The Deadly Dalton Gang
The saga of the Dalton Gang, a notorious band of outlaws, unfolds across the American West, primarily in the territories of Oklahoma and Kansas, during the tumultuous years of 1890 to 1892. Often referred to as the Dalton Brothers, owing to the familial connection of three of its core members, this gang carved a dark legacy through a series of audacious bank and train robberies. Their story is one of shifting allegiances, from upholding the law to defying it, culminating in a dramatic and deadly confrontation in Coffeyville, Kansas.
The genesis of the Dalton brothers lies within a large family, the offspring of Adaline Younger Dalton and James Lewis Dalton. James Lewis Dalton, the family patriarch, journeyed westward from Kentucky to Missouri in the late 1840s, seeking new opportunities. By the 1850s, he had established himself as a horse trader and saloon owner in the bustling town of Westport, Missouri, now part of Kansas City. It was here that he met and married Adaline Younger. Notably, Adaline’s brother was the father of the infamous Younger brothers – Bob, Cole, and James – figures who would also leave their mark on the history of the Wild West.
The Dalton family expanded significantly, with Adaline and Lewis eventually raising fifteen children. Most of these children were born in Missouri before the family embarked on a westward migration to Indian Territory (present-day Oklahoma) in 1882. The family continued to move and in 1886 relocated near Coffeyville, Kansas. This region, marked by its untamed nature and history of violence, had a profound impact on the Dalton brothers. They were raised amidst the echoes of the bloody Missouri-Kansas border conflicts, where partisan groups like Quantrill’s Raiders roamed during the Civil War.
When the Oklahoma Territory opened for settlement in 1889, the Dalton family once again moved southward. Tragedy struck during the journey as James Lewis Dalton passed away, leaving Adaline to care for the younger children. Undeterred, she pressed on, staking a claim along the banks of Kingfisher Creek in Indian Territory. Initially, the family resided in a humble dugout, but by this time, the older Dalton brothers were independent and forging their own paths.
For a brief period, some of the Dalton brothers found themselves on the side of law and order, serving as U.S. Deputy Marshals. Frank Dalton, the eldest, received a commission as a deputy marshal for the federal court in Fort Smith, Arkansas. Bob Dalton also joined several of Frank’s posses. Frank’s life was tragically cut short on November 27, 1887, during a gun battle with the Smith-Dixon Gang, where he was fatally shot in the line of duty.
Grat Dalton followed in Frank’s path and was appointed Deputy Marshal in Fort Smith, Arkansas and then, two years later as a Deputy Marshal for the Muskogee court in Indian Territory in 1889. That same year, he was shot in the arm while attempting to apprehend a suspect. Bob Dalton also was also commissioned as a Deputy Marshal for the federal court in Wichita, Kansas, working in the Osage Nation in 1889.
Bob Dalton, who would later rise to become the leader of the Deadly Dalton Gang, possessed a particularly volatile temperament. At the young age of nineteen, he killed a man, claiming it was in the line of duty. However, rumors circulated that the shooting stemmed from a dispute over a woman.
Emmett Dalton, while occasionally assisting his brothers in their posses, primarily worked as a cowboy on the Bar X Bar Ranch near the Pawnee Agency in the Osage Nation. During his time at the ranch, Emmett crossed paths with two men who would later join the gang: Bill Doolin and William St. Power, also known as Bill Power or Tom Evans, who had arrived from Texas with a trail herd.
Emmett also befriended other cowboys working on nearby ranches, who would eventually become associated with the gang. These individuals included Charlie Pierce, George "Bitter Creek" Newcomb, Bill EcElhanie, Charlie Bryant, and Richard "Dick" Broadwell, also known as Texas Jack or John Moore. Charlie Pierce had fled Missouri to avoid jail time for bootlegging. Dick Broadwell, from a respected Kansas family, had claimed a homestead in Oklahoma Territory, only to be swindled by his wife and then embittered, he returned to Indian Territory and started working on ranches. George Newcomb, or "Bitter Creek," started working as a cowboy at the age of twelve. Charlie Bryant, known as "Black-Faced Charlie" because of a gunpowder burn on his cheek, came from Wise County, Texas.
The line between lawman and outlaw was thin in the Wild West. Bob Dalton and Emmett were charged with selling whiskey in the Osage Nation on March 21, 1890. To avoid trial, Bob and Emmett fled to New Mexico, forming their first gang and recruiting George "Bitter Creek" Newcomb, Bill EcElhanie, and "Blackfaced Charlie" Bryant. The gang committed its first robbery at a gambling house in Silver City, New Mexico, where they lost a game of faro and, believing they had been cheated, they took back their losses at gunpoint. Bob and Emmett then fled to California, where their brother Bill was a successful farmer and rancher.
In September 1890, Grat was arrested for stealing horses but was released due to lack of evidence. He lost his job as a Deputy Marshal but continued to work as a posseman for other deputy marshals for a time. Later, he joined his brothers in California.
Bill Dalton, who had previously lived a respectable life as a farmer and rancher, had become involved in local politics, and was angry with the Southern Pacific Railroad over land disputes. This is thought to be one of the reasons the brothers decided to rob a Southern Pacific train headed to Los Angeles on February 6, 1891. During the robbery, Bill kept the passengers from interfering by shooting over their heads, while the others forced the engineer to show them the express car. When the engineer tried to escape, he was shot and killed. Finding the express car, the guard refused to open the door and fired at them. Thwarted, the brothers gave up and rode away.
Bob and Emmett fled California with a posse on their trail, while Grat and Bill were arrested. Bob and Emmett returned to Indian Territory and joined Emmett’s old ranching buddies Charlie Bryant and Bitter Creek Newcomb. In May 1891, the four robbed a train at Wharton, Indian Territory, making off with $1,745. In California, Grat Dalton was found guilty of the train robbery and sentenced to 20 years in prison.
Three months later, Charlie Bryant became ill and was taken to the doctor in Hennessey, Oklahoma Territory. While there, Deputy Marshal Ed Short arrested Bryant while he was recovering from his illness at a local hotel. While being transported to the federal jail in Wichita, Bryant attempted to escape. In the ensuing shootout, both men were killed.
The Deadly Dalton Gang’s next robbery was the Missouri-Kansas-Texas Railway at Leliaetta, near Wagoner in Indian Territory. The gang consisted of Bob and Emmett, Bitter Creek Newcomb, Bill Power, Dick Broadwell, Charlie Pierce, and Bill Doolin. On the night of September 15, 1891, they robbed the express car of $2,500.
Back in California, Grat escaped while being transferred to prison. According to one account, Grat was handcuffed to a deputy. While the deputy was asleep, Grat stole the key to the handcuffs and jumped from the train, landing in the San Joaquin River. Grat made his way back to Oklahoma and rejoined the gang, while his brother Bill was still in California awaiting trial. Bill Dalton was acquitted on October 10, 1891.
The winter of 1891 was quiet for the Deadly Dalton Gang, but they teamed up with Pierce, Newcomb, Power, Broadwell, and Doolin to plan another train holdup. Waiting for the train at Red Rock, Oklahoma, on June 1, 1892, they sensed danger and let the first train pass, which was full of armed guards. However, they boarded the second train. Charlie Bryant and Dick Broadwell held the engineer and fireman while Bob, Emmett, and Bill Power walked through the passenger cars taking jewelry and cash. Bill Doolin and Grat Dalton robbed the express car, throwing the safe out of the train. They discovered the safe only contained about $50. Later, they found out that the first train had been full of armed guards protecting $70,000 of the Sac and Fox annuity.
On July 14, 1892, the Deadly Dalton Gang planned another train heist at Pryor Creek in Indian Territory. They took what they could find from the express and baggage rooms and waited for the train. The train was loaded with deputies, but they were all at the back of the train. The gang backed a wagon up to the express car and unloaded all of the contents, subduing the only armed guard. When the marshals discovered the robbery, a gun battle broke out where two guards were killed, as well as an innocent bystander. The gang escaped unharmed, making off with $17,000 in cash. After this train robbery, a prize of $5,000 was placed on each of the Daltons’ heads.
The Deadly Dalton Gang split up for a short time, but soon planned another robbery, this one to be their biggest yet. In early October 1892, brothers Bob, Grat, and Emmett Dalton, along with Bill Power and Dick Broadwell set out toward Coffeyville, Kansas. Arriving on the evening of October 4 at the P.L. Davis farm west of Coffeyville, they made camp and prepared for the next day.
On the morning of October 5, 1892, the five outlaws rode into Coffeyville to find the city’s streets filled with people. They tied their horses in an alley across from the banks, dismounted, and divided into two groups. Grat, Power, and Broadwell entered the C.M. Condon & Co. Bank, and Bob and Emmett crossed the plaza to enter the First National Bank.
Despite their disguises, a man named Aleck McKenna recognized them as Daltons. He watched them enter the bank and called out, "The bank is being robbed!" The cry spread, and the local townsmen armed themselves and took up positions to defend the town.
Inside the Condon Bank, the outlaws took C.T. Carpenter, Tom C. Babb, and Charles M. Ball hostage. Cashier Ball stalled them by claiming a time lock on the vault. Meanwhile, at the First National Bank, Bob and Emmett forced Thomas G. Ayers, W.H. Shepard, and B.S. Ayers to collect the money.
While waiting at the Condon Bank, bullets began to punch through the bank windows. Grat, Broadwell, and Power charged out of the bank into the plaza and were hit as they ran toward the alley. Bob and Emmett ran around a block, killing two citizens, and entered the alley at about the same time that Grat and the others got there.
Finding cover behind an oil tank, Grat fired several shots. Grat shot and killed Marshal Connelly. Bob Dalton was hit, slumped over, and died. John Kloehr killed Grat with a bullet in the neck. Power died nearby. Broadwell, mortally wounded, rode a half-mile before dying on the road.
Emmett, who was carrying the money bag, was hit in the arm, hip, and groin. He tried to reach his brother Bob, but Carey Seamen shot him in the back. Emmett surrendered and was taken to Dr. Wells’ office, where he was expected to die. However, he survived.
The gun battle lasted less than 15 minutes. Eight men were dead, and three were wounded. Four outlaws and four local men were killed. Emmett stood trial and was sentenced to life in prison but was pardoned in 1907.
On September 1, 1908, Emmett married Julia Johnson Gilstrap Lewis in Bartlesville, Oklahoma, and later moved to California. In California, Emmett worked as a building contractor and wrote a book about the Deadly Dalton Gang entitled "When The Daltons Rode." In May 1931, Emmett and Julia returned to Coffeyville for a visit, where they were treated like celebrities. Emmett died in Long Beach, California, on July 13, 1937. In 1940, the book was made into a movie starring Randolph Scott.
Coffeyville was not the end of the Deadly Dalton Gang story. Three members of the old gang remained at large: Bill Doolin, Bitter Creek Newcomb, and Charlie Pierce. Bill Doolin is thought by many historians to be a sixth member of the gang that hit Coffeyville, holding the horses in the alley, and the only member to have escaped. Bill Dalton also joined the former members of the gang, and they would terrorize the Territories for several years as the infamous Doolin-Dalton Gang.
George "Bitter Creek" Newcomb was shot by U.S. Deputy Marshals on May 2, 1894, in Oklahoma. Charlie Pierce was also killed by U.S. Deputy Marshals on May 2, 1894, in Oklahoma. Bill Doolin was killed in August 1896 by U.S. Deputy Marshal Heck Thomas near Lawson, Oklahoma. Bill Dalton was killed by lawman Loss Hart at Elk, Oklahoma, on June 7, 1894. U.S. Deputy Marshal Edward Short arrested Blackface Charlie Bryant in the summer of 1891. While being transported to Wichita, Kansas, on August 3, 1891, Bryant stole a gun and shot Marshal Short. Both men died.
“DALTONS! The Robber Gang Meet Their Waterloo in Coffeyville. The Outlaws Beaten at Their Own Game.” – Headline on the Coffeyville Journal on Friday, October 7, 1892