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A Good Boy Gone Bad: Bill Doolin

At the time of his death, dueling Bill Doolin was one of the hardest men the Old West ever saw, but he didn't start out that way.

A Good Boy Gone Bad: Bill Doolin

Quick with his guns, outlaw Bill Doolin headed up the most powerful outlaw gang in the Old West from 1892 to 1896. He drank hard, he rode hard, and he went down hard at the hands of lawman Heck Thomas. (Shooting Times photo)

Born in August 1858 in Johnson County, Arkansas, to parents Michael and Artemia Doolin, who were farmers, William Doolin was a good boy by all accounts. That is until he took up with questionable characters with names like George “Bitter Creek” Newcomb (a.k.a. “the Slaughter Kid”), Bill “Tulsa” Jack, Dan “Dynamite Dick” Clifton, and others. Doolin eventually went on to found the infamous Wild Bunch band of bandits (a.k.a. Doolin-Dalton Gang or Oklahombres or Oklahoma Long Riders).

Doolin left home in 1881, and his first run-in with the law was in Coffeyville, Kansas, in 1891. By then he had been cowboying in Indian Territory, and while in Coffeyville for some R&R—well, not exactly resting—Doolin and his compadres got drunk and made a public scene. When lawmen tried to confiscate their alcohol, a shootout ensued and two of the lawmen were shot. Doolin made a fast get-away and soon joined the Dalton Gang.

In October 1892, the Dalton Gang attempted to rob two banks simultaneously in Coffeyville. As I wrote in the December 2020/January 2021 issue, it didn’t go well for them because citizens of the town rallied together and shot it out with the outlaws. Four gang members were killed, and Emmet Dalton was captured. Historians disagree on whether Doolin was there and got away or wasn’t involved in the attempted robberies, but no matter. Doolin later formed his own gang, which came to be known as the Wild Bunch.

Between late 1892 and August 1896 when Doolin met his end at the hands of a deputy marshal, the Wild Bunch robbed various banks, trains, and stagecoaches in Arkansas, Kansas, and Oklahoma. During these robberies several shootouts occurred, and Doolin was shot in the foot. Also during these fracases, several lawmen, as well as bystanders, were injured and/or killed.


Under Doolin’s direction, the Wild Bunch was the most powerful outlaw gang in the Old West. Consequently, many lawmen and bounty hunters pursued the bandits. However, Doolin had somewhat of a Robin Hood image among locals because he and his gang preyed on wealthy institutions. The gang received considerable aid from the general public in eluding the lawmen and posses. In fact, two teenaged girls, known as Little Britches and Cattle Annie, followed the gang often informing them of the movements of law enforcement officers when they were being pursued.


On January 15, 1896, Doolin was captured by deputy marshal Bill Tilghman in Eureka Springs, Arkansas, but he escaped from jail on July 5 and hid out in Lawson in the Oklahoma Territory until August 24. On that day he said his final farewell after receiving a blast from Deputy U.S. Marshal Heck Thomas’s shotgun.

According to one writer, Thomas and a posse took up positions along a trail not far from a farmhouse near Lawson where Doolin was believed to have been staying. That night, Doolin came walking down the trail, leading his horse by the bridle reins and holding his Winchester rifle out in front of him, ready for a fight. Thomas called out for Doolin to surrender, and Doolin answered with a shot from his rifle. As the story goes, an instant later, Thomas centered Doolin’s chest with a load of buckshot from a 12-gauge L.C. Smith shotgun. Doolin was dead when he hit the ground.

By the end of 1898, all of the former Wild Bunch members were dead, having been killed in shootouts with the law. Doolin has been portrayed in several films and television shows by well-known actors, including Burt Lancaster, Robert Armstrong, Randolph Scott, Audie Murphy, Leo Gordon, and James Baker. He is buried in the Boot Hill section of Summit View Cemetery in Guthrie, Oklahoma.

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