeat in the future.

On February 10th of that year a letter arrived from his sister, one that curiously also mentioned Stanley.

Leo, brother – 

I received your letter and it was good to hear that you are well and doing fine.  Hopefully you understand that I am quite unsettled by having to take part in this ruse with you and the false names.  It is not something I think proper, although you are already aware of my feelings on this matter.   There is, however, a situation to which I object even more and that is having to deal with your criminal friends coming up to our family home to seek you out.  A young man appeared here two days ago, a Stanley Bittenhopper (his true name I suspect although who would know with these types you spend time with), and asked of your whereabouts.  I did not share what I knew with him as for all I know he is looking to find you for bad or notorious purposes.  He plans to stay in New Munich at least from what I can tell as he took a room at the Palmer’s.  He asked that I relay a message when next I was able to contact you, namely that he is wanting to know if you have work for him.  There, I have relayed it as I said I would, although I am certain it implies the worst kind of business and I do not wish to be caught up in this again.  You surely understand and will abide by this wish.  As for your other request, I will discuss the matter of the missing check with the bank and if they advise it to be without risk I will send another.  If not, than you will need to do without that money at least until you next return here, as I fulfilled my obligation in that regard when I sent it the first time.  Perhaps a more permanent address would get your issues with the mail settled in a more satisfactory manner.  Be well brother and know that I wish you the best despite your situation and choices – O

Leo smiley wryly when he was done reading, appreciating the scolding tone and dry humor of his sister.  He was surprised to learn that Stanley had found out where he was from, although he quickly remembered that his former partner knew his real last name and that had undoubtedly made things easier.  He also wondered if there might be a way to put Stanley’s talents to work on his bank robbery plans, although they would first need to discuss the money he had taken from Leo in Pomona.  He wrote back to Olivia, thanking her for her “supreme patience in putting up with her wayward brother,” and asking that she, “tell Stanley that I will keep him in mind and that he should give you his address.  And remind him that he owes me something,” before signing off with, “Your Brother, Leo.”   Right before sealing the envelope he pulled the letter out and added a short post script, informing his sister that she should not worry too much about Stanley as he was a gentle type of criminal.  

Leo continued to have a good run as time moved along into late February, maintaining his work with the local gang while managing his group of lady friends and scheming about bank robbery.  He was making enough money to get by but not nearly as much as he wanted to have, often lamenting that he really had not properly replaced his lost wardrobe.  He wanted to look sharp for the women and also to impress the local criminals, who he though of as beneath him, “lackeys seeking a leader,” as he wrote in one boastful letter to a female acquaintance.  He was confident and proud, certain that he was about to turn things around and would be able to get his own gang up and running soon.  He had even remarked in his journal that he had managed to stay out of the hands of the law for quite awhile despite being involved in several criminal schemes.  The law had chased him, even detained him a few times, but they never made anything stick and he had always been released or gotten away.  That was the mark of a professional he wrote, someone who, “had the edge on the police, someone to be respected.”  Two days later, on March 26, 1928, Leo’s luck changed.  

…to be continued

A Burning Cold Morning (Part 53)

Selma Alabama street scene around the time Leo lived there

Selma Alabama street scene around the time Leo lived there

The Selma, Alabama that Leo had arrived in was one with deep racial divisions and lingering scars from the Civil War battles that had been fought in and around the area.  It carried much of the tone and temperament of the entrenched white majority that had long lived in the area and had an “Old South” feel to it that Leo found foreign to his own experience.  He adapted fairly quickly though and was especially interested in the several banks which occupied a four block area in the downtown of the city.  The two men he had found, Jim Tunnney and Max Miller, who were also interested in the idea of robbing banks were locals and well known to the Selma police department.  Once Leo was sighted hanging out with them he started to gain some extra attention himself although that did little to dampen his enthusiasm for breaking the law.  He really saw himself as a big-time operator and was very interested in branching out into larger crimes.  One day, right after the turn of the new year, he met up with his partners at a local speakeasy.  One of the men had brought his girlfriend along, something Leo was not happy about initially although he changed his mind a little bit later when she starting flirting with him whenever her boyfriend was not paying attention.  After a few drinks all four of them walked out of the speakeasy and down to a local park where they planned to have their first serious discussion about the bank robbery plan.  A stiff breeze was blowing through the park when they arrived and they took some time to find a location that offered a little shelter.  

“You sure it’s ok to talk around the dame?” Leo asked as they all sat down behind a large decorative water fountain in the park.

“Sure, sure,” Jim answered, “she’s been in on a few things before.”  He spoke with a deep Southern drawl that Leo found difficult to understand some of the time.

“Few what?” Leo asked.

“Things,” Jim replied, “jobs, ya know?”  As he answered, the woman, who was his girlfriend and seated behind him, gave Leo a small wink for at least the sixth time that afternoon.

“Well, alright I suppose.  I’ll give you a quick idea of what I’m planning for this thing, just a little bit right now.  You’ll get more details when it’s closer to when we’re gonna do this job.  Until then I’ll be giving you some things to do, to get us ready.”

Max Miller, a man of medium height and dark brown hair cut in a crew-cut style, barked out a short laugh.  “You gonna plan it?  The whole thing, ya think?  Who made you my boss?  or his?”  He finished with a gesture toward Jim.

Leo’s face reddened as he replied.  “This is my thing, my plan.  I’ve had much more experience in this stuff than either of you, I’m sure.  If you’ve got something to say, to add to the plan, bring it up but it’ll be my decision.”  The woman gave him a quick, eager look that seemed to indicate she liked his style of leadership.

“I’m alright with it,” Jim said, “I don’t know much about banks anyhow, that’s for sure.”

“Yeah, but how do we know that he does?” Max replied.  “He’s a nobody around here, we all know it.  New to town and trying to make himself into a boss, how do we know he ain’t just telling tales?  We trust him too much and we could all end up in the clink.”

“Listen,” Leo snapped back, “I know what I’m doing!  I already told both of you that I ran with the Pendergast crew in Kansas City and I was boss of my own operation in Bakersfield.  Maybe you’ve heard of Bob Markword? He’s a friend of mine, a bank robber, ok?”  Leo was upset at having to explain himself and getting very worked up.  “And I’ll have you know I’m a civil engineer myself and spent time on construction jobs at banks.  I know them inside and out so you’ve got nothing to worry about.”  He stopped to take a breath and Max cut in on his rant.

“So, you’re a real civil engineer then?”

“I said I was!” Leo replied defensively.

“Where from?” Max asked.

“What do you mean?”

“Where is your degree from?”

“Wh, what, well,” Leo stammered, somehow unprepared for that question.  He paused a moment and his mind quickly came up with Duke University, a place he had read about in his books as having a respected engineering program.  He replied with that information but it was too late.  Both men had started to walk away and the woman was trailing behind them a little, laughing and pointing back at Leo.  She swayed her hips a final time before hastening to catch up with her boyfriend.  Leo was furious at all of them but also at himself for not having been more prepared and vowed never to be caught out like that again.  He got up and walked back to his room.

When he got there he immediately sat down and sketched out a basic history of his life, at least the one he planned to sell to others going forward.  He made sure to weave in the time and places that would allow for him to have received his degree from Duke and still have all his criminal endeavors, both real and imagined, in place.  Once he had finished with that task he decided to write a letter to his sister and tell her that he never received the check and see if she would send another.  He told her up front about the name he was living under as he felt it would be too risky to try to figure out how to get mail under his real name in Selma.  By the next day he had most of his composure back and was out on the streets, working for the gang while still plotting a bank robbery in his head.  

…to be continued

A Burning Cold Morning (Part 52)

His whereabouts from that day until September 10, 1927 are again unknown, although it would probably be safe to assume that he was traveling by car or train and keeping a very low profile.  Shortly after he disappeared from Pomona the LAPD apparently put together enough information on Leo to make an inquiry back to the Minnesota Bureau of Criminal Apprehension.  They asked for any details that might be available although what response they received, if any, in also unknown.

Marianna FL courtesy mariannaonline

Marianna FL courtesy mariannaonline

What we do know is that on September 10th Leo pulled into a motel in Marianna, Florida and registered under the name of Robert O’Hara.  A surprisingly diligent clerk noted on the registration paper that he “appeared a bit nervous or drunk”, and had asked for a room with, “a clear view of the road.”  It is impossible to know if he was actively running from a crime he had recently committed during his flight from Pomona or if Leo had just picked up a healthy dose of paranoia.  He was given the key to Room #7 and proceeded to settle in to his new base of operations.  

Marianna is a town located in the panhandle area of Florida, a place that in its past had been the location of many plantations due to the fertile soil provided by the Chipola River.  When Leo arrived those days were long gone although farming still remained a major part of the area’s economy.  It was a quiet town, certainly much more tame than the places Leo usually chose to stay, and he may have been hoping to remain undetected in such a rural location.   If that was his intention, his actions while in Marianna would not serve him well.

Once he was settled in at the motel Leo, as usual, started to plot out a way to make money.  He was dreaming bigger than usual and took several days to survey the two banks in the town, taking detailed notes of everything that he observed.  He also found out that there was another bank under construction, one which was due to open in a few weeks, and that fact greatly intrigued Leo.   He had a notion that if he could get some experience and knowledge of what a bank looks like while it is under construction, he may be able to use that to plan out his own successful robberies.  The idea of being able to take a large amount of money on a few jobs and then spend months living good and spending big appealed to him.  It would be much better than trying to muddle along picking up small sums on a large number of jobs, constantly exposing himself to the danger of arrest.  If he realized, or thought at all, about the fact that robbing banks would command much more focused attention from law enforcement, is something we will never know.  What he did do though is attempt to get into the construction site.

To try to accomplish this he entered the site one day and struck up a conversation with the foreman.  He told the man, a stocky and well-tanned Italian-American, that he was a civil engineer and had been asked to look over the building for any potential construction violations.  That statement did not sit well with the foreman who told Leo to leave and come back with written permission to walk the site.  Two days later, Leo tried again and this time the police were called although Leo was gone when they arrived.  After that, getting desperate for money, he returned to some of his usual schemes, this time working with a car theft gang.  

1927 Florida license plate

1927 Florida license plate


1925 Chevy truck

1925 Chevy truck

This particular criminal operation ran two different crews, one that actually stole vehicles and another, the one that Leo ended up working with, that would steal vehicle tags.  This gang was well-known to local law enforcement and kept under close observation when possible.  It only took three months before Leo was seen lifting a tag from a 1925 Chevy truck and pursued by the police.  He did manage to escape although he left everything he owned behind at the motel and arrived five days later in Selma, Alabama.  

His journey of one hundred and seventy-five miles was exactly equal to how much money he had in his pocket and the fuel he could purchase with it.  Completely broke when he drove into town at six o’clock in the evening of December 10th, 1927, Leo’s vehicle ran out of gas on Selma Avenue and he pushed it to the side before abandoning it.  He was exhausted and hungry by this time, neither condition of which he had the means to correct properly, so he walked to the nearest open space he could find and fell asleep under a grove of sugar maple trees.  He awoke in the middle of the night, bothered by some ants that were crawling on his face and the growling of his stomach.  Unable to get comfortable again, Leo sat up until morning plotting what to do next.  

His immediate need was of course money, which he solved temporarily by pawning his gold watch. That allowed him get a meal at a diner and then to rent a room at a boarding house located right at the edge of Selma on Summerfield Road.  He registered as Lee O’Dare, perhaps forgetting about the warrant issued under that name for him in Kansas City, a fact which would almost cause him some trouble later.  Then he took up his usual routine of plotting schemes and seeking out the criminal element in the area around where he lived.  This time Leo accepted that he would need to start small again, and he took up an invitation to be part of a local gang that committed a wide variety of crimes in and around Selma.  He did feel slighted though, having to start all over again despite what he had accomplished in the past.  To try to make up for this, and establish himself properly, he bragged often about his, “time with Pendergast in Kansas City,” and having run his own gang in Bakersfield.  He also spent his spare time scouting local banks and eventually recruited two other men into his scheme to pull off a double robbery.  

…to be continued

A Burning Cold Morning (Part 51)

It took another eight days of waiting but, with Lester finally feeling better and having traveled to the Sleepy Hollow resort area to make the call, the police had the opportunity to put their plan into action.

“Barnett.”  The detective, tall and handsome with thick black hair and sharply cut features, answered the desk phone in his usual clipped manner.

“I’m calling about the investigation into Robert Lester,” Leo stated, “I need to know if he has been found.”

Detective Barnett, who was not assigned to the case but was well aware of the plan, waved at his colleague Dan Robbins.  

“Go ahead, what was that again?” he asked, stalling for a little time.

“You know what I asked,” Leo snapped back, “do you have Lester in custody?”

“Robbins here, this is Leo, isn’t it?” the other detective asked, picking up the second extension.

“Yes, of course, now answer me!”

“Ok, I had to see if it was you.  We try not to give this information out to everyone, you know? It’s been awhile since we heard from you Leo.  I had started to wonder if you still cared about this case.”

“Of course I do, the man tried to kill me!” Leo replied angrily.  “Now, tell me what is going on.”

  “Ok, settle down a bit.  We did finally apprehend him two days ago.”

“Two days? Why wasn’t I notified?” Leo responded angrily.

“Well, I’m sure we would have if we knew where you were.  I’ll come talk to you now though.  Where are you?”

Leo had realized his mistake as soon as he spoke.  “Never mind that,” he said, “so you got him then? That’s good.  Now shoot him and throw the body in a shallow grave.”

Robbins chuckled before replying, “You know that’s not how this goes Leo.  We need you to come in though and give us another statement.  It’ll help get this wrapped up quickly just like you want it.”

“I already gave you a statement, use that.  Are you sure you have him?” Leo asked warily.  “He’s in jail, right in Pomona?”

“Yes,” Robbins replied.

“Let me talk to him.  I want to talk to him.”

“Again, that’s not how this works.” 

“You need to take care of him, get him locked up for good.  He tried to murder me.”  Leo’s voice was rising as he spoke.  “Get him locked up for a good long time.”

“Yes, that’s what we are trying to do, “ Robbins replied.  “Now listen, because like I said, you can help us get this wrapped up.  We need you to come down here.  If you won’t come today then you need to be at the courthouse for sure on Monday, next Monday the first, at nine in the morning, ok?  He’ll be there for arraignment and we may need you to provide some testimony so he doesn’t end up back on the street.”

“Well, I mean, I don’t know, what if you’re just foolin’ me?  Is this some kind of a set up?  Why can’t you use the statement I already gave you?”

“Leo, we have him and if you want him in jail so damn bad you need to be there, ok?”

“Prove to me you have him.  Can I see the, damn, forget that.  How do I know you have him?”

“We’ve been working on this case Leo, for you, to get justice for you.  You’ve called before and we never said we had him, did we?  If we were trying to trick you we would have tried that already.  We just arrested him and now you need to come in and help us convict him.  You need to be there, you understand?”

“Well, ok,” Leo responded in a half-hearted way before slowly hanging up the phone.  

August first was just a few days away and Leo thought about what to do during his entire ride back to Pomona.  By that night he had managed to give himself quite a severe headache from the constant worrying and collapsed into bed hoping to put it out of his mind.  That did not happen and he was back up again at two a.m., pacing his room.  Leo was consumed by the conflict between making sure Lester received full punishment and his fear that the entire thing was a set up.  He wished he had better contacts in Pomona, ones he could check to see if there was a record of Lester’s arrest, but he did not and his need to lay low made any real inquires difficult anyway.  He spent the next two days that way and it was ten p.m. on Sunday when he found himself sitting in his easy chair, exhausted and staring up at the ceiling.  The streets were mostly quiet with the faint sound of a dog barking carrying into his room along with the hum of a radio playing in another part of the boarding house.  Leo was almost there, right on the edge of complete exhaustion, finally about to fall asleep, when a devastating fact occurred to him.  He realized that his call from the Kress building had likely been traced somehow, that the police knew he was nearby and had set up a trap for him.  They did not have Lester after all but were sure to get him if he showed up at the courthouse on Monday.

Energized completely now despite his lack of sleep Leo packed up a valise with his cash and the few items he had purchased since arriving in Pomona and waited impatiently for morning.  Once it arrived, he flagged down a passing oil truck and hitched a ride out of town.

San Bernardino Sun article on Humbert and Lester court appearance

San Bernardino Sun article on Humbert and Lester court appearance

Leo ended up being only partially correct.  The police did in fact have Lester, who had been arrested on July 27th in northern California and brought back to Pomona, and they did bring him to the courthouse on Monday, August 1, 1927.  His arrest had been a fortuitous addition to their plan as it initially was just to lie to Leo and see if they could get him to come in if he thought they had arrested the person who tried to kill him.  Lester had other issues that day in addition to the potential attempted murder charges involving Leo, as the Portland police also came down to serve a warrant on him.  There was also the plan to arrest Leo, both by the Pomona and Los Angeles police, who had sent officers to arrest him for the gas station robbery.  Ultimately though, Lester ended up back in jail and facing extradition to Oregon, while Leo escaped into the unknown thanks to his last minute realization.  

…to be continued

A Burning Cold Morning (Part 50)

Kress Building Pomona California

Kress Building Pomona California

Exactly why Leo thought it would be a good idea to return to Pomona is unknown, but it likely had something to do with his desire to keep track of the investigation into the shooting and Lester.  He realized that he was in danger by returning and vowed to keep a low profile, checking into a boarding house just down the street from the newly erected Kress Building under the name Lee O’Dare.  Knowing that he had enough money to support himself for awhile, he spent most of his time in his room, reading and day dreaming.  When he did venture out he used a variety of disguises and limited how much time he was actually on the street or in other public areas.  He made no friends and brushed off attempts by others to speak with him.  He was very aware of everything around him and would observe the streets outside for long minutes before leaving his room or a store he had reason to visit.  

Leo was actually in more danger than he knew even with his heightened sense of paranoia.  The Los Angeles police detective who had questioned Tom Brinnegan was energetic and resourceful, a veteran of twenty years on the force with a solid reputation for solving cases.  The information he had obtained from Brinnegan made him fairly sure that the Leo O’Malley who had been involved in the robbery was not local to Los Angeles and had likely used a false name.  Also, Leo had slipped up a few times, revealing some small details which would not have meant much except for the fact that Brinnegan proved to be an astute observer and recorder in his own right.  He was able to recount for the detective all of these small facts and that led the officer to start asking around at departments in surrounding communities.  Once he made it to Pomona it did not take long for him and the detectives there to link up the O’Malley and Humbert identities and to conclude that they were likely dealing with the same man.  The two departments agreed to work together in efforts to catch this criminal who had stained both of their communities and also to see what else they could learn about his past history.  All of this had happened in the ten days between the robbery and the day of Leo’s first phone call to the Pomona police department.

He had, of course, thought about it before calling.  He remembered telling the Pomona detective that he was planning to move to Los Angeles but wanted to be kept up to date on the Lester investigation.  He also realized that there was a possibility that his activity in Los Angeles might be linked to his past identity in Pomona, although he thought that was fairly unlikely.  He was confident that he had gone mostly unnoticed while in the bigger city and that Brinnegan knew nothing about him that could identify him.  Mostly though, Leo was driven at this time by his intense desire to see Lester punished for trying to kill him.  That action, that attempted murder, had been a step way beyond anything that Leo was used to or considered to be proper.  He and Lester may have been at odds but they were, after all, fellow members of the criminal world.  There had to be some justice for Leo after such an insult.

Granada Theatre Ontario CA

Granada Theatre Ontario CA

He was careful about it though, hiring a car to drive him to Ontario, California on June 25th and calling back to Pomona from a phone in the lobby of the Granada Theatre.  The conversation was short, with Leo asking for updates and the detective trying to get Leo to say where he was currently residing.  After five minutes Leo hung up in frustration after yelling into the phone, “You better find that murderer and get him locked up!  I’ll be calling you again!” 

That began a game of cat and mouse between Leo and the police department.  While continuing to live at the boarding house in Pomona, he would travel to other cities and call back to the department to insist on updates.   During this time Leo started to have problems sleeping, mostly due to a series of nightmares that replayed the shooting incident, often with the embellishment of his actual death or more prolonged suffering being included.  This lack of sleep eventually led to Leo becoming very ill with a range of symptoms including high fevers, nausea and loss of appetite.  He avoided any interaction with doctor’s as he feared this would lead to his identity being revealed and by July 20th he was weak and delirious along with desperate to get the nightmares out of his head.  Too ill to travel anywhere, Leo could not wait any longer for an update so he walked down to the Kress building, which housed a five-and-dime store, and called the Pomona police from their pay phone.  

1927 Public Pay Phone

1927 Public Pay Phone

That, of course, proved to be a mistake although Leo would not realize it for a couple weeks.  He knew at the time that making the call was not a wise decision but he was so desperate for information that he took the chance, limiting his time on the phone to two minutes.  Although he felt that this was too short of a time for the police to get any useful information on his location, it turned out that the Pomona police were a few steps ahead of him.  Based on some advice from the LA detective, they had alerted all of the city’s operators to take careful note of the origin of all calls requesting the detective section of the Pomona police department.  The operator that day dutifully noted the Kress building as the location where the call came from and the next day the detectives got that information from her.  Realizing that their suspect may well be right back in Pomona, they developed a plan to lure him into the station.  

…to be continued

A Burning Cold Morning (Part 49)

Tom did try to escape, making a break toward the same back office area where Leo had gone, but the officer was telling him to halt or be shot before he made it through the door.  He was taken into custody and, after several hours of unresponsive interrogation, finally told the police most of the truth including that Leo O’Malley had been his accomplice.  A detective took everything down before returning Brinnegan to his cell, stating that he should probably plan on being locked up, “for a good long while.”  

Leo, who had scouted out a secondary escape route to be taken on foot if things went badly, managed to use the alleyways of the area to elude capture.  It had helped that the officer who returned unexpectedly to the station had been alone, and that it took ten minutes for more police to respond to his call for assistance.  By that time Leo was almost a mile away at a city planning commission meeting, an event he had thought might be a good cover during any possible emergency escape from the robbery.  He had actually used the session as part of his planning, a fact he had not shared with Brinnegan, and slipped into the back row just as the chairman called the meeting to order.  He sat their dutifully for the next two hours of discussion, getting sleepy as the adrenaline eased out of his system, nodding off a few times before stepping out to use the restroom.  There, after closing himself into one of the stalls, he got to work.  Breaking the small clasp lock on the briefcase using a pliers he had brought with him, he transferred the money and his now unloaded gun to a black drawstring bag, and then wrapped the briefcase inside a burlap sack.  Stepping outside, he placed the the burlap package behind some large bushes next to the building, tossed his jacket into a trash can and then walked off down the road.  He had taken his glasses off to further alter his appearance, which made for a few challenges as he could not see well without them, but he managed to walk another two miles without incident.  Checking into a nondescript, but not too seedy, motel he drifted off to sleep with the black bag full of money under his pillow.   

The next morning he had some thinking to do.  He realized that he had been fortunate to escape capture the day before and that he was unlikely to get that lucky again.  He did feel a sense of accomplishment despite what had happened, as he felt his back-up planning had went well and he had anticipated possible problems.  The pliers, burlap sack, secondary escape route and hiding in plain view at a public meeting were all things he was sure he would not have thought of earlier in his criminal career.  He was becoming more accomplished and that made him feel good, plus he had all of the robbery money to himself.  Leo knew though that Brinnegan would give him up, in fact he probably already had, and that he needed to inconspicuously leave the area very quickly.  



Leo pondered all of this while sitting at a small diner that was associated with the motel, and he was interrupted by a small, thin man who was sitting at the table next to him.

“Hey friend, hey, hello, hello.”  

Leo shook his head, realizing that someone was talking to him.  He looked over and saw the man, dressed in a blue suit and white shirt, a red necktie hanging loosely around his neck.  

“What?” Leo replied.

“You, I was just trying to get your attention but you were way, way off in your dreams, I think?”  The man spoke in a rushed, clipped manner and his voice tended to squeak a little at the end of sentences.  It was fairly irritating.

“I’m thinking, not dreaming.  Leave me alone.” Leo turned his head away as he spoke.

“It’s ok, ok, no problem.  I just figured, you know, just wanted to make sure you were ok.  You were staring off into space for a long time, long time, maybe ten or fifteen minutes.”

“What’s that to you?” Leo snapped back.  “Leave me alone.”

The man inched his chair a foot closer to Leo, blocking the aisle way between the tables.  “Ok, ok, I just thought that maybe you were, you know, like me, out on the road too much and thinking of home.  I do that a lot, you know, a lot of thinking about home.  It’s hard to be out on the road so much isn’t it?
“Who said I’m out on the road?” Leo asked.

“Well, I guess, well I did, you know, because I thought you might be, I am.  I am on the road a lot.”  

Just then a waitress approached and the man had to slide the chair back toward his table.  Leo hoped that would be the end of it, but it was not.  As soon as she had sauntered past, poured coffee two tables away and then walked back, the man pulled his chair right up next to Leo.

“Like I was saying, I’m on the road all the time, all over the place.  Just leaving here today and gotta go to Pomona next, then San Bernadino, Palm Springs, it never ends you know.  But you know, you know, right?  You’re a salesman too, I bet.  What’s your product?”

Leo was very annoyed at this point but had heard one thing that caught his attention.  

“You say you’re going to Pomona?”

“Yes, yes, you going there too?  Maybe we can meet up after the day, you know, have a drink or dinner?  What’s your line, anyway?  Vacuums?”

“Actually, I’m needing to get to Pomona myself.”  Leo was thinking quickly as he spoke.   “My vehicle broke down here the other day, gonna take a few more to have it ready I guess.  You wouldn’t mind giving me a ride, would you?  I could pay for gas, I’ll even buy your breakfast.”

Pomona 1927

Pomona 1927

The man, who then introduced himself as Chuck Creely, eagerly accepted and then talked Leo’s ear off all the way to Pomona.  Leo never did mention what he might be selling or why he needed to get to Pomona, but Creely hardly seemed to care as it was clear he was just lonely and wanted to talk.   When Leo was dropped off, with a false promise to meet up for dinner at five o’clock, he almost felt bad for the man.

…to be continued