There is not any conclusive evidence as to when Leo first started to experiment with changing his name. He would use several aliases throughout his criminal career and it is likely that he began the practice before he left New Munich for the first time. There are a few records, old and difficult to accurately assess, that seem to indicate that he used the name Lee O’Dare (a play on his first name) at some point in the mid-1910’s while he was still in school. These references are on documents from the Sauk Center and Meier Grove areas where he may have been picking up work in the summer. It would appear from the records available in New Munich that he was still going officially by Hombert when he graduated from Saint Boniface Catholic School in 1918. After that the trail of the name Hombert stays in New Munich with his family while that of Leo starts to go in a different direction. Soon after his graduation, Leo enlisted in the United States Army under the name Humbert and served in the Quartermaster Corps until 1920. During that service he ended up in Hawaii and it is there that he began to commit more serious crimes and where he also met a man with whom he would cross paths again in later years. That man, Robert F. Lester, would in fact try to kill Leo in the late 1920’s, although they started out as true brothers-in-crime.
It was the beginning of 1920, January 12th, when Leo first met Robert in the mess hall of the Army fort where they were both stationed. The fort was a large one and the mess hall was always busy, with seating hard to come by during the peak breakfast and dinner hours. You pretty much had to grab an open space wherever you could find one and on this day Robert did just that, grabbing a open spot next to Leo just after a sergeant stood up to leave. After a few minutes of silent eating, Robert asked Leo if he was going to attend the movie that night in the airplane hanger. He was met with silence, which did not discourage him as he was one of those overly-talkative kinds of people who seem impervious to social signals telling them to leave people alone. Robert launched into a monologue on his opinion about the movie, The Valley of the Giants, which he had seen four times already and which he thought was a terrible film. He did seem to think that Grace Darmond was quite excellent as Shirley Summer but the rest of the cast “stunk it up.” Leo did not reply to any of it although a few others at the table jumped into the conversation, most of them agreeing about the general quality of the movie and wondering why the Army insisted on showing it to them every few months. Somewhere during that discussion Leo slipped away, his tray neatly returned to the kitchen wash line before Robert noticed the vacant seat across the table, one that was then immediately filled by another man. Ten days later he passed Leo in the courtyard outside the supply office and tried to speak with him again.
“Hey there, you remember me?”
Leo looked over his way, seeing a tall, olive skinned man with jet-black hair and a wide, open face approaching. The man walked with a small limp and had arms that swung too much as he walked. Leo shook his head and kept walking.
“Hey there, quiet man, I’m talking to you!” the tall man called out, “you there, stop for a minute.” By then the man was walking abreast of Leo and pulling at his sleeve.
“What do you want?”
“I’m just trying to talk to you for a minute. Don’t you remember me? From the other day in the mess hall? We were talking about movies and I,”
“Yes, I certainly do,” Leo interrupted, “and I’m hoping to not get another dose of it right now.”
“How about you there, you’re not a very nice egg are you?”
“I’m plenty nice but not to every random person I meet.”
“It don’t hurt you none to talk to people, does it?” The tall man patted his pockets quickly then continued. “Butt me, will ya? I’m out.”
Reluctantly Leo reached into his pocket and pulled out his cigarettes, offering one to the man with a look of displeasure.
“See there, you’re not so bad after all. Robert Lester by the way.” He stuck out his hand, which Leo took without offering his name in reply. He started to step away but the man grabbed his arm.
“No rush, what could it be? Nothing around this place these days needs that much of a hurry attached to it. Why don’t you smoke with me?”
“Why would I?”
“Well, it’s the friendly thing to do and I might have something interesting to say.”
“Judging from the last time I would doubt that,” Leo replied, although he did have a slight smile on his face now, which Robert picked up on.
“See there, you’re better already. Now, let’s talk about making a few clams together.”
It was there, in the courtyard of an Army fort, that Robert Lester outlined in a low voice to Leo Humbert a scheme that would ultimately land them both in prison, although it would also make them a good amount of money for a short amount of time. Robert was a truck driver in the motor pool, a man who drove large delivery vehicles all over the island on a daily basis. Leo was a part of the quartermaster’s department, and had access to quite a large amount of inventory. Those items were desired by various groups and organizations out in town and also at ports around the islands, and people were ready to pay for them. Robert knew those people and could facilitate the deals. All he needed was a partner on the inside of the quartermaster department. Leo, who had been glancing around nervously as Robert spoke, shook his head slowly when he finished.
“I can’t do it.”
“It’s too dangerous. Besides, you don’t strike me as the safest person to do business with anyway. You talk too much and too openly. I mean, look at where we are right now.”
“No one can hear us, there isn’t anyone else here. Trust me, I know my onions on this, we can make good money.”
“Why ask me anyway? I could just as easily turn you in.”
“I doubt it.”
“You’re already selling supplies yourself, you’re just not very good at it.”