In 1916, vast portions of rural Texas and Oklahoma were still very similar to wild days of the Old West. Sam Bass had been shot up 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 killed by the 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 all gone except 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 then moved to California where he became a real estate agent, raconteur, author, and Western actor. He died in 1937 at age 66.
At the time of the bank robbery, Willis did not know that over the course of his life he would rob more banks and trains than all of his predecessors combined. He and his brothers still hold the record for the most money stolen in train robberies in U.S. history. According to Willis he was “just trying to learn the ropes” in the Boswell holdup.
It was in Durant, Oklahoma that Willis met up with a loose-knit band of bank robbers. One of them asked him if he wanted in on a daylight bank job. “Hell yeah,” Willis told them and he was introduced to two men he would work with in the Boswell robbery.
In his last interview in 1979, he described his first bank holdup.
“One was a tall, slim boy named Charlie Rankins and the other guy-I don’t recall his name but he had a face full of scars, probably smallpox or something. They had horses and we planned up the Boswell bank job; it was about 15 or 20 miles this side of Hugo.
“The bank was the last building in town as you were leaving, Nothing but brush after that. They had some trees there that you could tie up horses. Well, that’s what we done; one day we went over to Boswell and tied up the horses at the bank. Nobody knowed me there so I went on in and acted like I was getting change. Charlie and the other feller come on in as I was talking to the cashier. I threw down on him and hollered for everybody to ‘stand pat because we was robbing the bank.’
“While I kept the front, Charlie and the other guy run around behind and started sacking the money. Charlie got all the money out of the safe and the other guy cleaned out the cash drawers. It come to $10,000. We told everybody to stay put or we would blow their damn heads off. Then big as you please we untied our horses and slowly trotted off into the brush. Nobody come out of the bank when we looked back.
“We headed across the South Boggy River and we followed the river to just outside of Hugo where we split up the money. I give them my horse and saddle and said, ‘You fellows go on and I’m going into Hugo tonight and catch me a train out of here.’ I figured they wasn’t looking for no one to be catching a train, they was looking for three men on horseback. I knew there was a passenger train that left there sometime after 10 o’clock, so I stayed out there in the brush ’til it got dark.
“They took all the hard money (silver) and give me green money (cash) for mine, so I put it around my waist and folded some in my pocket. When I put my coat on you couldn’t tell I had it in my pockets or anything. Just before 10 o’clock come I walked in there and bought me a ticket to Ardmore, slick as you please. It was clear sailing after I got to Ardmore.”
About a month after the Boswell robbery, Charlie Ranking was arrested when they found a quantity of silver dollars in paper rolls bearing the bank’s name. When Willis learned that his friend was in jail he devised a plan to get inside the jail and see if he needed help. He knew a man in Hugo who had been a stool pigeon in prison. Visiting with the man, he boasted that there seemed to be a number of easy banks in the area that “needed to be knocked over.”
The man immediately went to the police and reported his conversation with Willis.
“When I went down to the depot that night to catch a train, the law was laying for me. They grabbed me and put me in jail, which was just what I wanted. So then I got to talk to Charlie and I said, ‘You want me to help you? I can come in and turn you out if you want me to.’
“No, hell,’ he said. ‘I don’t think they’ve got much on me, not enough to put me in the penitentiary. They’ll be setting my bond in three weeks.’
“They kept me jailed for three or four days and just wouldn’t turn me loose. They could keep you in jail just as long as they wanted to, in them days. Finally, I had to go get a lawyer and paid them $250 to get out of jail. Later on, I found out they sent Charlie to the penitentiary at McAlester for 25 years. I never did see him again.
“My cut from the robbery was right around $4,000, but I didn’t have it on me when I came back to Hugo. I had come down to San Antonio and put six or seven hundred in the bank and I give them lawyers a check on the San Antonio bank to get me out. Well, about two months after that I went down to San Antonio to draw the rest of my money out and they had the law waiting for me. I had wrote a check to get my money and this teller says, ‘Well, wait here a minute.’ He took it and went back there and I seen him talking to somebody and I knowed they were going to arrest me. So I just walked off and went down to Uvalde and give a little lawyer a check for all of my money, and he went up there the next day and got it. I never did know what they wanted to arrest me for, but that’s what they was fixing to do. They arrested you for nothing in them days. They would do anything they wanted to you.
“The bank in Boswell was the very first daylight job I ever done for money. But I didn’t hesitate. Hell, if you hesitate you’re liable to get in trouble. You go to do anything like that, you better do it. I always told them, ‘Let’s go boys,’ and I took the lead and we never stopped for nothing. The bank robbery at Winters, Texas, with Frank, the old bank robber, was my first night job. We never got but $3,500 in Liberty bonds from there, though, and they killed that one old boy there alongside the car. So I never got nothing out of that. He had the bonds in his hip pocket, the one who got killed.”
Willis’ version of his first bank hold up has a reference to a botched night time robbery in Winters, Texas, where he and three others broke into the bank at midnight. Frank, a friend of his, had been told that the Winters bank had a vault that they could blow with nitroglycerine. His source was a Banker’s Association detective named Boyd, who wanted a cut of the loot. As it turned out after they had blown the vault door, the money was stored in a round safe that they could not open. After ransacking the vault they finally left with $3,500 in Liberty bonds.
Heading back to Abilene, a third man named Al was driving an early model Hudson when the car got stuck in sand and burned out the clutch near Buffalo Gap, Texas. They abandoned the car and hid out in the hills until the next night when they walked into Buffalo Gap. Just as they neared the town, a car full of lawmen passed by them on the road. When the car stopped and turned around Willis and his friend, Slim Edgarton, ran for the brush while Frank and Al stood their ground shooting at the lawmen in the car. After a volley of shots Al took a slug in the chest and went down. Frank then took off in a different direction into the brush. It was the man named Al that had been carrying the bonds when he was shot and killed by the posse.
Willis managed to escape but was later caught with his friend Red, near Sweetwater. They were jailed in Ballinger with Slim Edgarton, who had been caught earlier. After bribing the sheriff’s wife, the trio managed to break out of the jail in the middle of the night and get away.
Repeating a pattern he would use throughout his career, Willis returned to San Antonio after the Boswell job and then headed for the family place in Uvalde. In 1916 he was still “learning the ropes” of the outlaw life while, with exception of his brothers Jess and “Doc”, the rest of the family was engaged in honest labor-working as ranch hands or hard scrabble sharecroppers, known in West Texas as “cyclone farmers.”
Later, Willis and some of brothers would go on to form the Newton Gang that robbed over 80 banks in Texas, the Midwest, and Canada during the early 1920s.