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
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

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