Coffeyville Raid

Between 1890 and 1892, a band of outlaws roamed the American Old West under the name of the Dalton Gang, sometimes called the Dalton Brothers since three of its members shared that surname. These men made their living through robbing banks and trains. In 1892, they attempted to hit two banks at once in Coffeyville, Kansas, an operation that ended in disaster: two of the brothers along with two other members of the gang lost their lives. Emmett Dalton lived through the ordeal, was taken into custody, and eventually entered a guilty plea for second-degree murder, even though he would later insist he had fired no shots during the heist. He spent fourteen years behind bars before being granted parole.

Before turning to crime, the brothers Bob, Grat, and Emmett had worked on the right side of the law, first as lawmen under the federal court in Fort Smith, Arkansas, and afterward for the Osage Nation. A desire for greater profit led them into horse theft, and once that path grew too dangerous, they left the area altogether. From there they organized themselves into an outlaw band, turning their attention to robbing trains and banks. Their elder brother Bill Dalton never took part in the actual robberies, instead acting as a lookout and source of information for the group.

The wave of sensational stories surrounding the gang meant they were blamed for robberies far beyond their true reach, even though their real territory was limited mainly to California, Kansas, Oklahoma Territory, and Indian Territory. Countless legends and exaggerations grew up around their name. Following the deaths of Bob and Grat at Coffeyville, Bill Dalton went on to establish a new outfit alongside Bill Doolin, a group that became known as the Wild Bunch, or alternatively the Dalton-Doolin Gang.

Beginnings

All four brothers shared a father, James Lewis Dalton, who hailed from Jackson County, Missouri, with roots in Kentucky as well. While running a saloon in Kansas City, Missouri, he took Adeline Lee Younger as his wife. Adeline's connection to Cole and Jim Younger of the James-Younger Gang came through her half-brother, making her their aunt. Some have speculated that the Daltons drew inspiration from these notorious relatives, though the Youngers belonged to an older generation and were already behind bars during the years the Dalton Gang was active.

The Dalton siblings numbered twelve in total:

Charles Benjamin "Ben" Dalton, born 1852 and living until 1936 Henry Coleman "Cole" Dalton, who lived from 1853 to 1920 Littleton "Lit" Lee Dalton, spanning 1857 to 1942 Franklin "Frank" Dalton, born in 1859 and dying in 1887 Gratton Hanley "Grat" Dalton, whose life ran from 1861 to 1892 William Marion "Bill" Dalton, present from 1863 until 1894 Eva May Dalton, born 1867 and gone by 1939 Robert Rennick "Bob" Dalton, who arrived in 1869 and died in 1892 Emmett Dalton, born in 1871 and surviving until 1937 Leona Randolph Dalton, whose years stretched from 1875 to 1964 Nancy May Dalton, a life cut short between 1876 and 1901 Simon Noel "Si" Dalton, born 1878 and passing in 1928

Of these siblings, four went on to ride together as outlaws: Bob, Grat, Emmett, and Bill formed the core of the Dalton Gang.

Lawmen

On the twenty-seventh of November, 1887, deputy marshal Frank Dalton crossed the river from Fort Smith alongside fellow deputy Jim Cole, aiming to apprehend three men running whiskey. The bootleggers opened fire before the two lawmen could reach the camp. Frank managed to kill two of them before his weapon jammed, and the surviving bootlegger shot him dead. Cole, having taken a wound himself, fled the scene rather than stand by his partner. Frank now rests in a Coffeyville, Kansas grave.

Following Frank's demise, Grat left California to fill his late brother's post as deputy marshal at Fort Smith, bringing Bob into the fold as a member of his posse. By August of 1888, the pair had organized a posse targeting Charley Montgomery, a man accused of impersonating a deputy marshal. While Grat searched for the suspect around Coffeyville, Bob tracked him down in Timber Hills instead and pressed forward on his own initiative, determined to capture Montgomery before he could cross out of the territory. The ambush that followed left Montgomery dead.

By January of 1889, both brothers held deputy positions, serving initially under Marshal Jones before transferring to Marshal R.L. Walker's command in Wichita. Hoping to supplement his income, Bob took on additional work with the Osage Nation police, a force that offered the advantage of a fixed monthly wage, something the marshals office did not provide. Bob further brought Emmett onto his payroll to oversee the guarding of prisoners.

Outlaws

On a February night in 1891, specifically the sixth, two men wearing masks and armed with 44-calibre revolvers stopped a Southern Pacific passenger train close to Alila, California, a town now called Earlimart. Their faces stayed hidden throughout the holdup. Years afterward, Lit Dalton claimed that both Bob and Emmett had confessed to him repeatedly that they were the ones who committed this robbery.

Following the crime, Bob and Emmett took refuge in a barn on a ranch located a mile west of Malaga, where they spent the entire night in conversation with their brothers upon arrival. Lit confirmed that Grat's horse was genuinely limping and offered assistance in selling it, though its lameness meant it fetched only sixty dollars, leaving Grat without a replacement mount afterward. He sent his saddle and riding equipment ahead to Delano by rail and boarded a train bound for Traver, where his brothers awaited him. The trio gambled at poker through the night there, then repeated the exercise in Tulare. Their movements had been tracking the Southern Pacific payroll car on its route through the valley from Oakland toward Bakersfield, a train that typically drew gamblers and prostitutes in its wake; Grat and Bob had trailed this pay car together on multiple prior occasions.

For a fortnight after the holdup, the two fugitives concealed themselves in mountains near property belonging to their brother Bill, who supplied them with provisions and secured horses to aid their evasion. Nonetheless, lawmen caught up with Bill in Paso Robles, where Sheriff Kay placed him under arrest and transported him to Visalia. A hearing there bound him over for trial in connection with the Alila incident, though he managed to arrange bail and gain his freedom.

Kay then turned his attention to hunting down Bob and Emmett, enlisting his deputy Jim Ford in the effort. The trail led to the Dalton mother's residence, which Kay observed for several days before poor weather drove him back to Kingfisher. Upon his return the following day, he found that the brothers had already slipped away. He spent hours speaking with their mother, who went so far as to offer him breakfast while insisting her sons had done nothing wrong, describing them instead as lawmen, and suggesting he seek them in Guthrie.

Kay and Ford covered the fifty miles to that town, only to run into complications stemming from overlapping tribal jurisdictions. Their arrival at Guthrie coincided with evidence of a previous night's disturbance, the sight of three white men left hanging from a tree near the town's entrance, and sidewalks crowded with groups of black men shooting dice. Kay learned that Bob and Emmett had brawled in a local saloon, beating two cowboys severely before departing for Topeka. Duty called Kay back to California for Grat's trial, forcing him to abandon the chase, and the brothers, aided by numerous local friends willing to shelter them, easily shook off pursuit once back on familiar ground. Believing themselves free of Kay's attention, Bob and Emmett set about organizing what would become known as the Dalton Gang.

While his brothers spent four months evading Kay across the desert, Grat remained confined in the Tulare County jail at Visalia awaiting his day in court. Once free on bond, Bill traveled straight to Merced and retained John W. Beckenridge, considered the finest lawyer in the San Joaquin Valley, to represent Grat, unaware that this attorney also did consulting work for the Southern Pacific railroad. Meeting the two-thousand-dollar fee required Bill to liquidate nearly all his horses and mules. Their mother journeyed from Kingfisher to California as well, contributing to Beckenridge's payment by mortgaging her home and borrowing from neighbors, then traveling to Visalia accompanied by her daughters and sons Ben, Cole, Lit, and Bill for the proceedings.

The trial itself did not commence until June, stretching across three weeks. Testimony from multiple witnesses placed Grat in Fresno on the night of the robbery, yet the Southern Pacific's considerable influence tainted the proceedings against him. Beckenridge arrived intoxicated and behind schedule, and crucially, neither side raised the fact that the fireman's death had been accidental, caused by the expressman, information Grat lacked