On December 29, 1914, Willis robbed his first train, at age 25. He had just been released from serving time in prison and met up with an old friend, Red Johnson. The two had gone to Uvalde and while there had broken into a hardware store to steal some Winchester 30-30s and ammunition for a pistol Willis was carrying. They decided to go to Cline, a small settlement west of Uvalde, by foot the day after Christmas with the intent of robbing the Southern Pacific Number 9 passenger train that passed through the station around midnight.
In his last interview in 1979, he described his first train robbery:
“Just after Christmas, me and Red Johnson set off for Cline (Texas) by foot. I knowed the Number 9 train came in there about midnight and took on water. So I told Red, ‘Let’s rob that train tonight.’
“That night we went down to a little freight house near the depot. While we was waiting we took the linings out of our big overcoats to cover our heads and use as masks. When the train came in that night, we hit the back of it.
“An old brakeman hollered at us and said, ‘Hey! You can’t get on here!’
“I told him, ‘Like hell we can’t,’ and I jabbed that pistol in his belly and he changed his tune. He didn’t give us no trouble. We went in to the first car that was a special car for the superintendent of the Southern Pacific Railroad, old man Watkins. He was in there with another fellow. Watkins had a big old thick pocketbook and we thought we had a wad of money. Damned if his pocketbook wasn’t full of them railroad passes and 40 measly dollars!
“We went on up through the Pullman cars. We ain’t never been in a Pullman car so we didn’t know about them berths upstairs too. We just got the ones on the bottom and went through two of them. If we come up on a woman by herself we let her go.
“When we come through the first car, we didn’t know there was a drawing room in there with a rich old Mexican riding with his daughter. Sure enough, they had several thousand in cash and $15,000 in jewelry in a little bag up there. They was in a compartment car and we didn’t know nothing about that so we passed them up.
“Getting close to Spofford, we pulled the cord, stopped the train, and got off. In a few minutes we was hightailing it through them prickly pear flats headed toward Crystal City. In two days we were in Crystal City, sitting in my mother’s kitchen.
“We got $4,700 off the train; more money than we had ever seen. I give Red half and we went down to the hotel and had us a big steak dinner.”
Along with the stories of ringing in the New Year, the Texas newspapers were ablaze with front-page accounts of the “daring train robbery.” The San Antonio Express quoted a number of first-hand accounts of the train robbery that vary from Willis’ version, particularly in how they treated the passengers when they demanded their cash and valuables.
Two Bandits Awaken and Rob Passengers on Southern Pacific Obtain $7840 And Many Valuables; Overlook $16,000
Robbers Boarded a Train near Spofford And Escaped After 18 Minutes’ Search of Passengers.
Are Headed for Mexico
Posse in Pursuit Following Three Clues In Hope of Effecting A Capture Before Robbers Cross the Rio Grande-Mexican Who Saves His Fortune Reimburses Those Robbed.
… More than $7,840 and a number of watches, jewels, guns and other valuables were taken and $16,000 in gold was overlooked when masked men robbed the two rear sleepers of the Sunset Central Express train between Cline and Spofford about 2:30 o’clock yesterday morning. The robbery required eighteen minutes, during which time the bandits took the belongings of 14 passengers in the San Antonio sleeper at the rear of the train, and using W. F. Kendall, brakeman as a shield continued part way through another Pullman as the train neared Spofford, when the bandits retreated to the rear Pullman, pulled the bell cord and escaped.
Although posses organized by Ranger Phelps and R. C. Watkins, division superintendent of the Sunset Central of this city, one of the victims, were organized at Spofford and Del Rio immediately after the robbery, no trace of the robbers has been found.
Two men discovered in a tool house on the Eagle Pass branch of the road were arrested and released. As the distance to the border is only about 30 miles by rail and about 33 miles by direct route, it is believed that the men are making an effort to reach the boundary line and cross into Mexico.
Jose Martinez, a wealthy mine owner of Durango, Mexico was overlooked by the bandits and remained the happy possessor of about $16,000 in cash and several hundred dollars’ worth of jewelry. Martinez and his wife and daughter, occupied the drawing room in the front end of the last sleeper. They knew nothing of the presence of the bandits until aroused by the Negro porter, John Dunmore, who told him robbers were going through the train and that they had better hide their money and valuables.
The warning was heeded and the trio waited almost breathless for the appearance of the masked pair to search their compartment. Minutes that seemed like hours passed and finally Martinez returned to stick his head out into the car and learned that the bandits had completed their mission.
Whether due to their unfamiliarity of Pullman cars or to their haste, the drawing room was slighted in the holdup game, as were those occupying upper berths. Two men in the rear sleeper occupying upper berths were not disturbed by the bandits and one never knew anything about the occurrences until later aroused by the victims when inquiring about his loss.
He made an inventory and found his purse containing $200, his gold watch and other valuables had not been molested and were under his pillow where he had put them up on retiring.
Overjoyed with having escaped the robbers, Martinez summoned the porter who had warned him and his family of the danger and handed him a roll of bills as a reward.
Learning of the plight of some of the passengers who had been relieved of every cent they had and most of them of everything else of value, Martinez decided to share his good luck and wealth with his fellow travelers. To each he gave money in sums ranging from $25-$100 in proportion to their losses and other circumstances as he learned by personal investigations.
The newspaper article went on to detail how Willis and Red roughed up the passengers to get them to hand over their valuables. Contrary to Willis’ self-described chivalry toward women, the article dispelled any doubts he was more than willing to accost women as well as men when it came to demanding all of their valuables.
… The bandits were described by passengers as brutes and were extremely rough at times in the handling of their victims. While several passengers were struck by the butts of guns in the hands of the robbers and more or less seriously wounded, not a shot was fired. At least four persons required medical attention after the bandits had taken their departure, and one woman whose name could not be learned, suffered an ugly gash in the head, which required 11 stitches to close. Exasperated at the thoughts of parting with her valuables, she first pleaded with the bandits without avail, and then she resisted their attempts to relieve her of her money and jewelry, when one of them drew his gun back and struck her across the head, inflicting an ugly gash and severe bruises.
One woman traveling with her four-month-old baby escaped brutal treatment and managed to save $185, which she had secreted under her bed. Occupying a lower birth in the rear car, she became hysterical when awakened and, looking out saw the masked bandits demanding money from the passengers. Time was valuable to the robbers and losing patience in their efforts to calm her, one of the men called out:
“Oh, let her go: she’s nothing but a baby,” and the pair moved to the next birth with orders to the brakeman to hurry and rouse the passengers.
One man who appeared slow in getting his money and time piece together was given a hard jab with the dangerous end of a gun and he dropped his money in this aisle of the car. Another rap from the gun and he was made to jump out of his birth and gather up the money and handed to the brakeman, who quickly passed it to the robbers.
One man who was a sound sleeper came within an ace of waking up in eternity when he failed to respond quickly to the shaking given him by the brakeman.
The robbers were not inclined to tarry and when the sleeper did not come across they were about to strike him a deadly blow, but the brakeman succeeded in rousing the sleeper and impressing upon him the seriousness of the situation just in time to save him from a beating.
One woman fainted and was quickly relieved of her money, jewelry, and purse containing her railroad ticket before she was revived.
This instance seems to awaken a strain of humor in the makeup of one of the holdup man, for he remarked, “If we could only put them all to sleep as easy-this would be the life.”
Apparently, some of the passengers were more than willing to exaggerate or totally fabricate their recollections of the robbery to reporters covering the holdup. In one case, a passenger identified himself as being the brother of the past president of Mexico.
… One of the first stories of the holdup obtained from an eyewitness came from Walter Grimmer, an employee of the electric light plant at Del Rio. Mr. Grimmer was a passenger out of San Antonio. He was riding in the day coach and declares emphatically that the two robbers boarded the train at San Antonio and sat almost directly across the aisle from him.
Mr. Grimmer says he was attracted to them almost as soon as the train left San Antonio by their suspicious actions and unusually tough appearance. He says a Ranger occupied a seat directly in front of him and that the men evidently recognize the officer and appeared to avoid his eyes whenever he looked in their direction.
According to Mr. Grimmer the two men waited until practically everyone in the day coach was asleep, when they left their seats and walked through the coach. Mr. Grimmer says he was awake at the time, watched the men walk through the day coach and saw them cross the platform and enter the first Pullman. He says he got a good look at the robbers and would easily be able to identify them. One he described as a man of exceptionally heavy build.
He says after going through the Pullmans the men signaled the train to stop and jumped to the ground on the moonlight side of the train. The aroused passengers saw them plainly as they ran. Both men are said to be Americans.
Benjamin Madero, brother of the late President of Mexico, is believed to have been one of the passengers in the upper berths who escaped attention. He arrived at the Sunset Station too late to get a lower birth and was consigned to the upper number five. Madero is supposed to have saved his belongings, although all of the others and excepting the passenger in the remaining upper, and the Martinez family in the drawing room, were robbed.
George Miller, a cattleman from Marathon was one of the passengers in a lower birth, and was robbed of his valuables. It is supposed that several hundred dollars were found in his possession.
Mr. and Mrs. L. T. Wood of 217 San Pedro Ave. lost their money and valuables when the brakeman awoke them and told them that the car was being robbed and to turn over everything they had.
Superintendent Watkins, who was asleep in a lower birth about the middle of the train, was one of the first to be robbed. He was relieved of $25 and pass books. Sam Scammahorn, a yard master at the Sunset Station, lost his revolver, watch and the pocketbook.
F. H. Bednarak, chief dispatcher lost his watch and some money. The three railroad men were on their way to a point on the Eagle Pass branch to hunt big game, but they joined the posse on the trail of the bandits.
C. D. Woodward, the Pullman car conductor in charge of the rear sleeper in the train, was not overlooked and the robbers relieved him of $156 including his own and the company’s money.
Following this article that gave a vivid account of the pistol-whipping some of the passengers experienced during the hold-up, the San Antonio Light ran this front-page reward notice on January 2.
The G. H. & S. A. Ry. Co. offers $500 reward for the arrest and conviction of the two men who robbed the passengers on train No. 9 on the night of Dec. 29, 1914 between Cline and Spofford, Texas, by order of Superintendent R. C. WATKINS
Apparently, the reward offer worked; the January 21 edition of the same newspaper ran a bold front-page headline.
Two Men Are Arrested As Train Bandits
Sheriff Johnson of Uvalde Is In San Antonio With
The article went on to describe the arrest of two men who were working on a ranch near Uvalde. One was a recently released convict who had served time for burglary. Working on a tip, the Uvalde County sheriff sent two men to the ranch to surreptitiously identify the two men:
… Superintendent Watkins and W. C. Cox, both whom had been passengers on the train, went to Uvalde and, so as not to excite suspicion, went on a bird hunt to a ranch eighteen miles west of Uvalde, where the two suspects were working. Both declared there could be no doubt as to one of the men and they believed they could identify the other as well.
As it turned out the reward was never paid to the informant; the case fell apart when one of the eyewitnesses, a woman, could not positively identify the redheaded man. The law stayed on the case for a few more months and then slowly let it fade away.
Willis was never arrested for the hold-up. For some reason he concentrated on bank jobs until 1921 when he and his gang reeled off three train heists during that year. Then in 1924, the Newton Gang hit the grand slam, ripping off over $3 million from an express mail train near Rondout, Illinois.