During his 32 years in crime Henry Starr robbed more banks than both the James-Younger Gang and the Doolin-Dalton Gang put together. He started robbing banks on horseback in 1893 and ended up robbing his last in a car in 1921. The Cherokee Badman netted over $60,000 from more than 21 bank robberies.
Henry Starr was born near Fort Gibson in Indian Territory on December 2, 1873 to George “Hop” Starr, a half-breed Cherokee, and Mary Scot Starr, a woman of Irish decent and one-quarter Cherokee. Mary came from an educated and respectable family, but the Starr side of the family was rife with outlaws. Henry’s grandfather was Tom Starr, an outlaw in his own right. Henry would later say that his grandfather “was known far and wide as the Devil’s own. In all matters where law and order was on one side, Tom Starr was on the other.”
His uncle was the notorious Sam Starr who was married to Belle Starr, the “Outlaw Queen.” Belle Starr was widely known for her relationship with the notorious Younger Gang and her criminal escapades through Oklahoma. Henry though, reportedly was not fond of Belle, finding her to be crude and reprehensible, quickly informing anyone who commented on the relationship, that she was his aunt by marriage only.
During the time of Starr’s youth, the northeastern corner of Indian Territory was rugged and untamed, often referred to as the “Land of the Six-Gun” and the “Robbers’ Roost.” The rough terrain of the area provided a number of natural hideouts for thieves, murderers, and other outlaws seeking refuge from the law.
In 1886, Henry’s father died leaving Mary to care for three children and the family farm. However, within just a few months she remarried a man by the name of C.N. Walker, who Henry hated. Starr felt that Walker was inferior because his veins contained no Indian blood. Walker was also abusive and he and Henry had immediate problems. Within just a few short months of his mother’s remarriage Henry left home.
By the age of sixteen, while Henry was working on a ranch near Nowata, in Indian Territory, he had his first run-in with the law. As Henry was driving a wagon to town two deputy marshals caught him with whiskey and arrested him for “introducing spirits into territory.” Though he plead guilty to the offense, he maintained that he was innocent, having borrowed the wagon without knowing that the whiskey was in it.
Starr returned to Nowata and continued to work as a cowboy, but it wasn’t long before he had another run-in with the law. In December 1891, he was arrested for stealing a horse, again he denied the charge, but was locked up at Fort Smith, Arkansas anyway. His cousin paid his bail and Starr hit the road, with a warrant for his arrest hanging over his head. After jumping bail, Henry had made a conscious choice to live on the wrong side of the law. The warrant for Starr’s arrest was given to Deputy Marshals Henry C. Dickey and Floyd Wilson who were quickly on Henry’s tail.
Joining up with Ed Newcome and Jesse Jackson, the gang began to rob stores and railroad depots. Hitting their first railroad depot right where he lived, Starr and his gang relieved the Nowata Depot of $1,700 in July 1892. In November 1892, they hit Shufeldts Store at Lenapah, Indian Territory taking $300 and in the same month robbed Carter’s Store in Sequoyah, Indian Territory making off with $180.
By December 1892, Deputy Marshals Dickey and Wilson were very close to finding Henry. Following his trail, the two marshals arrived at Arthur Dodge’s “XU Ranch,” eight miles from Nowata, where it was rumored that the Starr Gang might be meeting. Upon arriving at the ranch, the marshals questioned Arthur Dodge who denied knowing Starr personally, but stated that he had seen the bandit ride by the ranch several times. The lawmen searched the surrounding countryside until late into the night, but found no trace of Starr or his gang. However, the next day, on December 13, 1892, the two lawmen were having dinner at the Dodge Ranch when Mr. Dodge informed them that he had seen Henry that day while working on the ranch.
Wilson rushed to the barn, mounted an already saddled horse, and sped off in pursuit of Henry. Dickey’s mount was unsaddled so he was several minutes behind Wilson. Before long, Wilson found Henry in an opening on Wolf Creek. Spotting each other at almost the same moment, Starr dropped from his saddle while Wilson remained mounted about thirty yards away. Wilson ordered Henry to surrender, but Henry just “walked away.” Wilson then stated that he had a warrant for his arrest and rode closer to Henry, stopping some 25 or 30 feet from him. Wilson then dismounted, raised his rifle, and fired a warning shot over Henry’s head.
With that first shot, Starr returned fire and a gunfight ensued. Wilson was hit and fell to the ground, badly wounded. When Wilson tried to load a fresh cartridge into his rifle, the weapon jammed and he threw it aside, reaching for his pistol. Starr fired two more shots and Wilson sank to the ground, too weak to defend himself.
Then, calmly walking over to Wilson, Starr fired one more round into his heart. At the sounds of the shots, the frightened horses rode away, but Henry was able to catch Wilson’s horse and took off. By the time Marshal Dickey arrived, the whole affair was over and Starr was long gone.
Now, Henry was wanted for murder and the law doubled their efforts to find him. On January 20, 1893, Starr was nearly caught when Indian Police picked up his trail near Bartlesville, I.T. (Indian Territory). A gun battle broke out but Starr was able to escape. Teaming up with a man by the name of Frank Cheney, Starr and Cheney robbed the MKT railroad depot of $180 and Haden’s Store of $390 in Choteau, I.T. In February, they hit the railroad depot and general store in Inola, I.T. making off with $220.
Seemingly not bothered by the law hot on their trail, Starr and Cheney grew bolder and robbed their first bank in Caney, Kansas on March 28, 1893, relieving the Caney Valley Bank of $4,900. The two men entered the Caney National Bank with their revolvers drawn. Cheney entered the vault carrying an old two-bushel sack and emerged from the vault with the bag filled with currency. Starr and his partner locked the bank’s customers and employees in a back room and exited the bank. One Kansas newspaper said of the robbery that it was “one of the boldest and most daring robberies known to border history.”
Just a little more than a month later, they robbed their first passenger train at Pryor Creek, I.T., making off with $6,000.
Not to be stopped, Starr chose the People’s Bank of Bentonville, Arkansas for their next robbery. On June 5, 1893, Starr and four partners rode into the small, northwest Arkansas town. However, by 1893, Starr was an infamous man and people recognized him as soon as he entered the town.