Henry Starr, a name synonymous with audacious bank robberies and a life lived on the fringes of the law, carved a unique and controversial place for himself in the annals of the American West. Born into a family steeped in both Cherokee heritage and outlawry, Henry Starr (1873-1921) ultimately eclipsed the notoriety of even the most infamous gangs of his era. While the James-Younger Gang and the Doolin-Dalton Gang have secured their legendary status through dramatic exploits, Henry Starr’s sheer volume of successful bank robberies dwarfs their combined efforts, marking him as a particularly prolific and audacious figure in the history of American crime.
This article delves into the life and times of Henry Starr, exploring his origins, his criminal career, and the factors that contributed to his extraordinary success and enduring legend.
A Lineage of Outlaws
Born on December 2, 1873, near Fort Gibson in Indian Territory (present-day Oklahoma), Henry Starr’s parentage was a blend of cultures and destinies. His father, George "Hop" Starr, was a half-breed Cherokee, while his mother, Mary Scot Starr, was of Irish descent with one-quarter Cherokee blood. While Mary hailed from a family of education and respectability, the Starr side was deeply entwined with outlawry.
Henry’s grandfather, Tom Starr, was himself a notorious figure, described by Henry as "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." This familial legacy of defiance and disregard for the law undoubtedly shaped Henry’s worldview and path in life.
Adding further to the family’s outlaw mystique was Henry’s uncle, Sam Starr, famously married to Belle Starr, the "Outlaw Queen." Belle was renowned for her connections to the Younger Gang and her own criminal escapades in Oklahoma. However, Henry reportedly held a less-than-favorable view of Belle, finding her crude and quickly dismissing any perceived association beyond her being his aunt by marriage.
The environment in which Henry grew up further contributed to his eventual life of crime. The northeastern corner of Indian Territory during his youth was a rugged, lawless region, often called the "Land of the Six-Gun" and the "Robbers’ Roost." The terrain was unforgiving, providing numerous natural hideouts for outlaws seeking refuge from the authorities. This wild and untamed atmosphere fostered a culture where crime thrived and the allure of easy money and freedom from societal constraints proved irresistible to some.
Early Encounters with the Law
Henry’s home life took a turn for the worse in 1886 when his father died, leaving Mary to care for her three children and the family farm. Within months, she remarried a man named C.N. Walker, whom Henry despised. Starr felt that Walker was inferior because he wasn’t Indian. Walker was also abusive, leading to immediate friction between him and Henry. Within a few short months of his mother’s remarriage, Henry left home.
By the age of sixteen, while working on a ranch near Nowata in Indian Territory, Henry had his first encounter with the law. While driving a wagon to town, he was caught with whiskey by two deputy marshals and arrested for "introducing spirits into the territory." Despite pleading guilty, he maintained his innocence, claiming he had borrowed the wagon without knowing the whiskey was present.
His life as a cowboy in Nowata did not last long before he ran afoul of the law again. In December 1891, he was arrested for stealing a horse, a charge he vehemently denied. Despite his denials, he was locked up at Fort Smith, Arkansas. His cousin posted bail, and Starr, with a warrant hanging over his head, made the fateful decision to flee.
On the Outlaw Trail
Jumping bail marked a turning point in Henry’s life, solidifying his decision to embrace a life outside the law. With a warrant for his arrest issued to Deputy Marshals Henry C. Dickey and Floyd Wilson, the chase was on.
Starr joined forces with Ed Newcome and Jesse Jackson, forming a gang that began to rob stores and railroad depots. Their first target was the Nowata Depot, where they made off with $1,700 in July 1892. This was followed by robberies of Shufeldts Store at Lenapah and Carter’s Store in Sequoyah, netting them $300 and $180 respectively.
As the gang’s activities increased, Deputy Marshals Dickey and Wilson closed in. In December 1892, they arrived at Arthur Dodge’s "XU Ranch" near Nowata, rumored to be a meeting place for the Starr Gang. While Dodge denied knowing Starr personally, he admitted to seeing him ride by the ranch.
The marshals searched the area but found no trace of the gang. The following day, however, Dodge informed them he had seen Henry while working on the ranch.
A Descent into Violence
Wilson immediately pursued Henry, leading to a confrontation near Wolf Creek. Both men spotted each other simultaneously. Wilson ordered Henry to surrender, but Henry "walked away." Wilson reiterated the warrant for his arrest and rode closer, firing a warning shot.
Henry returned fire, and a gunfight ensued. Wilson was hit and fell to the ground. When he attempted to reload, his rifle jammed, forcing him to reach for his pistol. Starr fired two more shots, leaving Wilson too weak to defend himself.
Starr calmly walked over to Wilson and fired a final shot into his heart. He then caught Wilson’s horse and fled. By the time Marshal Dickey arrived, Starr was long gone.
Now wanted for murder, the law intensified its efforts to capture Starr. In January 1893, he narrowly escaped capture near Bartlesville after a gun battle with Indian Police.
Expanding Criminal Horizons
Teaming up with Frank Cheney, Starr and Cheney robbed the MKT railroad depot and Haden’s Store in Choteau, followed by the railroad depot and general store in Inola. The duo then escalated their crimes by robbing their first bank in Caney, Kansas, on March 28, 1893.
They relieved the Caney Valley Bank of $4,900. The men entered with revolvers drawn, with Cheney carrying a sack into the vault and emerging with it filled with currency. They locked the bank’s customers and employees in a back room and fled. The robbery was described by one Kansas newspaper as "one of the boldest and most daring robberies known to border history."
Just over a month later, they robbed their first passenger train at Pryor Creek, taking $6,000.
Undeterred, Starr targeted the People’s Bank of Bentonville, Arkansas, on June 5, 1893. By this time, Starr’s infamy preceded him, and he was quickly recognized upon entering the town.
As Starr and Kid Wilson entered the bank, an alarm was raised. Gunfire erupted outside, forcing Starr and Wilson to abandon the robbery in progress. They fled with their gang, pursued by a posse. They managed to escape, but their take was a disappointing $11,000, to be divided among five men.
Capture, Trial, and an Unexpected Pardon
Following the Bentonville robbery, Starr and his gang were relentlessly pursued. With a $5,000 reward offered for Starr’s capture, the gang decided to split up.
Henry, Kid Wilson, and a female companion boarded a train to California, stopping in Colorado Springs for sightseeing and to replenish the woman’s wardrobe. On July 3, 1893, they checked into the Spaulding House under false names. However, officers discovered their presence, and Starr was arrested in the restaurant, followed by Wilson in Colorado City. The woman, registered as Mrs. Jackson, admitted to being Starr’s wife of six months. A search of the room revealed $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 focused on the murder charge, and Starr was found guilty by Judge Isaac Parker and sentenced to hang.
His lawyers appealed the case, and the U.S. Supreme Court overturned Parker’s decision, granting Starr a new trial. He was found guilty again at the second trial and sentenced to hang, but his lawyers secured another appeal.
While awaiting trial at Fort Smith, Starr played a role in quelling a jailbreak attempt by fellow prisoner Crawford Goldsby, alias Cherokee Bill. Goldsby, armed with a smuggled gun, engaged in a gun battle with prison guards, resulting in the death of one guard.
Henry, an acquaintance of Goldsby, offered to disarm him if the guards promised not to kill him afterward. The promise was made, and Henry persuaded Goldsby to surrender his revolver, which Starr then handed over to the guards. This act of courage later played a role in Starr’s eventual freedom.
In 1901, with the help of his family and the Cherokee Tribal Government, Henry applied for a pardon. President Roosevelt, impressed by Starr’s courage in the Cherokee Bill incident, reduced his sentence, and Henry was released from prison on January 16, 1903.
A Brief Attempt at Reform
After his release, Henry returned to Tulsa, Indian Territory, and worked in his mother’s restaurant. He married Miss Ollie Griffin in September 1903.
After the birth of his son, Theodore Roosevelt Starr, Henry led an honest life for a while until officials in Arkansas sought his extradition for the 1893 Bentonville robbery. Henry retreated to the Osage Hills and rejoined his old partners. He later wrote, "I preferred a quiet and unostentatious interment in a respectable cemetery rather than a life on the Arkansas convict farm."
Back to the Bandit Life
On March 13, 1908, Henry and his gang robbed the bank at Tyro, Kansas. Though pursued by a posse, they escaped. Henry then headed west with Kid Wilson.
In May, they robbed the bank in Amity, Colorado, of $1,100. Soon after, Kid Wilson and Starr separated. Starr spent the summer and fall of 1908 hiding in New Mexico and Arizona. However, a supposed friend betrayed him, and on May 13, 1908, Starr was arrested again to be extradited to Colorado.
At his third trial, Henry pleaded guilty to manslaughter and was sentenced to a total of 15 years. He was transported to the federal prison at Columbus, Ohio, on January 15, 1898.
On November 24, 1908, Henry pleaded guilty to the Amity robbery 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, "Thrilling Events: Life of Henry Starr."
A Final Spree and a Violent End
On September 24, 1913, he was paroled with the stipulation that he never leave Colorado. Starr violated his parole and returned to Oklahoma.
Between September 8, 1914, and January 13, 1915, fourteen bank robberies were attributed to Henry Starr. These daylight robberies, carried out quickly and efficiently, occurred every two weeks. This crime wave prompted the state legislature to pass the "Bank Robber Bill," appropriating $15,000 for the capture of bank robbers and placing a $1,000 bounty on Starr’s head, payable "Dead or Alive."
Despite the intense manhunt, Starr was living in Tulsa, just blocks from the sheriff and mayor.
On March 27, 1915, Henry and six others rode into Stroud, Oklahoma, planning to rob two banks simultaneously, similar to the Dalton Gang’s failed attempt in Coffeyville, Kansas.
The Stroud robbery proved disastrous for Henry Starr. As they robbed the Stroud National Bank and the First National Bank, word spread quickly, and the citizens took up arms. Henry and another outlaw, Lewis Estes, were wounded and captured. The rest of the gang escaped with $5815, successfully completing the double bank robbery.
After recovering from his wound, Starr pleaded guilty to the Stroud Robbery on August 2, 1915. He was sentenced to 25 years and transferred to the Oklahoma State Penitentiary at McAlester.
While in prison, Starr spoke out against a life of crime, urging young people to stay honest. He was paroled on March 15, 1919.
For two years, he lived an honest life, even starring in "A Debtor to the Law," a film depicting the Stroud robbery and the senselessness of crime. He turned down an offer from Hollywood due to fears of extradition for the Bentonville robbery. During this time, he married his third wife, Hulda Starr, and moved to Claremore, Oklahoma.
However, Starr couldn’t resist the allure of his former life. On February 18, 1921, he and three companions robbed the People’s State Bank in Harrison, Arkansas, of $6000.
During the robbery, Henry was shot in the back by the former president of the bank, and his partners fled. He was taken to jail, where doctors removed the bullet.
On February 21, 1921, he boasted to doctors, "I’ve robbed more banks than any man in America." The next morning, he died from his wound with his wife, mother, and son at his side.
Henry died as he had lived, violently, but true to the code of the outlaws. He never revealed a single partner in any crime and never shot anyone during a crime.
During his 32 years in crime, he claimed to have robbed more banks than both the James-Younger Gang and the Doolin-Dalton Gang combined. He started robbing banks on horseback in 1893 and ended up robbing his last in a car in 1921. He allegedly robbed 21 banks during his outlaw career, making off with nearly $60,000, a fortune at the time.
The loot from Starr’s earlier crimes was reportedly hidden "near the border in a place nobody could find it in a million years." Many believe this cache is hidden somewhere along the Cimarron River in Stevens County, Kansas.