You had to have a score card in the Old West, as lawmen turned outlaw and outlaws turned lawmen. Grat, Bob and Emmett Dalton - leaders of the infamous Dalton Gang - all wore badges before turning to the dark side. Grat was a U.S. marshal, Bob served as chief of police for the Osage Indians and Emmett was a deputy to both brothers at one time.
They reigned from 1890-1892, specializing in train and bank robberies. They were related to Jesse James, though they acted later and independently of the James Gang.
The Dalton family came from Jackson County, Missouri. Lewis Dalton was a saloon 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 Dalton, was a deputy U.S Marshal, killed in the line of duty in 1887. He had been tracking a horse thief in the Oklahoma Territory. When he located the suspect on November 27, 1887, he confronted him and a shootout erupted, resulting in Frank being killed. Perhaps hoping to avenge their brother's death, the three younger Dalton boys—Gratton "Grat" Dalton (b. 1861), Bob Dalton (b. 1869), and Emmett Dalton (b. 1871)—became lawmen.
But in 1890, the boys turned to the dark side. Bob, the wildest one, killed a man for the first time when he was 19. He was a deputy U.S. Marshal at the time and claimed the killing was in the line of duty but some suspected that the victim had tried to take away Bob's girlfriend. In March 1890, Bob was charged with introducing liquor into the Indian Territory. He jumped bail and did not appear at trial. In September 1890, Grat was arrested for stealing horses, a capital offense but the charges were dropped or else he was released. After being 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 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.
In February 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 given a 20-year prison sentence. According to one account, even though Grat was handcuffed to one deputy and accompanied by another while being transferred by train, he managed to escape by diving head first out of the train window. He landed in the San Joaquin River, disappeared under water, and was carried downstream by the current. 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 most 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). Passing 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 Powers walked through the passenger cars, robbing the passengers. Bill Doolin and Grat Dalton took on the express car. They threw the safe out of the train, gaining just a few hundred dollars and some watches and jewelry for their efforts. The gang scattered after the Red Rock robbery, but soon Blackfaced Charley was caught and killed in an escape attempt.
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 calmly waited for the train to arrive. 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 armed guards on the train, but for some reason they were at the back of the train. In the gun fight that ensued, 200 shots were fired. The guards fired at the bandits through the car windows and from behind the train. 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.
Not content with just robbing trains, Bob Dalton wanted to make sure his name would long be remembered. He bragged that he could "beat anything Jesse James ever did—rob two banks at once, in broad daylight." And on October 5, 1892, the Dalton gang attempted to do just that when they set out to rob the C.M. Condon & Company's Bank and the First National Bank in Coffeyville, Kansas. They disguised themselves by wearing fake beards but they were still recognized by one of the townspeople.
While the gang was busy trying to hold up the banks, the people armed themselves and prepared for a gun battle. When the gang exited the banks, a shootout began. Three townspeople got shot and town Marshal Charles Connelly was killed when he ran into the street after hearing gunfire. Grat Dalton, Bob Dalton, Dick Broadwell and Bill Powers were killed. Emmett Dalton received 23 gunshot wounds and survived. He was given a life sentence in the Kansas penitentiary in Lansing, Kansas, serving just 14 years before being pardoned. He moved to California and became a real estate agent, author and actor, and died in 1937 at age 66.
Bill Doolin, "Bitter Creek" Newcomb, and Charlie Pierce were the only members left of the Dalton Gang, although none was present at the Coffeyville shootout. It was suggested later that there had been a sixth man holding horses in an alleyway and that he had escaped. That man was believed to have been Bill Doolin but it was never confirmed.