Dalton Gang - Outlaws

Outlaws

Bob recruited George "Bitter Creek" Newcomb, Charley Pierce and Blackfaced Charlie Bryant to ride with him and his brother Emmett. Bryant received his nickname because of a gunpowder burn on one cheek. Grat was visiting his brother Bill in California when the gang was formed, but joined it later, as did Bill Doolin, Dick Broadwell, and Bill Power. Their first robbery target was a gambling house in Silver City, New Mexico.

On February 6, 1891, after Grat 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. Grat escaped and Bill was acquitted, but Grat was arrested, convicted, and given a 20-year prison sentence. According to one account, Grat was handcuffed to one deputy and accompanied by another while being transferred by train. After the train had gone some distance, one deputy fell asleep and the other busied himself talking to other passengers. It was a hot day, and 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. Grat found his brothers, and they made their way back to Oklahoma Territory.

Between May 1891 and July 1892, the Dalton brothers robbed four trains in the Indian Territory. On May 9, 1891, the men held up a Santa Fe train at Wharton (now Perry). They got away with several hundred dollars, only, but they had worked well as a team. As they passed Orlando, they stole eight or nine horses. A posse chased them, but the gang escaped.

Four months later the Dalton gang robbed a train of $10,000 at Lillietta, 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 Power 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. 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 soon Blackfaced Charley was captured by Deputy US Marshal Ed Short. While in route to be jailed in Wichita, Kansas, Bryant grabbed a gun from a railroad worker assisting Deputy Marshal Short, and in the ensuing gunfight Bryant and Short killed one another.

The gang struck again in July at Adair, Oklahoma, 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 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 were several armed guards 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.