William "Bill" Doolin - Outlaw

William "Bill" Doolin 1858-1896

When it comes to outlaws of the Old West, none can compare to the cunning of the bandits who invaded the Twin Territories of Oklahoma and the Indian Nations. It was here that the badmen of the entire United States congregated. They were reckless and desperate, apostles of criminal liberty, ready at all times to commit any crime on the calendar. All were horse thieves, cattle rustlers, train robbers, and killers, and their operations made the territories notorious throughout the country. None were more infamous than the Doolin Gang. Their leader was an easy-going cowboy destined to ride into history as "King of the Oklahoma Bandits."
Fifty-year-old Michael "Mack" Doolin was a widowed sharecropper with three daughters and one son, when he moved from Newton County, Arkansas, to the northeast section of Johnson County after the death of his first wife in 1850. He married thirty-six-year-old Artemina Beller, and son William was born in 1858, followed by daughter Tennessee in 1859. By 1860, Mack had a small farm on the Big Piney Creek in Pilot Rock Township, about thirty miles northeast of present-day Clarksville, and this is where Bill and his siblings grew up. When Mack died in 1865, Bill helped his mother run the farm for the next several years.
In 1881, Bill decided to head west. He was twenty-three-years-old, and he had heard there were great opportunities for men willing to work. Already skilled with a saw and ax – tools most cowboys never learned to use – and an expert shot with rifle and pistol, he had no trouble signing on as a helper with a freight outfit bound for Caldwell on the Kansas frontier. Here, in 1882, he met Oscar D. Halsell, a Texas cattleman, who had the HH Ranch on the Cimarron River in a peaceful little valley thirteen miles east of present-day Guthrie. Doolin went to work for Halsell and his brother, putting his skills with saw and ax to good use building the corrals and structures needed. He easily became a top hand. Although he could neither read nor write, Halsell taught him enough that he could keep the ranch books. The two men liked and respected each other, and all accounts agree that Halsell considered Doolin completely trustworthy.
After the fierce winter of 1882-83 decimated the livestock, the Halsell brothers returned to Texas to replenish the herds. They had separate ranches on the Cimarron, but Doolin worked easily with each brother. Accounts disagree on Doolin’s activities for the next few years, but most claim he accompanied the Halsells.
Oklahoma today looks nothing like it did back in 1880. The Indian Nations had the entire eastern and southern half of the state, No Man’s Land was the entire panhandle, and the territory between the two was a hodge-podge of settled and unsettled pockets of thickly forested wilderness. The center section, which would become Kingfisher, Logan, Canadian, Oklahoma, and Cleveland Counties after the opening of the Cherokee Strip in 1889, were considered "Unassigned Lands," and large herds of cattle grazed here. It was a cattleman’s paradise, as the land was filled with lush vegetation and grasses, crisscrossed everywhere with cool rivers and streams.
In 1888, the government issued orders for cattlemen to vacate the land in the unassigned lands, which was to be opened to homesteaders in the spring of 1889. The Halsell brothers moved their herds east into the Iowa Nation and on up into the Cherokee Nation of Indian Territory, but Doolin drifted north, eventually finding his way to the Bar X Bar Ranch near the Pawnee Agency at the confluence of the Arkansas and Cimarron Rivers, where he stayed several months. By the Fall of 1888, he was employed by T. H. Hill of Arkansas City, Kansas, to work for the Wyeth Cattle Company. Although he rode into town for the usual cowboy relief, he was reportedly the most peaceful man in the whole outfit.
The great Oklahoma land rush of 22 April 1889 changed everything for all cow men. It was the first of the land runs, and it took place in the unassigned lands, to be followed a few years later by infamous race for the Cherokee Strip on September 16, 1893. As cattlemen were forced to vacate the open range in favor of the screaming, land-hungry masses of homesteaders and railroads, many young cowpokes were suddenly without jobs. That Spring, Doolin was once again forced to find new employment.
Tom Waggoner of Texas had secured grazing rights on the Osage Nation between Sperry and Hominy, northwest of Tulsa, and the new headquarters became the 3-D Ranch. It was one of the largest outfits in that area and employed a lot of men. Accompanying Doolin to the 3-D was Bill Blake (alias Tulsa Jack). Doolin remained with the 3-D until 1890, when Oscar Halsell opened a livery business and a wholesale grocery in the fledgling new town of Guthrie. He talked Doolin into coming to work in the livery for the winter of 1890-91, only Doolin did not like the confinement of town life. He returned to his old cronies on the Bar X Bar in the Spring of 1891.
It is impossible to talk of Bill Doolin without mentioning the Dalton brothers. Members were all one gang, originally under the leadership of Bob Dalton, until the Coffeyville, Kansas, raid in 1892 left Bill Doolin in control. All the men were about the same age – late-twenties to mid-thirties – and all were former ranch hands, cowboys caught up in the changing lifestyle brought about by the closing of the open range.
The Dalton brothers did not start out to be outlaws. The family moved frequently, from Missouri to Colorado to Kansas to the Indian Territory, in an effort to escape the difficulties brought on by the Civil War. They were poor, but not destitute, and no one has ever suggested that the trials of the war years ever influenced the Dalton boys to turn to crime. There were ten sons and five daughters born in the family, and by the time they moved to a farm eight miles north of Coffeyville, Kansas, in 1888 to await the opening of the Oklahoma land rush, several had married and moved away or had died. Father James Lewis Dalton and mother Adeline Lee Younger Dalton --- half-sister of Colonel Henry Younger, who fathered the famous Younger brothers --- may have bickered about the lack of money, but they were basically peaceful farm folks.
It would be romantic to say that the Dalton brothers were driven to a life of crime by being raised on the wild border lands of Indian Territory, but this is not true. Older brother Franklin became a United States Deputy Marshal under Judge Isaac Parker of Fort Smith, Arkansas. He was the only one of the family able to earn a decent wage, the others having to hire out to neighboring farms to toil in the fields for seventy-five cents per day. With no law west of St. Louis, and no God west of Fort Smith, it was his job, along with more than 200 other marshals aided by the various Indian Tribal Police, to try and keep order in the Twin Territories, something considered impossible by most lawmen in neighboring states.
The Twin Territories were a robbers’ roost of outlaws who cared nothing about human life or property, as long as they got what they wanted. There were too few marshals, a lack of money, long distances to travel, jails too few and far between, and a sympathetic factor among the honest folks for the gangs, as well as the rest of the honest folk living in fear of reprisal from the gangs. Although the marshals were hard pressed to do their jobs, and there were stumbling blocks galore, Frank Dalton was still able to track down and bring to justice most of the men he pursued. His death in an ambush in November 1877 was a real blow to his family and friends
It was hoped that several of Frank’s brothers would turn to law, and for a short time, Gratton Hanley, Robert Rennick, and Emmett were all model lawmen. Emmett had been only sixteen-years-old when Frank had died in a gun battle while trying to arrest members of the Smith - Dixon Gang of whiskey runners, but he was always ready to help form any posse. By 1889, Grat was a deputy for the Muskogee court and Bob a deputy for the federal court in Wichita, Kansas. Whenever his brothers needed men, Emmett, now working on the Bar X Bar, was the first to volunteer. When they discovered they could make more money by stealing horses and cattle, using their tin stars as shields, it set the Three Guardsmen on their trail.
The Three Guardsmen were United States Deputy Marshals Bill Tilghman, Chris Madsen and Heck Thomas, three of the most respected and admired lawmen who ever lived. Tilghman would earn the moniker of "the man who drove the outlaws out of Oklahoma." He was born at Fort Dodge, Iowa in 1854, moving to Kansas with his parents when he was two-years-old. When he was sixteen, he left home, migrating southwest to the frontier town of Wichita. He became a government scout during the Cheyenne and Arapaho Wars and suffered the loss of his home and all his possessions when Dull Knife lead his raid through the frontier of Kansas and Nebraska in 1878. When Dodge City was surveyed, he watched it grow into the wildest of all western towns, before becoming marshal for three years. His reputation for fearlessness was well known throughout the Twin Territories. In the Oklahoma Land Rush of 1889, he settled in Wharton (now called Perry), where outlaws tried to make it another Dodge City. It was inevitable that he would become a marshal in his new home.
Chris Madsen was born in Denmark and had been a soldier in the Danish Army before immigrating to the United States in 1870. He became quartermaster sergeant of the Fifth Cavalry and had charge of the Indian scouts, fighting in nearly every major Indian campaign in Arizona, Wyoming, Nebraska, Dakota, Idaho, Utah, Colorado, and Montana before becoming President Chester Arthur’s guide to the Yellowstone in 1883. He then "retired" to become Quartermaster Sergeant in the Field in the Twin Territories, settling on a homestead near El Reno, county seat of Canadian County, west of Oklahoma City. He was not destined to be a farmer. With the outlaws running rampant and making life miserable for everyone, he became a deputy marshal, earning a reputation "as a fighter who never showed the white feather."
Henry Andrew "Heck" Thomas was born in Georgia in 1850. When the Civil War broke out, he joined the Confederate Army at the age of twelve, becoming a courier in the Stonewall Jackson brigade. After the war, he took a job as an express messenger, and on a run between Galveston and Denison, he saved the company $22,000 by hiding it in the stove when the Sam Bass Gang struck. He took the job of deputy marshal, working out of Judge Isaac Parker’s court at Fort Smith, and like Tilghman and Madsen, his destiny was to rid the Twin Territories of the outlaw plague infesting it. On one occasion, he and Tilghman escorted forty-one prisoners to the federal court on the same train, all of them eager to escape. He was one of the most fearless men in the service of the government.
All three of these marshals had known and liked Frank Dalton, a well-respected marshal in his own right, and they had each worked with both Grat and Bob when the latter two were riding as deputy marshals. Tilghman had brought to justice more criminals than any other marshal working the Twin Territories, and Emmett Dalton would later write in his memoirs that Heck Thomas was their chief nemesis. After each raid, Thomas was in the field, after the gang, and he was closing in on them, when they met their destiny at Coffeyville. It would be Bill Tilghman who captured Bill Doolin.
Bill Doolin met Emmett Dalton and his brothers on the Bar X Bar. Also employed on the Bar X Bar was William St. Power (alias Bill Powers, alias Tom Evans). Power had drifted in from Texas with a trail herd from the Pecos. On the ranches nearby, Doolin came to know Charlie Pierce, George Newcomb (alias Bitter Creek Newcomb), Charlie Bryant (alias Black-Faced Charlie), and Richard "Dick" Broadwell (alias Texas Jack, alias John Moore).
A more miscreant lot cannot be found. Dick Broadwell came from Hutchinson, Kansas. At the opening of the Oklahoma Territory, he had staked a claim to a homestead next to a pretty young lady with a small homestead of her own. When she agreed to a marriage, both lands were sold, and the happy couple moved to Fort Worth, where the pretty lady promptly disappeared with all the money. With nowhere to go, Broadwell returned to the Twin Territories and started working the ranches. Charlie Pierce came from the Blue River country of Missouri. He fled to the Indian Nations to avoid the Fort Smith jail for whiskey peddling. Even among the outlaws, he was exceedingly wild. George Newcomb came from Fort Scott, Kansas. He began the life of a cowboy at the age of twelve, working for C. C. Slaughter on the Long S Ranch in Texas before drifting into the territories. Some accounts say his nickname was "Slaughter’s Kid." Charlie Bryant came from Wise County, Texas. He got his nickname from a black mark on his cheek from a powder burn.
Doolin’s first brush with the law happened that summer of 1891. Several of the cowboys decided to celebrate the holiday by riding over to Coffeyville, Kansas, and throwing a party. Up in the hills about a quarter of a mile from the main celebration, they sawed barrels in half and filled them with ice and beer bottles, conveniently ignoring that Kansas was a dry state, and beer was illegal. When Johnny Law showed up to confiscate the beer, there was a shoot-out, and two of the officers were wounded. From that moment on, Bill Doolin was an outlaw.
The Dalton brothers had already been riding the outlaw trails before Doolin pitched his camp with them. In March 1890, Bob and Emmett were arrested on selling whiskey to the Indians of the Osage Nation. Three months later, Bob, Grat, and Emmett were accused of horse stealing in Claremore, Indian Territory. At this point, Bob and Emmett fled to California to visit brother Bill, while Grat ended up in jail. When Grat was turned loose for lack of evidence, he immediately joined them.
All four Dalton brothers crossed paths with the law on the night of 6 February 1891. The Southern Pacific Railroad was held up in Alila, California, and although the robbery was botched, the fireman was killed. The Daltons were blamed. Grat was caught and tossed into jail on charges of attempted robbery. Bob and Emmett somehow managed to escape the dragnet and fled back to Oklahoma. Most accounts agree that brother Bill, born in 1863, was a victim of circumstances…the circumstances being the arrival of his three bandit brothers. Grat was found guilty of robbing the train and sentenced to jail, but he somehow escaped and made his way back to the territories. Brother Bill never recovered from the notoriety. He was a well-respected farmer and local politician before his brothers showed up, and although he never became a member of the Dalton Gang, most suspect that the embarrassment caused by the killing and attempted holdup turned him to crime. After the botched Coffeyville raid in 1892, which killed Grat and Bob and put Emmett behind bars, he would become part of the Doolin Gang.
The Dalton Gang took to train robbing as a profession. In May 1891, the brothers, along with Charlie Bryant and Bitter Creek Newcomb, robbed a train at Wharton (Perry) in the Oklahoma Territory, and it led to the death of Charlie Bryant. Some reports claimed that Deputy United States Marshal Chris Madsen was aboard the train, and that the gang members knew it. When they went car to car in search of him, he only escaped being killed by jumping off the back of the train and hiding in the darkness, until the gang robbed the express car and left. The train pulled out before it was safe enough for him to emerge from his hiding place, and all he could do was stare helplessly, as it disappeared down the tracks. Other accounts say it was Deputy Marshal Ransom Payne. In any event, the gang absconded with $1745 in cash, and the quick-thinking marshal soon had a posse on their trail. During the six week manhunt, Charlie Bryant became so ill that he was taken to a doctor in Hennessey. Deputy Marshal Ed Short recognized him and immediately placed him under arrest. Having no jail in Hennessey, Short decided to take his prisoner to Wichita. During the trip Bryant made a play for freedom. Grabbing a pistol, he shot it out with the marshal, and both men died from shots received from the other.
By September 1891, Bill Doolin had permanently given up the cowboy way of life. He was riding with the Daltons and robbing trains full time. His easy-going manner was also making him highly popular in the gang, which bothered leader Bob Dalton a great deal. Bob Dalton was twenty-two years old, young and wild, and Heck Thomas later said the outlaw was the best crack shot with a rifle that he had ever seen. On the night of 15 September, Doolin, Bob and Emmett Dalton, Bitter Creek Newcomb, Bill Powers, Dick Broadwll, and Charlie Pierce robbed the Missouri, Kansas & Texas "Katy" express car of $2500 near Waggoner, Indian Territory. Bill Doolin was now on his way, moving in and out the Twin Territories at whim.
During the Red Rock holdup on 1 June 1892, the gang narrowly missed an ambush of deputy marshals. The train was to be the same one they had robbed at Wharton, something the bandits considered to be really funny, but when the train pulled into the station, the coaches were all dark. Sensing something wrong, the gang allowed it to leave. As they prepared to ride out, another train pulled into the station, and they robbed it, getting only $50 for their trouble. Had they robbed the first train, they would have been met by Heck Thomas and a train full of deputies protecting $70,000 of the Sac and Fox Nation’s annuity, all eagerly wishing the Dalton Gang would strike.
Two months later, during the Adair, Indian Territory robbery of 14 July 1892, they once again unwittingly picked a train filled with deputies. All gangs had trademarks, something they did which would tell other gangs who was responsible for the crime. It was the outlaw way of bragging, but it served the added purpose of helping authorities identify the criminals and establish rewards for their capture. It was the trademark of the Dalton-Doolin Gang to leave the coaches alone to concentrate on the express car, at which time, they would then ride alongside and shoot into all the cars, killing or wounding anyone unfortunate enough to be in the way, a tactic guaranteed to delay the train at the station and allow the outlaws more time to escape. Thus, the marshals did not know the train was being robbed until it was almost all over. The gang worked swiftly and quietly and had almost succeeded in pulling it off, when they were spotted. A gun battle commenced, and one innocent bystander was killed and another wounded, but the gang escaped unhurt with an undisclosed amount of money. It was to be their last train holdup as the Dalton Gang.
The Dalton Gang came to an end on the morning of 5 October 1892. Feeling the pressure of the law on their heels, the brothers figured to make one last robbery and get enough money to leave the country. It was Bob Dalton’s plan to rob two banks in the same city at the same time, which would serve two purposes: 1) it would provide enough money to finance their escape into Mexico, and 2) it had never been done before and would be unexpected. He had always wanted to be as big a name in the annals of crime as the notorious James Gang in Missouri, probably because the Daltons were cousins to the Youngers, who rode with Jesse and Frank James, and he reasoned that the two-bank-robbery-scheme would make outlaw history. The only two banks he knew well enough to attempt such a plan were practically next door to each other in his home town of Coffeyville. Setting out from their hideout near Tulsa, the gang planned to rob both banks at the same time, something the James Gang had never attempted. What makes it so idiotic is that their faces were very well known to practically everyone in town.
Bob Dalton was correct about the law pressing in close. After the Adair robbery in July, the gang split up, knowing they would have a better chance to escape detection that way. Heck Thomas went after the Daltons, reasoning they would come back together with the rest of the gang sooner or later. He pressed the brothers, never letting them stay in any one place for very long. He trailed them into the Osage Nation and located their hideout on 3 October, but they had already pulled out, heading north. The next day, he followed the tracks to an abandoned campsite on California Creek, about twenty miles south of Coffeyville. On the morning of 5 October, as he trailed the gang toward Onion Creek outside town, news came that they had just been killed in the raid. He immediately went into Coffeyville and made the identification of the bodies for the Wells Fargo Company, but his job was far from over. With the death of the Daltons, a new gang emerged under a new leader, and he was soon embroiled in tracking down Bill Doolin and the Wild Bunch.
The raid on Coffeyville left a lot of questions unanswered. Even though they disguised themselves with false beards, the Daltons were easily recognized. Killed in the shootout were Grat and Bob Dalton, Bill Power and Dick Broadwell. Injured with shotgun blasts in the chest and in the back and not expected to live was Emmett Dalton, who eventually did recover from his wounds and who then served seventeen years in prison. When he was released, he would write his story and live the remainder of his life in California. All five members of the gang who rode into town were brought down by the citizens of Coffeyville, Kansas, who themselves suffered the loss of the town marshal and three other citizens in the raid. What has most historians so baffled is the identity of a sixth man suspected of being included in the raid. Heck Thomas had followed the trail of six riders, but he was pulled off the trail when news reached him that the gang had been killed. Was there a sixth man in the alley holding the horses, and was this mysterious rider Bill Doolin? Or did Bill Doolin, for whatever the reason, decide not to participate in the raid that day? Legend claims Bill Doolin sensed trouble and feigning a thrown shoe on his horse, pulled out at the last minute. No one really knows, and Emmett Dalton never told.
With the death of the Daltons, Bill Doolin took control of the remaining members of the gang. Including himself, there were still five members of the gang alive, and seven days after the raid, they sent a message to Coffeyville that they were coming to town to exact revenge. It threw the citizens into a panic. That night, the train at Caney, Kansas, just west of town, was robbed by four masked men. Everyone believed it was the newly formed Doolin Gang.
Bill Doolin was now the leader of his own gang. Besides Newcomb and Pierce, he also counted a young drifter named Oliver "Ol" Yantis and Richard "Little Dick" West. On the first job pulled by Yantis, the robbery of the Ford County Bank at Spearville, Kansas, they took $4,500. It was reported that West galloped up and down main street, yelling and shooting into buildings to panic everyone. The gang then separated to confuse the posse, and a few days later, Yantis was trailed to his sister’s farm at Orlando, north of Guthrie, by a posse composed of Heck Thomas, Chris Madsen, Tom Houston, and Chalk Beeson, the sheriff of Ford County, Kansas. The marshals took Yantis completely by surprised and killed him in an attack at daybreak.
By the end of the year, Doolin had more members in his Wild Bunch. It included his old pal from the 3-D Ranch, Bill Blake (alias Tulsa Jack), Richard Clifton (alias Dynamite Dick), George Waightman (alias Red Buck), William "Little Bill" Raidler, and Mason Frakes "Bill" Dalton, just in from California for the funeral of his brothers killed in the botched Coffeyville raid.
By the spring of 1893, the gang was in fine form. They had a growing reputation, large rewards on their heads, and they were becoming bolder and more ruthless. There is no real way to determine how many people died by their guns. It was also this Spring that Bill Doolin married. On 15 March 1893, he wed Edith Ellsworth in Kingfisher, the daughter of a preacher, and settled down at Ingalls, moving around as it became necessary to elude the law. Whether or not Edith knew he was an outlaw is not known, but she probably did. Throughout the remainder of his life, she stuck by him, keeping the marriage a secret and meeting him in secret. They had one son named Jay Doolin, who would later take the name of his step-father, Colonel Samuel Meek.
For a wedding present, the gang decided to rob the train at Cimarron, Kansas in June, where they shot the express messenger. Pursued by the posse, Doolin took a bullet in his left foot. Although he would recover from the wound, his injury would leave him with a limp. It would also plague him the rest of his life and ultimately play a role in his capture a few years later.
It was during this time that two teenage girls latched onto the gang. Annie McDoulet (alias Cattle Annie) and Jennie Stevens (alias Little Britches) had met members of the gang at a country dance, and they became camp followers. Cattle Annie was completely infatuated with Red Buck and would have done anything for him. Although they did not partake in the holdups, the girls were mighty handy as spies and messengers. They could also help drive the stolen horses and peddle whiskey.
Nineteen-year-old Roy Daugherty (alias Arkansas Tom Jones) also joined the gang around the summer of 1893. Unfortunately for Arkansas Tom, the marshals were closing in, and he did not have long to remain a member. He had come to Oklahoma Territory in his youth, taking a job as cowboy on a ranch in the Cheyenne country, and being acquainted with many of the men who rode with the gang, he easily fell into the outlaw way of life.
Lawmen had learned that the gang often rode into the little town of Ingalls (six miles east of Stillwater) to spend their stolen money, and they planned a surprise. On 1 September, two covered wagons swayed toward town. Inside were thirteen deputies loaded to the hilt with plenty of guns and ammunition. Marshal John Hixon was in command, and he scattered his men in strategic locations so that however the outlaws tried to leave town, the deputies would be able to cover them. Before the marshals were set, however, Bitter Creek Newcomb decided to investigate. He left his friends in the saloon, and sauntered down the street toward the livery, where Deputy Dick Speed spotted him and opened fire. Arkansas Tom, lying sick in bed in his hotel room, heard the commotion and promptly drilled the deputy. In the fierce battle that ensued, three deputies died, two innocent bystanders died, one bystander lay wounded, both Doolin and Bitter Creek were wounded, and Arkansas Tom was captured – after he ran out of ammunition. One of the marshals wanted to burn the hotel down to get him, but the owner protested. The rest of the gang got away..
It did not take the gang long to recover. In January 1894, Deputy Marshal Bill Tilghman found the outlaws quite by accident. He was not looking for the Doolin Gang; he was after cattle rustlers working in the area. While traveling along with a deputy, shivering in the icy blast, he spotted smoke coming from a snow bank. It turned out to be a dugout, a one-room "house" dug into the side of a hill. All Tilghman wanted was a place for himself and his deputy to spend the night. When he entered, the room was long and dark, except for a fire at his end. He could not see into the recesses, but he could feel the tension and animosity. Coolly, from a man sitting near the entrance, he asked for the location of Bill Dunn’s ranch, a known hideout for outlaws and whiskey peddlers. The man was surly and not particularly friendly, so Tilghman politely thanked him and walked out. Once out the door, he quickly drew his pistols, expecting to be shot, but nothing happened. He told his deputy to get out, that the place was full of outlaws.
The next morning, Tilghman returned with reinforcements, but the bandits had already cleared out. The unfriendly man from the evening before was now glad to see them. He told Tilghman that the outlaws had rifles trained on both of them, and he had been forced to be uncivil to save their lives. From the man, who turned out to be Bill Dunn, the man Tilghman had been seeking, Tilghman learned there had been eight outlaws in the dugout, including Doolin, Bill Dalton, Red Buck Waightman, Bitter Creek Newcomb, and Bill Raidler, and they had all cleared out right after Tilghman had left. Tilghman also learned something else. When he had walked out the previous evening, Red Buck had wanted to kill him. It was Bill Doolin who had saved his life.
The gang promptly robbed a bank in Pawnee, followed by a railroad station in Woodward in March. In April, Bob Dalton and Bitter Creek got into a shootout at Sacred Heart, and then seven members headed into Missouri in May to rob the bank in Southwest City. This particular robbery came close to being another Coffeyville for the outlaws. They robbed the bank, but had to shoot themselves free every inch of the way to escape, as law officers and citizens alike took up arms. At one point, two brothers, both outstanding citizens of the town, were shot with one bullet fired by Little Bill Raidler. It passed through the body of one brother, who lived to tell about it, and killed the other. Doolin received a buckshot wound in the forehead, and the gang made off with $15,000. They were forced to race through the Cherokee and Creek lands to get back to their hideout on the Cimarron.
Doolin thought the gang was too large to stay together, that it drew too much attention to themselves. He considered it safer to divide into small groups, meeting now and then at prearranged places. Bill Dalton and four others split off to form the Bill Dalton Gang, and they departed for Longview, Texas, where they robbed the First National Bank. In the getaway, one innocent bystander was killed and three others wounded. Lawmen tracked Dalton to his hideout near Ardmore, Indian Territory, and on 8 June 1894, Bill Dalton was killed by Deputy Lawson Hart in the resultant shootout.
The last job the Wild Bunch pulled as a gang occurred that April 1895. They boarded the Rock Island train at Dover, Oklahoma Territory, and proceeded to rob the express car. When finished, they leisurely headed west, unaware that the posse had quickly formed and was hot on their trail. Around two o’clock that afternoon, the posse, under the leadership of Deputy Marshal Chris Madsen, caught up with them at camp near Ames. In the resultant shootout, Tulsa Jack Blake died. The rest of the gang scattered and escaped, but they would never again re-unite as a gang.
The combination Dalton - Doolin Gang had now been active for nearly five years, and once friendly citizens began to turn on them. One of their favorite camps had always been the cave in the Creek Nation on the Dunn ranch on the Cimarron River. It lay about fifteen miles east of Ingalls, and the outlaws had been meeting there for years, unmolested. Although the Dunns were never part of the gang, they did provide shelter and give information about the movements of the deputies, as well as occasionally fence the stolen goods. But Bill Dunn was under pressure from the law, and he feared the day would come that he would be arrested as an accomplice, if he didn’t turn on the gang. In self-preservation, he became a special deputy, and he convinced his cousins, John and Dal, to help him set a trap for the outlaws. With the marshals offering huge rewards, it did not take long for the Dunns to agree to cooperate. Four members of the gang were supposed to be caught in the Dunn trap, but Dynamite Dick and Little Bill Raidler became suspicious, and at the last minute, they pulled out. On the night of 1 July 1895, the trap was sprung. Bitter Creek Newcomb and Black Face Charlie Pierce were the only two caught, and both were slain in their sleep. The Dunns took the bodies into Guthrie and collected the $5,000 reward money.
With so many of his friends now dead, Bill Doolin decided to leave the Twin Territories. Although he offered to surrender three different times to Marshal Evett Dumas "Ed" Nix in exchange for a light sentence, his offer was refused. With no other options, he reluctantly decided to rejoin his old friend Little Dick West, who had gone to New Mexico.
Little Dick was destined to have the longest career as an outlaw. He was barely sixteen, small and unassuming, when the foreman of the Three Circle Ranch in Decatur, Texas, found him and took him under his wing for the winter of 1881-82. The next Spring, he signed on with Oscar Halsell, who was moving a herd north to the ranch on the Cimarron east of Guthrie, and while working for Halsell, he got to become good friends with Bill Doolin. Little Dick stayed with Halsell until the ranch was abandoned in 1889, when the country was opened to settlement. Suddenly out of work, and too wild to settle down to the tame life of farming, he had drifted with Bill Doolin.
When the gang began to split up, Little Dick had headed west. He had found employment on the ranges of the Socorro County Panhandle, a stretch of land encompassing the San Andres Mountains west of Alamogordo, New Mexico, where a man could enjoy peace and quiet unmolested. It had been the lands of the Apache Chief Victorio only twenty-five years earlier and had seen the likes of the great Massai and the Apache Kid on more than one occasion. The Dalton boys had also used the area in their trips between California and Oklahoma. It was a perfect hideout for outlaws on the run, as sheriffs’ writs stopped short at the boundaries, and flight could easily be extended into Texas or Mexico when threatened. Bill Doolin remained several weeks in this outlaw paradise, while his attorneys tried to negotiate a peaceful surrender.
The beginning of the end came that Fall of 1895. In September, Marshal Bill Tilghman was able to capture Little Bill Raidler near Pawhuska. Although seriously wounded, Raidler stood trial for his part in the Dover robbery, was found guilty, and sentenced to prison for ten years. Paroled in 1903, he returned to Oklahoma.
Missing his family, Doolin left New Mexico. He was now the father of a two-year-old son, and he also had a bum leg from the shootout in Cimarron, Kansas two years earlier, so he was ready to give up the outlaw lifestyle. The only problem to "outlaw retirement" were the Three Guardsmen and Jim Masterson, all of whom kept a constant search for him and the remaining members of his gang.
Doolin unobtrusively crossed the Texas panhandle, and learning of the arrest of Little Bill Raidler by Bill Tilghman, he continued his trek north across the Oklahoma panhandle into southern Kansas. At about the same time, Edith Doolin disappeared from Lawson, a small town six miles west of Jennings, Oklahoma, where she had been living with her parents. It did not take Tilghman long to put the two pieces together. It could only mean that Bill Doolin was once again on the move.
Tilghman knew Doolin was back in the area, and with the full support and cooperation of every lawman in three states, he began a systematic search for the Doolin family. He started in Texas, then Indian Territory, and finally at a remote point in the Osage Nation, he learned of a woman and child headed to the Kansas border. He tracked them to a camp on a farm at Burden, about thirty miles northeast of Arkansas City. It was a place where Doolin was unknown, yet he knew the territory well.
When Bill Tilghman reached Burden, he was disappointed to find Doolin gone. It had been Doolin’s practice to go into town every couple of weeks for supplies, but he presented such a poverty-stricken figure that several ladies in the town had taken up a collection of money and provisions and had ridden out to present them to a surprised Edith. It so unnerved Doolin that he packed up and left in the dead of night, leaving his wife and child behind to pull Tilghman off the trail. It worked. Bill Tilghman spent many wasted days watching Edith, hoping Doolin would reappear.
On 6 January 1896, Edith Doolin and her son boarded a train back to her parents in Lawson. Satisfied that Bill Doolin was no longer in Kansas, Tilghman set out to find clues to where Doolin had gone. He discovered that the doctor in Burden had treated Doolin for his rheumatism, and one of the places discussed for a cure had been the sulfur baths in Eureka Springs, Arkansas. On 15 January 1896, Tilghman arrived in Eureka Springs, and one of the first men he spotted was Bill Doolin, using the alias of Tom Wilson, which was the same name he had used in Burden, Kansas. It was over in minutes. Tilghman arrested Doolin and brought him back to Guthrie to stand trial without a single shot being fired.
While Tilghman was tracking down Doolin, other deputies were hot on the trail of George Waightman, alias Red Buck. Not much is known about the outlaw’s early years, but after he joined the Doolin Gang, he was known to be meaner than a snake. He was a tall Texan horse thief with the reputation of a killer – a surly, vicious man who cared nothing for anyone. His hair was red, which gave him his nickname. In the Fall of 1890, Heck Thomas had arrested him for stealing mules in the Cherokee Nation, but he had escaped from the special prison car taking him to prison, and had not surfaced until he joined up with Bill Doolin. He killed for pleasure, and shortly after Doolin kept him from shooting Bill Tilghman in the back, Doolin tired of his cutthroat nature and tossed him out of the gang. Running on the fringes of the Wild Bunch, he ran into a desperado named George Miller, and the two of them finally shot it out with deputies Joe Ventioner and William Holcomb in March at a dugout near Arapaho. Red Buck was finally dead, and to prove it and because there were rewards totaling $4,800, his body was roped to an undertaker’s board, propped against a wall, and photographed.
Dynamite Dick Clifton was also on the edge of capture at that same time. The outlaw had killed two men in Arizona and had then made a dash for Texas. In June 1896, he was arrested in Paris, Texas, on a charge of selling whiskey illegally and sentenced to thirty days in the federal jail under the alias Dan Wiley. This was when Deputy Frank Canton finally caught up with him. When Canton first saw him, Dynamite Dick had not shaved in a month, and the heavy beard hid a scar on his neck the size of a half dollar. Canton duly sent for the barber, and Dick duly protested. With positive identification thus established, Canton produced the murder warrant and escorted his prisoner back to Guthrie to stand trial. Thanks to the law, Bill Doolin and Dynamite Dick were reunited. It was to be for the last time.
Eight days after Dynamite Dick arrived in the Guthrie jail, he and Doolin broke out, taking eight other prisoners with them. By the time the alarm was fully sounded, Bill Doolin had made it to the edge of town where his bad leg finally forced him to slow down. He headed for his old haunts along the Cimarron River, and one month later, Deputy Heck Thomas finally closed in. Confident that Doolin was hiding near his wife and son near Lawson, Thomas contacted the Dunn brothers on their Cimarron ranch, and the Dunns put him into contact with two blacksmiths from Lawson, who promised to keep an eye on the Ellsworth home. On 24 August 1896, Heck Thomas and his posse, which included his son Albert and Deputy Rufus Cannon, cornered Doolin on the road leading west out of Lawson, where his wife and child lived. According to all sources, Doolin had helped his wife load the wagon with all the family’s belongings and had then headed out of town with plans to meet up with his wife later at an undisclosed designated place. Accounts differ on what followed next, but the newspapers reported that Doolin was ordered to surrender, and when he opened fire on the posse, he died.
When the undertaker washed the body, he found twenty buckshot wounds in the chest, four having entered the heart, and one shot to the left arm. His body was dressed and placed on exhibition in Guthrie where hundreds of people viewed it. He was finally laid to rest in the Boot Hill section of Summit View Cemetery on Pine Street in Guthrie, Oklahoma.

Dynamite Dick Clifton lived only two months longer. After escaping from jail, and learning of the death of Bill Doolin, he met with Little Dick West, and the two of them headed south across the Cimarron River into the Creek Nation. The two outlaws hid for several weeks along the Deep Fork River, robbing several stores at the Sac and Fox Agency whenever they needed supplies, before joining the Jennings Gang. On 6 November 1896, twenty miles south of Sapulpa in the northeast corner of the Creek Nation, Heck Thomas and his posse encountered Dynamite Dick and several others in a ravine. A pitched battle ensued, but the outlaws managed to escape. The next day, near Checotah, Dynamite Dick was killed by the posse.
Eighteen months later, Heck Thomas, Bill Tilghman, Heck’s son Albert Thomas, Deputy Marshal William Fossett, Sheriff Frank Rinehart, and Guthrie police officer Ben Miller succeeded in tracking Little Dick West to the Fitzgerald farm near Guthrie, where he was working as a hired man. He was not at the main house, but knowing that another farm house lay about a half mile in one direction and a dugout in the side of a hill about the same distance in the opposite direction, the posse split up. Thomas and Tilghman headed for the dugout, Fossett and Rinehart for the other house, and Miller and Albert Thomas remained at the main house. Hearing a fierce gun battle coming from the other house, the other members of the posse arrived in time to see Little Dick shot to death by Fossett and Rinehart. He died on 8 April 1898, although his tombstone bears the inscription "killed 13 April 1898," which is incorrect. He was laid to rest near Bill Doolin and other outlaws in the Boot Hill section of Summit View Cemetery in Guthrie, Oklahoma.
Arkansas Tom was the only member of the Wild Bunch to live, but he was not destined to die from old age. He received a sentence of fifty years in prison after the Ingalls shootout, and when he was paroled for good behavior, Bill Tilghman got him a job in the store of an old friend. He later operated a restaurant in Drumright. When he visited retired marshal Evett Dumas Nix in St. Louis, Nix got him a job as an accountant. By 1916, he was back into trouble, his Oklahoma parole revoked, sent to prison in Missouri, and when he was released in 1921, he went back into crime. He died in a shootout with authorities on 16 August 1924 in Joplin, Missouri
The deaths of Bill Doolin and his Wild Bunch were tolling bells for the rest of the gangs who flourished in the Twin Territories. A new chapter opened in 1907 when Oklahoma was admitted to the Union. With statehood came increasing pressure to make life within her borders safe. Although it didn’t happen overnight, the days of the Oklahoma desperadoes came to an end.