In 1916, vast portions of rural Texas and Oklahoma were still very much like the wild days of the Old West.. Sam Bass had been shot and killed 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. All the Dalton brothers were gone except for Emmett Dalton, who had survived 23 gunshot wounds in the ill-fated double bank robbery in Coffeyville, Kansas, in 1892. He served 14 years in a Kansas prison and later moved to California. , where he became a true Western realtor, storyteller, author, and actor. He died in 1937 at the age of 66.
At the time of the bank robbery, Willis did not know 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 American history. According to Willis, he was “trying to learn to drive” in the Boswell assault.
It was in Durant, Oklahoma, that Willis encountered a loose gang of bank robbers. One of them asked him if he wanted to work in a bank in daylight. “Hell yeah,” Willis told them and they introduced him to two men he’d be working with on the Boswell robbery.
In his last interview in 1979, he described his first bank robbery.
“One was a tall thin boy named Charlie Rankins and the other guy, I don’t remember his name, but his face was scarred, probably smallpox or something. They had horses and we planned the Boswell bank job; it was about 15 or 20 miles on this side of Hugo.
“The bank was the last building in town when you left, nothing but bushes after that. They had some trees there where you could tie up horses. Well that’s what we did; one day we went to Boswell and tied the horses in the bank Nobody 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 stayed up front, Charlie and the other boy ran after and started looting the money. Charlie took all the money out of the safe and the other boy cleaned out the cash drawers. They made it to $ 10,000. We told everyone. to stand still or we’d blow their heads off. So big as you like, we unleashed our horses and trotted slowly into the undergrowth. No one left the shore when we looked back.
“We headed across the South Boggy River and followed the river to the outskirts of Hugo, where we divided the money. I give you my horse and my saddle and said, ‘Folks, go on and I’ll go to Hugo tonight fishing.’ I get a train from here. I assumed they weren’t looking for anyone to catch a train but three men on horseback. I knew there was a passenger train leaving there sometime after 10 o’clock, so I I stayed in the undergrowth until it got 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 my coat on, you didn’t know I had it in my pockets or whatever. Just before 10 o’clock I went in there and bought myself a ticket to Ardmore, as fancy as you want. It was clear after I got to Ardmore. “
About a month after the Boswell robbery, Charlie Ranking was arrested when they found a quantity of silver dollars on rolls of paper with the bank’s name on it. When Willis learned that his friend was in jail, he devised a plan to get into jail and see if he needed help. I knew a man in Hugo who had been a pigeon in jail. Visiting the man, he boasted that there appeared to be several easy benches in the area that “needed to be knocked 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 imposing on me. They grabbed me and put me in jail, which was just what I wanted. So I was able to talk to Charlie and I said, ‘Do you want me to help you? I can come in and kick you out if you want. “
“No, heck,” he said. “I don’t think they have much on me, not enough to put me in the penitentiary. They will bail me out in three weeks.”
“They kept me in jail for three or four days and they just wouldn’t let me loose. They could keep you in jail for as long as they wanted, on those days. Finally, I had to go find a lawyer and pay them $ 250 to get out of the house. Later, I found out that Charlie was sent to McAlester Penitentiary for 25 years. I never saw him again.
“My share of the robbery was around $ 4,000, but I didn’t have it when I went back to Hugo. I had come to San Antonio and I put six or seven hundred in the bank and gave the lawyers a Check in the San Antonio bank to get me out. Good. 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 says, ‘Well, wait here a minute.’ He took it and He went back there and I saw him talking to someone and I knew they were going to arrest me. So I went and went to Uvalde and I gave a lawyer a check for all my money, and he went 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 whatever they wanted to you.
“The bank at Boswell was the first daylight job I did for money. But I didn’t hesitate. Hell, if you hesitate, you’re likely to get in trouble. If you’re going to do something like that, you better do it. He was always saying, ‘Come on, guys,’ and I took the lead and we never stopped for nothing. The bank robbery in Winters, Texas, with Frank, the old bank robber, was my first night job. However, $ 3,500 in Liberty bonds from there, and they killed that kid next to the car. So I never got any of that. He had the bonds in his hip pocket, the one who was killed. “
Willis’s version of his first bank robbery refers to a failed nightly 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 they could blow out with nitroglycerin. His source was a Bankers Association detective named Boyd, who wanted a share of the loot. It turned out that after the vault door was blown off, the money was kept in a round safe that they couldn’t open. After looting the vault, they finally left with $ 3,500 in Liberty bonds.
Back in Abilene, a third man named Al was driving an early Hudson model 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 next night, when they entered Buffalo Gap. Just as they were approaching town, a car full of law enforcement officers passed them on the road. When 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 barrage of shots, Al was shot in the chest and fell. Frank then took off in a different direction into the brush. It was the man named Al who was wearing the restraints when the gang shot him dead.
Willis managed to escape, but was later captured with his friend Red, near Sweetwater. They were incarcerated at Ballinger with Slim Edgarton, who had been captured earlier. After bribing the sheriff’s wife, the trio managed to escape from jail in the middle of the night and escape.
Willis, who repeated a pattern he would use throughout his career, returned to San Antonio after work at Boswell and then headed to the family home in Uvalde. In 1916 he was still “learning the ropes” of outlaw life, while, with the exception of his brothers Jess and “Doc”, the rest of the family were engaged in honest work as ranch laborers or scrabble sharecroppers, known in West Texas as “cyclonic farmers.”
Later, Willis and some of his brothers formed the Newton Gang, which robbed more than 80 banks in Texas, the Midwest, and Canada in the early 1920s.