The Dalton family came from Jackson County, Missouri. Lewis Dalton was a salon keeper in Kansas City, Kansas, when he married Adeline Younger, the aunt of Cole and Jim Younger. By 1882 the family lived in northeast Oklahoma, and by 1886 they had moved to Coffeyville in southeast Kansas. When the Oklahoma Territory opened for settlement in 1889, the family claimed homestead land near Kingfisher. Thirteen of the couple's 15 children survived to maturity. One son, Frank, was a U.S. Deputy Marshal who was killed in the line of duty in 1887. Perhaps hoping to avenge their brother's death, the three younger Dalton boys--Grattan (b. 1861), Bob Dalton (b. 1869), and Emmett Dalton (b. 1871)--became lawmen. But in 1890, the boys moved to the other side of the law.
Bob Dalton was always the wild one. He killed a man for the first time when he was just 19. He was a deputy at the time and claimed the killing was in the line of duty. Some suspected, however, that the victim had tried to take away Bob's girl. In March 1890, Bob was charged with introducing liquor into Indian Territory (now Oklahoma), but he jumped bail and did not appear for his trial. In September 1890, Grat was arrested for stealing horses--a lynching offense in a time when horses provided the main mode of transportation--but either the charges were dropped or he was released.
Discredited as lawmen, the Daltons soon formed their first gang. Bob recruited George "Bitter Creek" Newcomb, Bill McElhanie, and "Blackfaced Charley" Bryant to ride with him and his brother Emmett. Bryant received his nickname because of a gunpowder burn on one cheek. Grat Dalton was visiting his brother Bill in California when the gang was formed, but joined it later, as did Bill Doolin, Dick Broadwell, and Bill Powers. Their first robbery target was a gambling house in Silver City, New Mexico.
On February 6, 1891, after Bob Dalton had joined his brothers in California, a Southern Pacific Railroad passenger train was held up. The Daltons were accused of the robbery, based on little evidence. Bob escaped and Bill was acquitted, but Grat was arrested, convicted, and put on a train headed for a 20-year prison sentence. According to one account, Grat was handcuffed to one deputy and accompanied by another. After the train had gone some distance, one deputy fell asleep and the other busied himself talking to other passengers. As it was a hot day, all the windows were open. Suddenly, Grat jumped up and dived head first out of the train window. He landed in the San Joaquin River, disappeared under water, and was carried downstream by the current. The deputies were astounded. Grat must have taken the key to the handcuffs from the first deputy's pocket as he slept and then timed his escape to take place when he knew the train would be on a bridge. If he had landed on the ground, he would almost certainly have been killed. Somehow he found his brothers and made his way back to Oklahoma Territory.
The Dalton brothers were now professional outlaws. Between May 1891 and July 1892 they robbed four trains in Indian Territory. On May 9, 1891, the men held up a Santa Fe train at Wharton (now Perry). They only got away with several hundred dollars, but they had worked well as a team. As they passed Orlando, they stole eight or nine horses. A posse soon took out after them, but the gang escaped.
Four months later the Dalton gang robbed a train of $10,000 at Lillietta in Indian Territory. In June 1892, they stopped another Santa Fe train, this time at Red Rock. Blackfaced Charley Bryant and Dick Broadwell held the engineer and fireman in the locomotive. Bob and Emmett Dalton and Bill Powers walked through the passenger cars, robbing the passengers as they went. Bill Doolin and Grat Dalton took on the express car. They threw the safe out of the train. Then with loot in hand, the robbers whooped and rode away. They gained little for their efforts--a few hundred dollars and some watches and jewelry from the passengers. The gang scattered after the Red Rock robbery, but it wasn't long until Blackfaced Charley was caught and killed in an escape attempt.
The gang struck again in July at Adair near the Arkansas border. They went directly to the train station and took what they could find in the express and baggage rooms. Then they calmly sat down on a bench on the platform, talking and smoking, with their Winchester rifles across their knees. When the train came in at 9:45 p.m., they backed a wagon up to the express car and unloaded all the contents. There was a large armed guard on the train, but for some reason all 11 men were at the back of the train. The guards fired at the bandits through the car windows and from behind the train. In the gun fight, 200 shots were fired. None of the Dalton gang was hit. Three guards were wounded and a town doctor was killed by a stray bullet. The robbers dropped out of sight, probably hiding out in one of several caves near Tulsa, Oklahoma.
The gang could have kept themselves busy with train robberies, but Bob Dalton wanted to make sure his name would long be remembered. He would, he claimed, "beat anything Jesse James ever did--rob two banks at once, in broad daylight." On October 5, 1892, the Dalton Gang attempted this feat when they set out to rob the C.M. Condon & Company's Bank and the First National Bank in Coffeyville, Kansas.
This article or an earlier version based on public domain text from the United States National Park Service [1].
