In 1916, vast portions of rural Texas and Oklahoma were still very similar to the wild days of the Old West.. Sam Bass had been shot to death in a bank robbery in Round Rock, Texas, 38 years earlier. Jesse James had only been buried for 34 years. Thomas E. Ketchum (Black Jack Ketchum) had been hanged in 1901 for attempted train robbery. Robert LeRoy Parker (Butch Cassidy) and Harry Longabaugh (Sundance Kid) were reported to have been murdered by Bolivian police in 1908. Frank James had died the year before (1915), spending his last days giving 25-cent tours of the James . ‘ farm in Missouri. The Dalton brothers were gone except for Emmett Dalton, who had survived 23 gunshot wounds in the unfortunate double bank robbery in Coffeyville, Kansas, in 1892. He served 14 years in a Kansas prison and then moved to California, where he became a real estate agent, storyteller, author, and western actor. He died in 1937 at the age of 66.
Little did Willis know at the time of the bank robbery that in his lifetime he would rob more banks and trains than all his predecessors combined. He and his brothers still hold the record for the most money stolen from train robberies in United States history. According to Willis, he “was just trying to learn the ropes” in the Boswell heist.
It was in Durant, Oklahoma that Willis encountered a gang of bank robbers. One of them asked him if he wanted to participate in a daytime banking job. “Hell yeah,” Willis told them and was introduced to two men he would be working with on the Boswell robbery.
In his last interview in 1979, he described his first bank robbery.
“One was a tall, skinny boy named Charlie Rankins and the other guy, I can’t remember his name, but he had scars all over his face, probably from pox or something. They had horses and we planned the Boswell bank work; it was like 15 or 20 miles on this side of Hugo.
“The bank was the last building in town when you left, nothing but brush after that. There were some trees there where you could tie horses. Well, that’s what we did; we went to Boswell one day and tied the horses in the bank no one knew me there so i went in and acted like i was getting change charlie and the other guy came in while i was talking to the teller pat because we were robbing the bank
“While I was holding the front, Charlie and the other guy ran behind and started looting the money. Charlie took all the money out of the safe and the other guy cleaned out the cash registers. It came to $10,000. We told everyone Let them stay or we’d blow their goddamn heads off. Then, as big as you wanted, we untied our horses and trotted slowly into the brush. No one left the bench when we looked back.
“We crossed the South Boggy River and followed the river to the outskirts of Hugo, where we split the money. I gave them my horse and saddle and said, ‘You guys go ahead, I’m going to go to Hugo tonight and catch me a train of here. I assumed they weren’t looking for anyone to catch a train, they were looking for three men on horseback. I knew there was a passenger train leaving there sometime after 10 o’clock, so I stayed outside in the undergrowth until dark.
“They took all the hard money (silver) and gave me green money (cash) for mine, so I put it around my waist and folded a little in my pocket. When I put on the coat you couldn’t tell I had it in my hands.” pockets or anything. Just before 10 o’clock I went in there and bought a ticket to Ardmore, fancy as you like. It was clear after I got to Ardmore.”
About a month after the Boswell robbery, Charlie Ranking was arrested when they found a number of silver dollars in rolls of paper bearing the bank’s name. When Willis found out that his friend was in jail, he devised a plan to break into the jail and see if he needed help. He knew a man in Hugo who had been a snitch in prison. Visiting the man, he bragged that there seemed to be several easy benches in the area that “needed to be taken down.”
The man immediately went to the police and reported his conversation with Willis.
“When I went down to the station that night to catch a train, the law was on my side. They caught me and put me in jail, which was just what I wanted. So I talked to Charlie and said, ‘Do you want me to help you? ? I can come in and kick you out if you want.”
“No, hell,” he said. “I don’t think they have much on me, not enough to put me in the penitentiary. They will be setting my bail in three weeks.”
“They kept me in jail for three or four days and they just wouldn’t let me go. They could keep you in jail as long as they wanted, in those days. Finally, I had to go find a lawyer and pay them $250 to get out of jail.” I later found out Charlie was sent to McAlester Penitentiary for 25 years I never saw him again.
“My share of the robbery was about $4,000, but I didn’t have it with me when I got back to Hugo. I had come to San Antonio and put six or seven hundred in the bank and give the lawyers a check at the San Antonio bank to get me out. Well, about two months after that, I went to San Antonio to withdraw the rest of my money and they had the law waiting for me. I had written a check to get my money and this teller is like, ‘Well, wait here a minute. ‘ He took it and he went back there and I saw him talking to someone and I knew I was going to get arrested, so I just left and went down to Uvalde and gave a lawyer a check for all my money, and he was out there the next day. and I got it. I never knew why they wanted to arrest me, but that’s what they were planning to do. They arrested you for nothing in those days. They would do what they wanted with you.
“The bank in Boswell was the first day job I ever did for money. But I didn’t hesitate. Hell, if you hesitate, you can get in trouble. If you’re going to do something like that, you better do it.” . She always told them, ‘come on guys,’ and I took the lead and we never stopped for anything. The bank robbery in Winters, Texas with Frank the old bank robber was my first night job. We never got but $3500 worth of Liberty bonds out of there though, and they killed that old man by the car. So I never got any of that. He had the bonds in his back pocket, the one that was killed.”
Willis’ version of his first bank robbery references a botched late-night robbery in Winters, Texas, where he and three others broke into the bank at midnight. Frank, a friend of his, had been told that Winters Bank had a vault that could be blown up with nitroglycerin. His source was a Bankers Association detective named Boyd, who wanted a piece of the loot. It turned out that after they blew up the vault door, the money was kept in a round safe that they couldn’t open. After looting the vault, they finally walked away with $3,500 in Liberty bonds.
On the way back to Abilene, a third man named Al was driving an early model Hudson when the car got stuck in the sand and burned out the clutch near Buffalo Gap, Texas. They abandoned the car and hid in the hills until the following night when they walked towards Buffalo Gap. Just as they neared the city, a car full of law enforcement officers drove past them on the road. As the car stopped and turned around, Willis and his friend Slim Edgarton ran into the brush while Frank and Al stood their ground shooting at law enforcement officers in the car. After a flurry of gunfire, Al was hit in the chest and fell. Frank then went in a different direction into the brush. It was the man named Al who was wearing the restraints when the gang shot and killed him.
Willis managed to escape, but was later caught with his friend Red near Sweetwater. They were jailed at Ballinger with Slim Edgarton, who had been captured earlier. After bribing the sheriff’s wife, the trio managed to break out of jail in the middle of the night and escape.
Repeating a pattern he would use throughout his career, Willis returned to San Antonio after the Boswell job and then headed to the family home in Uvalde. In 1916 he was still “learning the ropes” of life outside the law while, with the exception of his brothers Jess and “Doc”, the rest of the family were engaged in honest work, working as ranch hands or tough sharecroppers, known in the West. Texas as “cyclone farmers.”
Willis and some of his brothers would later form the Newton Gang that robbed more than 80 banks in Texas, the Midwest, and Canada in the early 1920s.