So, roughly 101 years ago Big Ben Kilpatrick was free and clear and headed for his brother Boone Kilpatrick's ranch in Sheffield, Texas. It was mid September, 1911. It appears that Ben had made friends with a fellow named Ole Hobek in the Atlanta Penitentiary and the two men were in regular contact after both were released around the same time. Below we get some insight into what Ben, a friend or two, his brother Felix, his brother-in-law Dan Sheffield, and Ole had going almost immediately after Ben got free of the murder charge.
According to "thetalltexan.net",
"Circumstantial evidence indicates Ben and his entourage (Brother Felix Kilpatrick, Brother in-law Dan Sheffield and others) and Ole Hobek robbed a train just outside of Memphis, Tennessee on November 1, 1911 and again on February 6, 1912. Ben’s partner Ole Hobek worked at the L.B. Price Mercantile Company at Memphis, Tennessee from July 1911 through February 5th, 1912, quitting just one day prior to the second train robbery. Ole had made an appearance in San Angelo in the Spring of 1911, anticipating Ben’s release. The robbery of the GH & SA train was likely to have occurred in the spring of 1911 but was delayed by Ben’s failure to secure probation, parole or pardon from his Federal Prison sentence.
By mid February 1912 the gang was back in Pecos and Terrell County Texas finalizing plans for the robbery. Several in-law's of Ben’s would witness his presence and actions at Brother Boone’s ranch just outside of Sheffield, Texas. They stated Ben spent a lot of time writing letters and would go on long horseback rides. Likely, Ben was trying to secure additional help and was scouting escape routes and learning the terrain. Several witnesses were treated to impressive displays of Ben’s marksmanship watching him shoot the heads off of chickens and apples off of sticks."
Heads off chickens? Remember the opening scene in "Pat Garrett and Billy the Kid"? The directors cut opens with Billy and friends shooting heads off live chickens. Ben now planned to rob the Galveston, Harrisburg and San Antonio Railroad on March 12, 1912 between Dryden and Sanderson, Texas. The location made a lot of sense with the exception of the site of the robbery being so closed to home. . .
Again from "thetalltexan.net:
"On Saturday March 10, 1912 Ben, Ole and what was described as two young white men and two Mexicans would leave Sheffield by horseback. On the evening of March 11, 1912 Ben and Ole would be spotted at the depot at Sanderson. Shortly before midnight on March 12, 1912, the train pulled into Dryden and was boarded by Ben and Ole. They first asserted there were no soldiers on board. They then cover Engineer D.E. Grosh with pistols and order him to stop at the first iron bridge west of Eldridge. The location is about half way between Sanderson and Dryden."
The stage is now set for aging outlaws to try one last train robbery.
"While there are conflicting accounts as to which robber was killed by a rifle shot and which was dispatched with an ice mallet the basic facts concerning the robbery are clear. On March 12, 1912 at 8:02 p.m. GH&SA RR (Galveston, Harrisburg, and San Antonio Rail Road) Train No. 9, engine No. 709 left Del Rio, Texas with engineer D. E. Grosh at the throttle. It was making a scheduled passenger, baggage, and mail run to its final destination of El Paso. Shortly before midnight, it stopped in Dryden, Texas to take on water for steam generation. As the train was preparing to pull out, the two robbers (Ben Kilpatrick and Ole Hobek) climbed aboard the engine and ordered Grosh to proceed to the first iron bridge east of Baxter’s Curve. The official time of the robbery is listed at 12:05 a.m. on March 13, 1912 by the railroad.
The events that followed after the train stopped at the iron bridge are best related by using the official statement taken from David A. Trousdale on March 15, 1912 at the Wells Fargo and Company’s office in San Antonio, Texas. Mr. Trousdale was the express manager Wells Fargo assigned to Train No. 9 and as such was responsible for overseeing the mail, baggage, and any gold or other valuables that the combination mail and baggage cars were carrying."
David Trousdale, the hero's full account:
“The first I knew of being held up was when the train came to a stop at Baxter’s Curve. I did not go to the door, and did not know there was any trouble until the train porter, or the engineer called me and asked me to come to the door. I opened the door, and when I looked out, there was a man with a mask on, standing there pointing a rifle at me. The train porter told me that I was wanted out there; that there were robbers and I had better come out. I stood there for a few seconds and the robber told me to ‘fall out’ with my hands up. When I got out of the car, he walked up to me and searched me for arms; and then made me stand back with the train crew. He made the conductor and the train porter uncouple the baggage cars from the coaches and move away about 10 to 12 feet….He searched the helper, and gave the conductor and porter instructions to go back and stay with the coaches; the mail clerk, the helper, and I to go on the engine. One of the robbers rode on one side of the engine in the gang way and one on the other side. They carried us something like a mile from the place they held us up.
“The robber going by the name of ‘Partner’ stayed with the engineer and fireman; and the other one going by the name of ‘Frank’ had the mail clerk, the helper, and myself line up by the side of the engine tank and marched us back to the baggage car and made us get up into the car, holding our hands up. He then carried us over to the safe and had me open it. I only had sever money waybills in the safe, and out of the seven, I told hem that there were only two of any value to him. I got him to take two packages one valued at $2.00 and the other $37.00. After he had looked over the car, he said he would go through and see what Uncle Sam had and he carried the three of us back to the mail car. He cut one mail pouch open and put all of the loose registers in it; and threw it out with four others, filled with registers; and told me that he would take me across the river (meaning the Rio Grande) with him.
“I thought if there was any chance for me to get the advantage on him, it would be by taking him back through my car where I could find some means of turning the table on him. We passed through the combination car and I opened two or three packages of express; and he took his knife and cut one telescope grip open. He took out a Mexican hat and said there was nothing in the baggage that he wanted. The robber, helper Reagan, and I went on into the through car. I told him that I was not getting fighting wages and did not care how much he took out. In this way I gained his confidence and he quit treating me as roughly as he had been. Before this, he would jab me with his rifle and command me around in a boisterous manner. When we passed by a stack of oysters, I had an empty packer standing in about the center of the car, and the robber and I had to pass between the oysters and the packer, and this crowded me close to the oysters; and as we passed, I picked up the ice-maul which was lying on them. I placed it behind my overcoat so that he could not see it and got him away from the door and showed him a package which was going to Sanderson, and told him that the package was worth more than all he had gotten, I thought. He rested his rifle against his leg and started to pick up the package in his right hand. While he was in this position, I saw my chance, and so the first blow I struck him was at the base of the skull, adjoining his head from his neck. Then I struck him two more blows in the top of the head after he had fallen, and knocked his brains out the third blow.
“I took two .45 caliber Colt revolvers and a 401 Model Winchester off this man. I gave the mail clerk and the helper each a revolver and I kept the rifle. I sent the mail clerk and helper to the rear end of the car. I turned the lights out and then joined them and the only way we could see was from the lights in the combination car. I waited something like two hours for the second man to come back. He did not show up for sometime, and I fired a shot through the top of the car, and in a few minutes, he came to the door and called the name ‘Frank’ three times; and waited about five minutes, then I saw his head sticking out from behind a trunk forty feet from me. The first time he put his head out I did not get a chance to shoot, but the second time he was looking toward the rear of the car. I fired one shot – the bullet striking him about an inch and a half above the left eye, passing through his head and started going through the end of the car. After waiting about an hour, we pulled the air and the engineer backed the engine and baggage cars back to the coaches. The fireman came back to the coaches and called me. I told him to get the conductor and some of the passengers before I could open the car, that I had killed two men. In a few minutes he came back with the conductor, porter, and fifteen or twenty passengers. When I found that there was no one out there to harm me, I opened the door and admitted the train crew.
“After getting the train coupled up, we moved up to where the US mail had been unloaded and found everything there as it had been unloaded, and I got the two sealed packages that had been taken out of my safe. I transferred all of my money run to Helper Reagan and went as far as Sanderson and unloaded the dead bodies with the six guns taken from them. I then went before the Grand Jury and the coroner’s court and was released.
“In conclusion, I will state that while on the way to Sanderson, I removed six sticks of dynamite and a box of dynamite caps and an ‘Infernal Machine’ from the man called ‘Partner’. The man called ‘Frank’ had a pint of Nitro-Glycerine in his side pocket.”
For his actions in stopping the attempted robbery and preventing potential harm to the passengers, Mr. Trousdale was awarded $51 collected on the spot by the passengers. The Wells Fargo Co. awarded him $1,000, the Federal government gave him $1,000 and the Southern Pacific Lines added another $500. In addition Wells Fargo presented him with a gold watch engraved with: “In recognition of the courage and fidelity displayed in an attempted train robbery near Dryden, Texas, March 13, 1912, Wells Fargo and Co.”
To go with the gold watch; the train passengers gave him a gold watch fob inlaid with a diamond inside the star of Texas. The inscription reads: “Presented by passengers, west-bound Sunset Express, for bravery displayed March 13, 1912, near Dryden, Texas.”
The robbers, after being posed for a picture at the Sanderson Train Depot, were buried together in the Cedar Grove Cemetery in Sanderson, Texas. Their joint grave has a marker erected by the Terrell County Historical Commission and is still a spot of interest to tourists and also draws those who are students of the Wild West era."
Ben Kilpatrick and Ole Hobeck:
Sanderson Train Station:
I don't recall it looking like that though, of course I didn't see the Railway Station.
I hunt them with a trench gun as it's my only shotty. Kind of comical to walk into the woods with a Mossberg 590, squirrel hunting but I have only missed one shot this year. . . just gotta let 'em get a bit closer 
Must have been nice when men were men and women were glad of it.
