The Dalton Gang and the Coffeyville Raid

From Lawmen to Outlaws

The Dalton brothers were not born outlaws. Their mother, Adeline Lee Younger, was the half-aunt of Cole, Jim, John, and Bob Younger — the brothers who had ridden with Jesse and Frank James through the 1870s. By the late 1880s, three Dalton brothers were wearing badges in Indian Territory. Frank Dalton served as a deputy United States marshal under Judge Isaac Parker at Fort Smith, Arkansas, and was shot dead on November 27, 1887, near the Arkansas River while attempting to arrest a whiskey runner named Dave Smith. He was twenty-eight.

His younger brothers Grat, Bob, and Emmett all followed him into federal service. Bob Dalton, by 1889, was chief of the Osage Indian police. What turned them is a matter of some dispute. The family maintained they had been cheated of pay for witness fees and horse hire, a grievance with documentary support in the Fort Smith records. By 1890, all three had crossed the line. Bob and Emmett fled to California with their brother Bill after the attempted train robbery at Alila, California, on February 6, 1891, in which fireman George W. Radliff was killed. Grat Dalton was tried for that killing in Visalia in 1891, convicted, and escaped before sentencing.

The Train-Robbery Year

Between May 1891 and July 1892, the reconstituted Dalton Gang — Bob, Grat, and Emmett Dalton, together with Bill Doolin, Charley Bryant, Dick Broadwell, Bill Power (sometimes spelled Powers), and several rotating associates — robbed at least four trains across the Oklahoma Territory: the Santa Fe at Wharton on May 9, 1891; the Missouri, Kansas, and Texas at Leliaetta on September 15, 1891; the Santa Fe at Red Rock on June 1, 1892; and the Katy at Adair on July 14, 1892. The Adair robbery, in which three railroad guards and two physicians in an adjoining building were wounded and one of the physicians killed, produced the largest coordinated lawman response yet mounted in the Territory.

By the late summer of 1892, Bob Dalton, who functioned as the gang’s leader, had concluded that train robbery was played out. He proposed instead something he believed would cement the Dalton name above that of the James gang: the simultaneous robbery of two banks in a single town. He chose Coffeyville, a Montgomery County, Kansas, railroad town of roughly 2,500 people just above the Oklahoma line. The Daltons had been raised on a farm four miles outside of Coffeyville. They knew it well. That was, in the end, the fatal problem: Coffeyville knew them well in return.

Twelve Minutes on the Plaza

The gang rode in from the south, up Eighth Street, at about 9:15 a.m. A city work crew had torn up the hitching rails at the plaza, forcing them to tie their horses in a narrow alley behind the Opera House — the alley that would, within the hour, pass into American memory as Death Alley. Bob and Emmett Dalton entered the First National Bank on the east side of the plaza. Grat Dalton, Broadwell, and Power crossed to the C.M. Condon & Company Bank on the west side. They carried Winchester Model 1873 lever-action rifles in .44-40 and Colt Single Action Army revolvers. Bob Dalton’s belt carried two Colts; Emmett’s carried one. The cartridges were interchangeable between rifle and pistol — the logistical elegance of the .44-40 cartridge was the reason the combination had become the working tool of the West.

They were recognized almost at once. A hardware clerk named Aleck McKenna, standing in his doorway on the plaza, saw Grat’s face through the Condon Bank window and shouted the alarm: “The bank is being robbed!” Within three minutes, Isham’s Hardware and Boswell’s Hardware, both on the plaza, had opened their gun racks to the citizens. Approximately a dozen townsmen armed themselves with Winchester rifles and shotguns and took up firing positions around the plaza.

Inside the Condon, cashier Charles Ball bought time by telling Grat Dalton that the vault was on a time lock — a lie, but a convincing one — that would not open for three more minutes. Those minutes killed them. When the gang emerged onto the plaza with two grain sacks containing roughly $21,000 in cash from the two banks, they rode into a crossfire. Bob Dalton shot liveryman John J. Kloehr’s neighbor Lucius Baldwin dead in the alley. Bootmaker George Cubine and his former partner Charles Brown were shot dead in front of Rammel Brothers Drug Store. Marshal Charles Connelly was shot in the back as he ran down the alley with a Winchester. Then the citizens closed the mouth of the alley.

John Kloehr, firing a Winchester Model 1873 at less than twenty paces, shot Bob Dalton through the chest. Bob sat down against a barn wall and died within the minute. Grat Dalton was shot through the throat by Kloehr a moment later. Bill Power was killed by a rifle ball from a position on the Opera House stairs. Dick Broadwell, mortally wounded but still in the saddle, rode half a mile south of town before falling from his horse. He was found dead within the hour. Emmett Dalton, his right arm shattered, took twenty-three buckshot wounds from barber Carey Seaman’s double-barreled shotgun but lived. The entire action, from McKenna’s shout to the last shot, occupied about twelve minutes.

“We came to rob the banks. We did not come to kill. But when they shot at us, we had to shoot back.” — Emmett Dalton, statement to the Coffeyville sheriff, taken from his hospital cot the evening of October 5, 1892.

The Afterlife of Emmett Dalton

Emmett Dalton recovered in the Farmers’ Home hotel under guard. He was tried in March 1893 in Independence, Kansas, pled guilty to second-degree murder in the killing of Lucius Baldwin, and was sentenced to life at the Kansas State Penitentiary in Lansing. He served fourteen years and was pardoned by Governor Edward W. Hoch on November 1, 1907. He married his pre-outlaw sweetheart Julia Johnson, moved to Tulsa, and later to Los Angeles, where he became a building contractor, a real-estate agent, and — not without a certain self-aware humor — a minor film actor and author.

His 1918 memoir Beyond the Law and his 1931 collaboration with Jack Jungmeyer, When the Daltons Rode, both of which he helped adapt to silent and sound film, remain indispensable primary sources for the raid, though they must be read with an awareness of the author’s ninety-degree turn from outlaw to moral essayist. He died in Hollywood on July 13, 1937, at the age of sixty-six.

The Firearms as Historical Record

The weapons recovered from the four dead Daltons and their associates were inventoried by the Coffeyville sheriff and by Wells, Fargo detectives on the afternoon of October 5, 1892. The inventory — preserved in the Montgomery County court records and reproduced in David Elliott’s contemporaneous account The Last Raid of the Daltons, published in Coffeyville in 1892 within weeks of the event — lists Winchester Model 1873 rifles in .44-40, Colt Single Action Army revolvers in both .45 Colt and .44-40 calibers, and a single double-action Colt Model 1877 “Lightning.” Several of these weapons were retained by the citizens who had ended the raid; others were held as evidence and later sold at the Dalton estate sale. A number passed, through the long channels of Western collecting, into private hands where documentation of their Coffeyville origin survives in period affidavits and photographs.

Gary Hendershott’s approach to Old West firearms authentication treats a Coffeyville-associated weapon the way a forensic examiner treats a piece of physical evidence: the serial number, the pattern of use, the documentary chain, and the survival of period photographs are all weighed against the physical condition of the object itself.

“The Dalton raid was the last gasp of the horseback bank-robbery era. After Coffeyville, the frontier closed around its outlaws.”

The End of an Era

The Coffeyville raid marked, historians of the West have long argued, the practical end of the mounted bank-robbery. The telegraph and the increasingly dense network of small-town railroads had reduced the distance an outlaw could put between himself and a posse within twenty-four hours. Communities armed themselves, and they organized. Bill Doolin, who had not ridden with the gang that morning — his horse had gone lame the night before, a detail on which his life turned — formed his own gang and was killed by a U.S. marshal’s posse near Lawson, Oklahoma, on August 25, 1896. The age of the long-rider was over within five years of Coffeyville.

Gary Hendershott and Old West Material

For more than fifty years, Gary has handled firearms, documents, and personal effects associated with the major figures of the American West — from Wild Bill Hickok and Wyatt Earp to the Youngers, the Jameses, and the Daltons. Coffeyville material, because of its narrow window of documentation and its close-grained forensic record, represents one of the most testable categories in all of Western Americana. A Winchester or Colt with a period chain of ownership to October 5, 1892, is not merely a firearm. It is a piece of evidence from one of the most thoroughly documented ten-minute episodes of the American frontier.