Bill Doolin – Leading the Oklahombres
The annals of the American West are replete with figures who, for better or worse, etched their names into the historical narrative. Among these figures stands William M. "Bill" Doolin, a man who transitioned from a humble cowboy to the notorious leader of an outlaw gang that terrorized the Oklahoma Territory and beyond. Doolin, sometimes known as Will Barry, helmed a group known by several names: the Doolin-Dalton Gang, the Oklahombres, and the Wild Bunch, each moniker reflecting a facet of their audacious exploits. This article delves into the life and times of Bill Doolin, exploring his transformation, his criminal career, and the circumstances surrounding his eventual demise.
The late 19th century Oklahoma Territory was a land of opportunity and lawlessness, a place where fortunes could be made or lost, and where the line between right and wrong was often blurred. It was within this volatile environment that Bill Doolin rose to prominence, not as a law-abiding citizen, but as an outlaw who challenged the established order. His story is one of conflict, survival, and ultimately, a tragic end that cemented his place in the legends of the Wild West.
William "Bill" Doolin was born in 1858 in Johnson County, Arkansas, to Michael and Artemina Beller Doolin. His early life provided little indication of the path he would eventually take. As a young man of 23, he ventured westward, taking on various jobs to make ends meet. His journey led him to the H-X Bar Ranch, situated along the Cimarron River in the Indian Territory, around 1881. This ranch was owned by Oscar D. Halsell, a Texan who saw potential in the young Doolin. Halsell took Doolin under his wing, teaching him to read, write, and perform basic arithmetic. Impressed by his work ethic and willingness to learn, Halsell eventually promoted him to an informal foreman position on the ranch.
For nearly a decade, Doolin remained a working cowboy, gaining a reputation as a trustworthy and capable hand. He worked on several ranches in the area, interacting with other cowboys who would later become infamous outlaws. These included figures like George "Bitter Creek" Newcomb, Charley Pierce, Bill Power, Dick Broadwell, Bill "Tulsa Jack" Blake, Dan "Dynamite Dick" Clifton, and Emmett Dalton. These associations, though seemingly innocuous at the time, would prove to be a harbinger of Doolin’s future. The lure of quick riches and a life outside the confines of the law would eventually prove too strong to resist. The seeds of rebellion and the temptation of a life of crime began to sprout in the fertile ground of the Oklahoma Territory. It was only a matter of time before Bill Doolin would succumb to the allure of the outlaw life.
The year 1891 marked a turning point in Doolin’s life, setting him on a collision course with the law. While celebrating the Fourth of July in Coffeyville, Kansas, Doolin and his companions tapped a keg of beer. However, Kansas was a dry state at the time, and when lawmen attempted to confiscate the alcohol, a shootout erupted. Two lawmen were wounded in the exchange, prompting Doolin and his friends to flee the area. This incident transformed Doolin into a wanted man, effectively launching his career as an outlaw.
The infamous Dalton Gang, already notorious for their daring robberies, played a pivotal role in shaping Doolin’s trajectory. Though the extent of his involvement remains a subject of debate among historians, it is known that he associated with the gang and likely participated in some of their criminal activities. On October 5, 1892, the Dalton Gang attempted to rob two banks simultaneously in Coffeyville, Kansas. The audacious plan ended in disaster, with Bob and Grat Dalton, Bill Power, and Dick Broadwell all being killed in the ensuing gunfight. Emmett Dalton was the only survivor, later serving time in prison for his role in the failed robbery.
Bill Doolin was not present at the Coffeyville raid, a fact that undoubtedly saved his life. However, some historians have speculated that he may have been involved in a supporting role, possibly holding the horses in an alleyway. The identity of the sixth gang member, who escaped the scene, remains a mystery, but the possibility that it was Doolin cannot be entirely dismissed. Whether or not he participated in the Coffeyville debacle, the event had a profound impact on Doolin. It marked the end of the Dalton Gang as a cohesive force and paved the way for Doolin to establish his own criminal enterprise.
Following the demise of the Dalton Gang, Doolin formed his own gang, known as the Oklahombres, the Wild Bunch, or the Oklahoma Long Riders, the latter name a reference to the long dusters they favored. This group quickly became a terror in the region, specializing in robbing banks, stores, stagecoaches, and trains across Arkansas, Kansas, Missouri, and Oklahoma. The Oklahombres were a diverse group of outlaws, each with their own motivations and skills. Among its members were Bill Dalton, George "Red Buck" Waightman, Little Bill Raidler, Bob Grounds, Bill "Tulsa Jack" Blake, Richard "Little Dick West", Dan "Dynamite Dick" Clifton, Roy Daugherty (aka "Arkansas Tom" Jones), Alf Sohn, George "Bitter Creek" Newcomb, Charley Pierce, and Oliver "Ol" Yantis. Even two teenage girls, known as Little Britches and Cattle Annie, were associated with the gang, adding to their notoriety.
The Oklahombres wasted no time in establishing their reputation. On November 1, 1892, they robbed the Ford County Bank in Spearville, Kansas, making off with cash and over $1,500 in treasury notes. A description of the robbers was quickly circulated, and the city marshal in Stillwater, Oklahoma, recognized Oliver "Ol" Yantis. A posse was dispatched to apprehend him, resulting in a shootout on November 29, 1892, in Orlando, Oklahoma Territory, where Yantis was killed, becoming the first member of the gang to meet his end.
Despite his life of crime, Doolin found time for romance. On March 14, 1893, he married Edith Ellsworth of Ingalls, Oklahoma, in Kingfisher. Whether Edith was aware of Doolin’s outlaw status is unknown, but she remained by his side throughout his tumultuous life, and they eventually had a son named Jay.
The gang continued their spree of robberies, further solidifying their reputation as a force to be reckoned with. On June 11, 1893, they robbed a train near Cimarron, Kansas, escaping with approximately $1,000 in silver. A posse quickly pursued them, tracking them to a point north of Fort Supply, Oklahoma. In the ensuing gunfight, Doolin was shot and wounded in the left foot. Though he managed to escape and recover, he would walk with a limp for the remainder of his days. This injury served as a constant reminder of the dangers of his chosen path.
August 1893 saw several members of the Oklahombres, including Bill Doolin, Bill Dalton, George "Red Buck" Weightman, George "Bitter Creek" Newcomb, Charlie Pierce, "Arkansas Tom" Jones, "Tulsa Jack" Blake, and "Dynamite Dick" Clifton, seeking refuge in the small town of Ingalls, Oklahoma. They had been in town for weeks, residing at the local hotel and frequenting the Ransom Saloon. However, their presence did not go unnoticed.
Word of their whereabouts reached U.S. Marshal Evett Dumas "E.D." Nix, who assembled a posse of approximately 27 deputy marshals and Indian Police to capture the gang. The posse camped out along a creek the night before their planned raid. A young boy spotted them and was held overnight by the deputies. However, the boy managed to escape early the next morning and ran into Ingalls, warning the outlaws that "the marshals are coming."
On September 1, 1893, the posse entered Ingalls, leading to the infamous Battle of Ingalls. The gunfight resulted in the deaths of three of the fourteen lawmen carrying Deputy U.S. Marshals’ commissions. Two town citizens also died, one of whom was killed while protecting the outlaws. George "Bitter Creek" Newcomb was seriously wounded but managed to escape, while "Arkansas Tom" Jones, responsible for the deaths of the three deputies and one citizen, was captured. He was sentenced to prison, paroled in 1910, but later killed in Joplin, Missouri, in 1924 after robbing another bank. The Battle of Ingalls became a symbol of the intense conflict between lawmen and outlaws in the Oklahoma Territory.
Despite the setback at Ingalls, the Oklahombres continued their criminal activities. On January 3, 1894, Charley Pierce and George "Red Buck" Weightman robbed the store and post office at Clarkson, Oklahoma. Just weeks later, on January 23rd, the gang robbed the Farmers Citizens Bank at Pawnee, Oklahoma. On March 10th, they robbed the Santa Fe Railroad station at Woodward, Oklahoma, making off with over $6,000.
U.S. Marshal Evett Nix, determined to bring the Oklahombres to justice, tasked his best deputies – the Three Guardsmen – Bill Tilghman, Chris Madsen, and Heck Thomas – with taking down the Wild Bunch. On March 20th, Nix famously told them: "I have selected you to do this work, placing explicit confidence in your abilities to cope with those desperadoes and bring them in – live if possible – dead if necessary."
On April 1st, Bill Dalton and Bitter Creek Newcomb attempted to rob the store of retired US Deputy Marshal W.H. Carr at Sacred Heart, Oklahoma. Carr recognized Bill Dalton and reached for his gun. Newcomb shot Carr in the wrist, but the retired lawman wounded Newcomb in the shoulder. Dalton then shot Carr in the abdomen, but Carr continued to fight, chasing the fugitives outside before they fled on horseback.
The heists continued with a bank robbery at Southwest City, Missouri, on May 10, 1894, resulting in $4,000 stolen, one townsperson dead, and several wounded.
Bill Dalton eventually left the Doolin Gang to form his own gang. On May 23, 1894, his new gang robbed the First National Bank at Longview, Texas. However, it was his only robbery with this group. On June 8, 1894, a posse of lawmen approached Bill’s home near Ardmore, Oklahoma. Bill, armed with a pistol, jumped out of a window and ran towards the posse, ignoring orders to halt. He was killed immediately.
On December 19, 1894, Doolin was reportedly involved in an attempted robbery of the J.R. Pearce store at Texana, Oklahoma. However, they were driven off with less than $20.00 in merchandise.
On April 3, 1895, without Bill Doolin, the Oklahombres held up a Rock Island train at Dover, Oklahoma. They failed to open the safe containing $50,000 intended for the army payroll but robbed the passengers of cash and jewelry. U.S. Deputy Marshal Chris Madsen and a posse pursued them, picking up their trail at daybreak. "Tulsa Jack" Blake was shot dead while standing lookout, and the gang scattered.
On May 1, 1895, Charlie Pierce and George "Bitter Creek" Newcomb were killed by the bounty hunters known as "The Dunn Brothers." The Dunn Brothers were the older brothers of George Newcomb’s teenage girlfriend, Rose Dunn. It was rumored that Rose betrayed Newcomb, but it’s more likely that her brothers simply followed her to the outlaws’ hideout.
With the Three Guardsmen relentlessly pursuing them and gang members being killed, Bill Doolin and "Little Dick" West fled to New Mexico in the summer of 1895. Knowing his freedom was limited, Doolin attempted to negotiate a surrender in exchange for a light sentence, but his offers were rejected. Later that year, Doolin and his wife hid out near Burden, Kansas. On September 6, 1895, Little Bill Raidler was captured by Deputy U.S. Marshal Bill Tilghman. He was imprisoned and paroled in 1903 due to complications from wounds sustained during his capture. He died the following year.
From Kansas, Bill Doolin and his wife sought refuge in Eureka Springs, Arkansas, hoping the medicinal waters would alleviate the rheumatism in his previously wounded foot. However, Bill Tilghman tracked him to the resort and, in January 1896, single-handedly captured the outlaw without resistance. Doolin was taken back to Oklahoma and jailed in Guthrie to await trial.
While Doolin was in jail, Red Buck Weightman was killed on March 4, 1896, near Arapaho, Oklahoma Territory, by a Custer County Posse.
But Bill Doolin had other plans. On July 5, 1896, he, along with "Dynamite Dick" Clifton and 12 others, escaped from the Guthrie jail. Doolin sought refuge with his wife in Lawson, Oklahoma, while the other escapees scattered. His freedom was short-lived. On August 24, 1896, Doolin was tracked down and killed by Deputy U.S. Marshal Heck Thomas when he refused to surrender.
Doolin’s body was displayed in Guthrie, Oklahoma, and a local photographer captured two images of the deceased outlaw. Mrs. Doolin and her brothers composed a poem about him, printed it on postcards, and sold them with the photos for twenty-five cents each. The profits were intended for burial expenses, but the government ultimately covered the embalming and burial costs to preserve the body for identification purposes. He was buried in the Boot Hill section of Summit View Cemetery in Guthrie, Oklahoma. Doolin’s widow filed a $50,000 damage suit against the U.S. Marshals for her husband’s unlawful death, but it was dismissed in February 1897.
Dynamite Dick Clifton was tracked down by Deputy U.S. Marshals and killed near Checotah, Oklahoma, on November 7, 1897. "Little Dick" West, the last remaining fugitive gang member, was killed on April 8, 1898, by Deputy U.S. Marshals in Logan County, Oklahoma Territory.
Bill Doolin‘s life, though marked by lawlessness and violence, remains a fascinating chapter in the history of the American West. His story serves as a reminder of the complex and often contradictory nature of the frontier, where heroes and villains often blurred, and where the pursuit of justice could be as ruthless as the crimes it sought to punish.
Sources:
History.com
U.S. Marshals
National Park Service
Wikipedia