Near daybreak the morning of Wednesday, February 27, 1895, Deputy Marshal James Nakedhead was a member of a group of deputy marshals and Texas Rangers that surrounded Ben Hughes’ house near Brush Hill, about ten miles southwest of present-day Checotah, in hopes of arresting the Hughes gang, suspected of a Texas train robbery occurring October 19, 1894 near Gordon, Texas.
According to contemporary newspaper reports filed in the Cherokee Advocate (Tahlequah) that were distributed as far as the New York Times, %100,000 was taken in the brazen daytime robbery of the Texas Pacific Express in mid- January. Although that quoted amount was never confirmed by the railroad the heist is still considered one of the largest amounts seized by bandits during the pre-statehood era f Oklahoma.
Evidence showed that Sam Baker along with the Hughes brothers Ben and Jim committed the train robbery. Others suspected in the robbery were Shirley Smith and Judd South, who also went by Judd Southern and Judd Silvers.
Marshals had received information that the Hughes gang had moved their operations to he Indian Territory and had hatched a scheme to attempt another robbery, this time against the Missouri, Kansas and Texas Railroad. The US Deputy Mashals and the Rangers trailed the gang all night, tracking them to the Hughes homestead southwest of Checotah.
On the morning of the incident, the gang’s dogs alerted the outlaws to the officers’ approach , and they began firing on the posse. During the gun battle that followed Ben Hughes ran from the house and into the nearby brush. Judd South was next to come out running and firing at the officers.
As Deputy Marshal Nakedhead rose to fire at the running Judd South, Ben Hughes fired from hiding at Nakedhead striking him in the head and killing him instantly. Judd South escaped into the brush.
Outlaw Ben Hughes was then wounded in the arm by the officers. Ben Hughes wife ran from the house with more ammunition for her husband and was arrested. When Ben Hughes saw his wife was arrested, he surrendered. Judd South was soon located and arrested.
Deputy Marshal James Nakedhead, a Cherokee, was survived by his wife and several children and is buried in Tahlequah Cemetery, Tahlequah, Cherokee County, Oklahoma.
Ben Hughes and Judd South were eventually taken to Dallas, Texas and placed in jail to await their trial on the train robbery.
On May 18th Jim Hughes was arrested by Texas Ranger Captain Bill McDonald and was also taken to Dallas and placed in jail. Jim Hughes’ alibi the day of the train robbery checked out to be true and he was released.
It is unknown what the outcome of the train robbery case was, but Ben Hughes and Judd South later stood trial in Fort Smith for the murder of Deputy Marshal James Nakedhead. The Hughes brothers pleaded innocent citing self-defense.
When it was brought out that the Texas officers did not have an arrest warrant for Ben Hughes or Judd South at the time of the shootout both men were acquitted and freed.
Eight years later in early 1903, Ben Hughes and his brother, Jim, were tried in Fort Smith for the brutal October 20, 1902, murder of another Deputy U.S. Marshal, Lute Houston, by members of the Bert Casey gang and again the Hughes brothers were acquitted.
