Last Updated: 2 months Henry Starr, Cherokee, (1873–1921) was the last in a long line of Starr family criminals. Twice sentenced by Judge Isaac Parker to hang for murder, he managed to escape the noose due to technicalities and went on to form a notorious gang that terrorized and robbed throughout northwest Arkansas and Colorado around the start of the 20th century.
He started robbing banks on horseback in 1893 and ended up robbing his last bank in a car in 1921. He was the first to rob a bank using a car to get away. The Cherokee Badman netted over $60,000 from more than 21 bank robberies during his career as an outlaw. During his 32 years in crime Henry Starr robbed more banks than both the James-Younger Gang and the Doolin-Dalton Gang put together.
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, and the area was often featured in old western movies.
Sam Starr hated his step-father
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 he wasn’t Indian. 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 the 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.
Henry Starr hits the outlaw trail after being arrested for horse thievery
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, which he again denied, 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 trail.
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.
Starr commits his first murder
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 ran 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, Indian Territory. A gun battle broke out but Starr was able to escape.
Sam Starr teamed up with an outlaw named Frank Cheney
Next 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, Indian Territory. In February, they hit the railroad depot and general store in Inola, Indian Territory, making off with $220.
Starr and Cheney grew bolder and robbed their first bank in Caney, Kansas on March 28, 1893
They relieved 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, Indian Territory, 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.
By the time Starr and Kid Wilson entered the bank, an alarm was quickly spreading that the bank was being robbed. Gunfire erupted outside the bank and Starr and Wilson left the bank while the robbery was still in progress.
Starr and Wilson raced for their horses, and the gang of bandits fled from Bentonville with the posse right behind them. When they reached safety, they counted their take and were disappointed to find only $11,000, which had to be split between five men.
Following the Bentonville robbery, Henry Starr and his gang were constantly pursued by the law.
With a $5,000 reward offered for Starr, the gang decided to split up for a time.
Henry, Kid Wilson and a lady friend boarded a train at Emporia, Kansas, heading to California. Enroute, they stopped at Colorado Springs to replenish the lady’s wardrobe and do some sight-seeing.
On July 3, 1893, they checked into the Spaulding House. Henry registered as Frank Johnson and the Kid registered as John Wilson, both from Joplin, Missouri. However, officers discovered they were there and Starr was arrested in the restaurant. Later they picked up Wilson in Colorado City. Returning to the Spaulding House, they woke up the woman, who was registered as Mrs. Jackson, but who admitted to being Starr’s wife of six months. In a search of the room, the lawmen found $1,460 in greenbacks and about $500 in gold.
Starr and Wilson were returned to Fort Smith, Arkansas on July 13, 1893 to stand trial.
Starr was charged with thirteen counts of highway robbery, and one count of murder. The trial revolved around the murder charge and Starr was found guilty by Judge Isaac Parker and sentenced to hang.
Henry’s lawyers appealed the case and the U.S Supreme Court overturned Parker’s decision and granted Starr a new trial. He was found guilty at the second trial and again sentenced to hang, but again his lawyers were able to appeal and get Henry yet another trial.
It was during his stay in jail at Fort Smith, Arkansas awaiting trial, that fellow prisoner, Crawford Goldsby, alias Cherokee Bill attempted a jailbreak with a gun smuggled to him by a trustee. There was a gun battle between Bill and the prison guards, in which one of the guards was killed.
However, the guards were unable to disarm Bill and it was standoff. Henry and Bill were old acquaintances and Henry offered to disarm Bill if the guards would in turn promise not to kill Cherokee Bill afterwards. The promise was made and Henry entered the cell telling his friend that he had no chance of escape. Cherokee Bill gave up his revolver and Starr turned it over to the guards. This incident helped Henry to later acquire his freedom.
In 1901, Henry, with help from his family and the Cherokee Tribal Government, applied for a pardon. President Roosevelt so admired the man for his courage in the Cherokee Bill incident that he reduced his sentence and Henry was released from prison on January 16, 1903.
After his release from prison, Henry returned to Tulsa, Indian Territory and worked in his mother’s restaurant. It was here that he met and married his second wife, Miss Ollie Griffin in September 1903.
In 1904 Theodore Roosevelt Starr was born.
After the birth of his son, Henry led an honest life for a while until officials in Arkansas learned of Starr’s release. They immediately began seeking his extradition for the 1893 Bentonville robbery. Henry took to the safety of the Osage Hills, quickly falling in with his old partners. Later, he would write, “I preferred a quiet and unostentatious interment in a respectable cemetery rather than a life on the Arkansas convict farm.”
On March 13, 1908, Henry and his gang crossed the Kansas border and robbed the bank at Tyro, Kansas. Though pursued by a posse of over twenty men, Starr and his gang were able to get away. Henry then headed west, along with Kid Wilson.
When the pair hit Amity, Colorado in May, they robbed the local bank of $1,100. Soon after the Amity robbery, Kid Wilson and Starr separated.
History fails to tell us what ever became of Kid Wilson but Starr spent the summer and fall of 1908 hiding in New Mexico and Arizona. When he wrote to a friend back in Tulsa, the supposed friend betrayed him, and on May 13, 1908, Starr was once again placed under arrest to be extradited to Colorado.
At the third trial, Henry plead guilty to manslaughter and was sentenced to a total of 15 years — 3 for manslaughter, 7 years for 7 counts of robbery, and 5 years for 1 count of train robbery. On January 15, 1898, Henry Starr was transported to the federal prison at Columbus, Ohio.
On November 24, 1908, Henry plead guilty to the Amity robbing and was sentenced to 7 – 25 years in the Canon City, Colorado Prison. During his imprisonment, Henry worked as a trustee, studied law in the prison library and wrote his autobiography entitled Thrilling Events: Life of Henry Starr.
Starr returns to Oklahoma and is wanted Dead or Alive
On September 24, 1913, he was paroled by the governor and was free again, with the stipulation that he never leave the state of Colorado. Starr did not keep his promise, instead returning to Oklahoma, and his old ways.
Between September 8, 1914, and January 13, 1915, fourteen different bank robberies were attributed to Henry Starr. All were daylight robberies, carried off quickly and efficiently, at two-week intervals. This was the worst streak of robberies the people of Oklahoma had ever witnessed, and in response to the cries of the citizens, the state legislature passed the “Bank Robber Bill,” which appropriated $15,000 for the capture of bank robbers and placed a $1,000 bounty on Starr’s head. The reward was payable “Dead or Alive.”
Convinced that Starr was hiding in the Osage Hills, the law was relentlessly tracking all of his old hideouts. However, the clever Henry was living in the heart of Tulsa, at 1534 East Second Street, just two blocks from the Tulsa County Sheriff and four blocks from the mayor of Tulsa.
Then on March 27, 1915 Henry and six other men rode into the town of Stroud, Oklahoma. Starr’s plan was to rob two banks at the same time, much as the Dalton Gang had unsuccessfully tried to do in Coffeyville, Kansas in 1892.
The Stroud, Oklahoma robbery would prove disastrous for Henry Starr.
Proceeding to rob the Stroud National Bank and the First National Bank, word of the holdup spread quickly and the citizens took up arms against the bandits. Henry and another outlaw named Lewis Estes were wounded and captured in the gun battle. The rest of the gang escaped with $5815, successfully pulling off the double daylight bank robbery.
After Starr recovered from his wound, he stood trial and entered a plea of guilty to the Stroud Robbery on August 2, 1915. Sentenced to 25 years, he was transferred to the Oklahoma State Penitentiary at McAlester, Oklahoma.
While in prison at McAlester, Starr began speaking of the foolishness of a life of crime, urging young people to stay honest and earn their money in a legal manner.
“I’m 45 years old now,” Starr told a reporter from the Oklahoma World, “And 17 of my 45 years have been spent ‘inside.’ Isn’t that enough to tell any boy that there’s nothing to the kind of life I have led?” The good words had the proper effect. Starr was paroled in on March 15, 1919.
The silent movie “A Debtor to the Law” is a hit
For two years, the famous bandit stayed true to his word and lived an honest life. He even encouraged others to do so by starring in “A Debtor to the Law”, a film, which depicted the Stroud, Oklahoma, bank robbery and the senselessness of crime.
Henry produced and starred in the silent movie, which was an immediate and huge success. He went on to star in a couple of other movies, and received an offer from Hollywood to do a movie out there. He turned it down because he was afraid that if he went to Hollywood the authorities in Arkansas would try to extradite him for his part in the Bentonville robbery. It was during his time in the movies that Henry met and married his third wife, Hulda Starr from Salisaw, Oklahoma. They were married on February 22, 1920 and moved to Claremore, Oklahoma.
But it just wasn’t in Starr to live the life an honest man for very long. On Friday morning, February 18, 1921, Henry and three companions drove into Harrison, Arkansas. They entered the People’s State Bank and robbed it of $6000.
During the robbery, Henry was shot in the back by the former president of the bank, and his partners fled, leaving him to face the music alone. He was carried to the jail where doctors removed the bullet.
Obviously proud of his record, he boasted to the doctors on Monday, February 21, 1921 “I’ve robbed more banks than any man in America.” The next morning he died from his wound with his wife, Hulda, his mother and his 17-year-old son at his side.
Henry died as he had lived, in a violent manner, but true to the code of the outlaws
He never revealed a single partner in any crime. He never shot anyone in the commission of a crime. He had succeeded where others had failed by robbing two banks at once, and by robbing more banks than anyone else.
During his 32 years in crime, he claimed to have 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. Allegedly, he robbed 21 banks during his outlaw career, making off with nearly $60,000.00, a fortune in his time.
The loot from Starr’s earlier crimes was, by his own words, hidden “..near the border in a place nobody could find it in a million years.” Many researchers believe that this cache is hidden somewhere along the Cimarron River in Stevens County, Kansas.