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Doolin's Wild Bunch (Oklahombres)

Bitter Creek Newcomb
Bitter Creek Newcomb in a Guthrie funeral parlor.

Bill Doolin (William M. Doolin), the son of an Arkansas farmer, rode into the Indian Territory (later Oklahoma) in 1881, working as a cowboy at the H-X Bar ranch, where the Dalton Brothers occasionally worked. Doolin was a taciturn, tough cowboy who was quick with his gun, and he left the ranch after being involved in a shooting in Coffeyville, Kansas, in 1891. Two lawmen had tried to break up a beer party, and when they began pouring the brew on the floor, several cowboys, including Doolin, pulled their six-guns and fatally shot the two deputies. Doolin fled, joining the Daltons. Doolin participated in several train and bank robberies with the gang, but he escaped being killed with most of the Daltons on Oct. 5, 1892, when the gang raided two banks in Coffeyville.

Doolin missed the Coffeyville raid when his horse ostensibly pulled up lame and he told Bob Dalton that he would go to a nearby ranch to find another mount and join the gang later. By the time Doolin arrived at the Coffeyville city limits, the Daltons had died in a hail of bullets fired by irate citizens. Another story has it that Doolin quit the gang just before the Coffeyville debacle after arguing with Bob Dalton over how the spoils from the raid would be divided.

In 1893, Doolin married a preacher's daughter and then organized one of the most notorious outlaw bands in Oklahoma history - Doolin's "Oklahombres." The gang included Bill Dalton, one of the remaining outlaw brothers; Dan Clifton, known as Dynamite Dick; George "Bitter Creek" Newcomb; George "Red Buck" Weightman; Tulsa Jack Blake; Charley Pierce; Bob Grounds; Little Dick West; Roy Daugherty, also known as Arkansas Tom Jones; Alf Sohn; Little Bill Raidler; and Ole Yantis. From 1893 through 1895 the Oklahombres specialized in robbing banks. For three years this gang raided banks, trains, and stagecoaches, headquartering in the wide open town of Ingalls, Okla.

On May 30, 1893, Doolin and three of his gang robbed a train near Cimarron, Kan. As they were fleeing, a large posse led by the noted lawman Chris Madsen cut off the band and a wild gunfight ensued in which Doolin was shot in the right foot. The outlaws escaped under the cover of darkness. After a number of robberies, a small army of lawmen slipped unnoticed into the outlaw town of Ingalls on Sept. 1, 1893. Inside the Ransom and Murray saloon, Doolin, Dalton, Clifton, Weightman, Newcomb, and Blake were drinking heavily. Roy Daugherty went to his room on the second floor of the City Hotel. As the gang members sat down to a poker game, Newcomb stepped into the street to check the horses. Dick Speed, one of the deputies who had taken cover across from the saloon, impulsively fired a shot at Newcomb and the battle, of Ingalls commenced. Newcomb gave the alarm and then escaped by riding out of town in a hail of bullets. Meanwhile, the outlaws inside the saloon and Daugherty from his room fired their weapons from windows at the posse members.

William Blake ("Tulsa Jack")

Blake was a cowboy in Kansas during the 1880's, but later he wandered south and became a member of the Doolin gang. Late on the night of April 3, 1895, the southbound Rock Island Passenger train was stopped and held up about 1 mile south of Dover, OK, near the Cimarron River Bridge. The five outlaws in on the robbery that night were William Blake, known as "Tulsa Jack", Charlie Pierce, George "Bitter Creek" Newcomb, "Little Bill" Raidler, and George "Red Buck" Waightman. All were members of the notorious Bill Doolin gang.

The gang ordered that the express car be opened but messenger J.W. Jones refused. The outlaws fired about 20 rounds into it with their 45-90 caliber Winchesters. In a shower of wood splinters and glass, Jones held to his station until random bullets struck him in the leg, arm and wrist. Fearing the bandits would kill the entire train crew, the conductor finally persuaded Jones to open the car. Jones, however, could not open the "through safe" which had been locked in Kansas City. It could only be opened by express agents at the final destination of Ft. Worth where a large amount of money in the safe was destined for a military payroll. While Charley Pierce and "Bitter Creek" Newcomb kept an eye on things outside the train, "Tulsa Jack" and "Red Buck" patrolled the three coach cars containing about 250 people. They ushered the train's porter along and collected the passenger's wallets, watches and jewelry in an empty grain sack. "Tulsa Jack" walked behind him holding a gun to his back while "Red Buck" walked backwards to cover the rear. They collected about $400 cash and some jewelry and rode away into the night. The train moved on toward Kingfisher, 10 miles south, where a report was wired to Deputy Marshal Chris Madsen's office about 25 miles further down the line in El Reno.

As the gang rode northwest, confident that a pursuit could not quickly be mounted, Madsen rounded up his deputies in El Reno and formulated a plan the gang did not expect. The Rock Island provided an engine with a boxcar hooked behind the tender. At about 3:00 A.M., with their saddled horses aboard the special train, Madsen and nine deputies pulled out of El Reno toward the robbery site in Dover, arriving at dawn within about four hours of the holdup.

After trailing the gang most of the morning, the posse split into two groups. Madsen led one west along the Cimarron and deputy William Banks, with six men, pushed on along a trail the bandits did not bother to hide. By mid-afternoon Banks and his men spotted the outlaws. They were barely 60 yards away in a grove of black jack trees, resting themselves and their horses. The deputies quickly shucked their rifles, dismounted, and called for the gang to surrender. "Tulsa Jack" Blake, who was apparently standing guard, spotted the lawmen and fired a first shot in their direction, alerting his slumbering comrades.

"Tulsa Jack" Blake was Bill Doolin's "right hand man", and considered by many to be his most loyal and stouthearted follower. He worked as a cowboy in Kansas during the late 1880s before moving south to Oklahoma Territory where he met Doolin. Blake participated in many of the gang's bank and train robberies and was a key figure in the fight against lawmen at Ingalls, Oklahoma, on September l 1893. There, marshals had the outlaws trapped in a local hotel, but when gunfire erupted, three deputy marshals were cut down and killed. "Tulsa Jack" shot his way out of the building, ran to the stable, freed the outlaws horses, and led them back to the hotel where the gang mounted up and sped away through a barrage of gunfire.

In another incident, Blake, known to be "as quick with a gun as he was with cards", almost single-handedly enabled the gang's escape from a bank robbery in South West City, Missouri, on May 20, 1894. Armed citizen's added to the heavy gunfire of lawmen in a street shootout as the gang left the bank. Blake's deadly accuracy was responsible for wounding several gun-wielding citizens who fired at the gang as it thundered down the main street and out of town. The daring "Tulsa Jack" covered their retreat and was the last to mount up and leave, but he would be the first to fall following the train robbery at Dover.

In a fierce gun battle lasting almost 45 minutes, Deputy William Banks later estimated that more than 200 shots were exchanged that day in the sand basin along the Cimarron River. He reported that each bandit was armed with two revolvers and that their rifles were model '86 Winchesters in 45-90 caliber. Midway through the melee, "Tulsa Jack" scrambled toward one of the outlaw's downed horses. Deputy Banks took careful aim with his rifle and fired a shot that sent "Tulsa Jack" sprawling. He was killed instantly by a bullet that hit him in the back and came out near his heart. As the firing continued, two more bandits were wounded and another of their horses killed. The gang then withdrew; escaping down a hollow that could not be covered by the deputies.

The death of "Tulsa Jack" was just the beginning of a violent end to the Bill Doolin gang. A month later on May 2, "Bitter Creek" Newcomb and Charley Pierce were slain from ambush by reward seekers. A posse caught up with mortally wounded "Zip" Wyatt on August 3, 1895; he died in a jail cell one month later. On October 2, George "Red Buck" Waightman was also killed by marshals. By December 1896, 19 months after the Dover train robbery, both Bill Doolin and "Dynamite Dick" were fatally shot by marshals. "Little Dick" West died by gunfire in April of 1898 and "Little Bill" Raidler was crippled in a shootout with deputies, served prison time, and died a few years after his parole in 1903.

As Deputy Speed raced down the street, one of the gang members shot him dead. Errant bullets killed Del Simmons, a boy watching the fight, and struck another citizen in the chest. The guns fell silent for some minutes and one of the deputies called out to Doolin, asking him and his men to surrender. "You go to hell!" Doolin shouted back and the fighting again erupted. Doolin and his men then dashed to the livery stable, mounted their horses, and fired wildly at the lawmen who shot at them as they rode in the same direction as Newcomb. Bill Dalton was trapped behind a fence and lost his horse. Deputy Lafe Shadley ran forward to kill Dalton with a shotgun but Dalton whirled about and shot Shadley dead. Then Doolin reappeared, racing down the street on his horse, riding to the spot where Dalton stood. He pulled Dalton up on the back of his horse and the two raced out of town.

Daugherty was raised in Missouri in a highly religious atmosphere; his father was deeply devout, and his two brothers became preachers. But Roy rebelled against his family and ran away from home at fourteen. Calling himself "Tom Jones," he claimed that he was from Arkansas (thus his nickname) and hired on at an Oklahoma ranch. He eventually decided to get his money the easy way, and in the 1890's he joined Bill Doolin's gang of bank robbers. He was captured after the shootout at Ingalls, convicted of manslaughter, and sentenced to a fifty-year prison term.

Largely through the efforts of his brothers Roy obtained a parole in 1910. After running a restaurant in Drumright, Oklahoma, for two years, he went to Hollywood to act in Westerns. Later he returned to Missouri, and in 1917 he helped rob a bank in Neosho. He was again imprisoned, but in 1921 he was released. He immediately became involved in a bank holdup in Asbury, Missouri, and for three years he was a wanted man. In 1924, however, he was apprehended in Joplin and was shot to death while resisting arrest.

The gang continued their raids, the largest haul being about $40,000, taken from an East Texas bank, but their days were numbered as more and more lawmen took to their trail. The greatest lawmen of the day, Chris Madsen, Bill Tilghman, and Heck Thomas, formed posses and chased the Doolins through five states, never giving gang members a moment's peace, but the outlaws remained at large for well over a year.

Doolin was considered a fair-minded man and he reportedly saved Tilghman 's life one night by stopping the gang's arch killer, Red Buck Weightman, from shooting Tilghman from ambush. Tilghman's posse was close on the heels of the Doolins one morning. Doolin and his men had just eaten a large breakfast at a farmhouse. As the gang leader stepped outside, he saw Tilghman and his men riding down a distant hill toward the farm. The hospitable farmer thought that the Doolins were part of a posse. Doolin told him that "the other boys coming along now" would be hungry and would want breakfast, too, and that they would pay for all the meals. Tilghman and his men arrived, ate a hearty meal, and were then told by the farmer that "the other boys" had told them Tilghman would pay for the meals. The lawman reluctantly dug into his pocket and paid the farmer for the food his own men and the outlaws had eaten.

In Southwest City, Mo., on May 20, 1895, the Doolin gang raided a local bank, but J.C. Seaborn, the state auditor, seized a gun and tried to stop the bandits. He was dead and Doolin seriously wounded in the head when the outlaws rode from the town. A few weeks later, near Dover, Okla., the gang was camped near the Cimarron River when lawmen suddenly swooped down on them. Tulsa Jack Blake, on guard, warned the gang and traded shots with the posse. Blake was shot and died of his wounds as Doolin and the others escaped. By this time, there was little left of the Doolin gang. Most of its members had ridden off to their own bloody fates. Doolin's own end was also drawing near.

In January, 1896, Doolin was captured by Tilghman at the health resort in Eureka Springs, Arkansas, where the outlaw leader had traveled to find relief for his chronic rheumatism. The two men fought with fists until the powerful Tilghman knocked Doolin cold and arrested him. Tilghman brought his notorious prisoner to Gutherie, Okla., to stand trial for train and bank robbery. Thousands lined the streets of the town to catch a glimpse of the outlaw. Doolin was cheered as he was taken to jail. He vowed he would never go to prison, and some weeks later he engineered a mass jail break in which he and thirty-seven other prisoners escaped.

Riding to Mexico, Doolin hid out at the ranch of writer Eugene Manlove Rhodes, but he pined for his family and was determined to have his wife and child with him. He rode back to his family, who were then living in Lawson, Okla. On the night of Aug. 25, 1896, Doolin was approaching his father-in-law's farmhouse, where his wife and child were staying. Lawmen led by Heck Thomas, however, had learned of Doolin's presence in the area and were waiting in ambush. Doolin appeared on foot, leading his horse, carrying a rifle, whistling as he walked in the bright moonlit night. Suddenly Thomas shouted from behind some bushes, calling to the outlaw to surrender. Doolin raised his rifle which was shot out of his hand by several shots fired by posse. Doolin then drew his six-gun and fired twice before a blast from a shotgun fired by Deputy Bill Dunn and rifle bullets fired by Thomas cut him to pieces. The outlaw's body was later displayed, naked from the waist up, to show the many holes made by shotgun pellets.

In the 1890's Dan Clifton ("Dynamite Dick") switched from rusling cattle to bank robbery by joining Bill Doolin's "Oklahombres." After he was finally captured, he was incarcerated with Doolin in the jail at Guthrie. The two confederates bribed a guard in July, 1896, and after releasing a dozen other prisoners made good their escape. Clifton, however, was tracked down and killed by a posse a few months later.

George Newcomb ("Bitter Creek," "Slaughter's Kid") was reared in Fort Scott, Kansas, but as a youth he left home for Texas, where he worked for cattleman John Slaughter, thus acquiring the sobriquet "Slaughter's Kid." In 1883 Newcomb drifted into Oklahoma, where he hired on as a cowboy in the Cherokee Strip ranching country. He so frequently sang, "I'm a wild wolf from Bitter Creek And it's my night to howl," that his friends nicknamed him "Bitter Creek." He was a member of the Dalton and Doolin gangs and was involved in numerous train and bank holdups. At a country dance he met fifteen-year-old Rosa Dunn, giving her renown as "the Rose of Cimarron." Eventually he sought refuge at the Dunn Ranch, but Rosa's brothers killed him for the five thousand-dollar reward on his head.

George Weightman ("Red Buck") was a vicious killer and horse thief from Texas. During the 1880's he drifted into Oklahoma, and in 1889 he was arrested by Heck Thomas for horse stealing. Following a three-year prison term, he joined Bill Doolin's gang of bank robbers. On one occasion Weightman, in custody with two other prisoners, made a spectacular escape from a moving train. Although his two cohorts were killed and bullets were whizzing around him, Weightman jumped through a window and scrambled to safety. After a series of disagreements with Doolin, he was forced out of the band. He organized his own gang, but soon he was chased down and killed by lawmen.

Jack Blake
Doolin gang member Tulsa Jack Blake lies flanked by the lawmen who ended his crime career.

An educated man from Pennsylvania Dutch stock Bill Raidler (William F. Raidler "Little Bill") drifted into Texas and became part of the infamous Bill Doolin gang. Raidler had met Doolin in Oklahoma when they were both cowboys. A cowboy, convict, and robber of trains and banks, Raidler was involved in many gunfights, the most well-known of which took place in 1895. In Spring 1895, the Doolin gang was jumped by a posse near Dover, Okla. A forty-minute fray ensued in which nearly two hundred shots were exchanged. After Tulsa Jack Blake was killed, Raidler and three cohorts grabbed two horses and double mounting, galloped away to safety.

On May 20, 1895, the Doolin gang was robbing a bank at Southwest City, Mo., when irate citizens began to fire at them. As the bandits tried to flee, store owners Oscar and Joe Seaborn stepped out of their shop. Raidler rode past and fired at Oscar, but the bullet passed through Oscar's body and into Joe, killing him instantly. Near Elgin, Kan., on Sept. 6, Raidler was hiding out at Sam Moore's ranch when he was jumped at dusk by Bill Tilghman and two other law enforcement officers. Raidler fired back but was hit in the wrist by a rifle slug. Dropping his gun and running, Raidler was brought down by the bullets of Deputy W.C. Smith.

Wounded in the neck, both sides, and in the back, Raidler somehow survived. His final battle was near Bartlesville, Okla., in October 1895. Hiding in a cave, Raidler was discovered by Heck Thomas and two Osage scouts. When Raidler saw the men approaching, he ambushed them. Thomas fired back with a .45-90 Winchester and a bullet ripped into Raidler's hand. Dropping his rifle and racing into the bush, Raidler chopped off two of his damaged fingers and managed to hide in a tree to avoid capture. One week later he was wounded and apprehended by Tilghman and two other officers. Tried and convicted, Raidler served time and was later released on parole from an Ohio prison with the help of Tilghman. Raidler later married but never regained his health and lived out the rest of his years disabled.

Jay Robert Nash. Encyclopedia Of Western Lawmen & Outlaws . Da Capo Press. 1989.


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