Bill Doolin: Last of the Old West Outlaws

William “Bill” Doolin was cornered. Visiting his wife near Lawson, Oklahoma, the famous outlaw was reportedly returning to his hideout “in the Creek country.” Deputy US Marshal Heck Thomas and his posse set upon Doolin as he exited his wife’s house. Surprised, the outlaw drew his pistol but was gunned down by a series of shotgun blasts. A contemporary newspaper report says Doolin “fell dead at the second round” after being ambushed by the four marshals.

Thomas had tracked Doolin to Lawson after the former Wild Bunch leader escaped from the Guthrie, Oklahoma jail, where he awaited trial. Doolin’s warrant carried a hefty reward for his capture, dead or alive. So ended the brief but active career of Bill Doolin, who led the Old West’s last major outlaw gang.

Bill Doolin Wanted Poster
Bill Doolin was the most wanted man in the West before his capture. (Public Domain)

A Trustworthy Cowboy

Bill Doolin drifted slowly into the world of bank and train robbers, beginning his adult life as an Oklahoma cowboy. Born in 1858, Doolin grew up in Arkansas but moved west at age 23 seeking work. He found it on Oscar D. Halsell’s H-X Bar Ranch on the Oklahoma Territory’s Cimarron River. Halsell reportedly liked Doolin and taught him to read and write, as well as basic arithmetic skills. Doolin eventually became a junior ranch foreman.

Doolin worked the H-X Bar and neighboring ranches for the next decade, gaining a reputation for being a trustworthy and capable hand. But Doolin also met and worked with several questionable characters during this time, notably members of the infamous Dalton Gang. It’s believed that Doolin occasionally helped them out for extra money, since cowboys weren’t exactly getting rich.

Doolin’s first brush with the law in 1891 was dramatic and decisive. He and several friends were celebrating July 4th with a keg of beer in Coffeyville, Kansas when they were confronted by several lawmen. It seems that Kansas was a dry state at the time and the cowboys objected to the officers busting up their keg. Shots were fired, wounding two lawmen. Doolin and his friends fled. Warrants were issued and Doolin left the cowboy life forever, joining the Daltons full-time.

The Outlaw Life

Doolin’s career with the Dalton Gang is hazy, though he did participate in the September 15, 1891, Lelietta, Oklahoma train robbery, which netted the gang $19,000. But gang leader Bob Dalton was stingy with the gang members’ shares, some said he blew much of it gambling, prompting Doolin and two others to quit.

Bill Doolin's Derringer
(schwendguns.us)

Historians believe Doolin still associated with the Dalton Gang, however, and some think he was the unknown sixth man when the gang was cut down in Coffeyville on October 5, 1892. The gang tried a daring double bank robbery that day, but the lawmen and citizens of Coffeyville were having none of it. Four of the five robbers were gunned down and the fifth, Emmet Dalton, was captured. A 6th man was said to have been seen holding the robbers’ horses in an alley, but he escaped. He may well have been Bill Doolin.

Doolin Takes Charge

Coffeyville marked the violent end of the original Dalton Gang, prompting Doolin to form his own outlaw gang, which he initially called the Oklahombres. They were also known as the Oklahoma Long Riders because of their long duster coats, and the Doolin-Dalton Gang, thanks to Doolin’s partnership with Bill Dalton, brother of the old Dalton Gang members. But their most enduring moniker was the Wild Bunch.

Doolin wasted no time, hitting the Ford County Bank in Spearville, Kansas on November 1, 1892. The Oklahombres got away with $1,500 in treasury notes and an unspecified amount of cash. Descriptions of the robbers soon circulated and the Stillwater, Oklahoma City Marshal recognized gang member Oliver “Ol” Yantis. A posse caught up to Yantis, where he was killed in a shootout on November 29, the first Oklahombre to be killed.

Doolin’s gang included several of his former Dalton Gang associates, and the soon-to-famous Wild Bunch began hitting banks, trains, stores, and stagecoaches in Oklahoma, Kansas, Arkansas, and Missouri. Two of Doolin’s most valuable weapons were two teenage girls who followed the gang and served as spies and lookouts. Jennie Stevens and Anna Emmaline McDoulet became famous in their own right as “Little Britches” and “Cattle Annie.” Doolin supposedly gave Jennie Stevens the nickname “Little Britches.”

Bill Doolin's grave marker
Bill Doolin’s Guthrie, Oklahoma gravestone. (findagrave.com)

The two girls were notable horse thieves and sold alcohol to Native American tribes. They dressed in men’s clothing and carried six-shooters on their hips. Both were captured by US Marshals in 1895. Little Britches was 16 and Cattle Annie was 13. Nothing concrete is known of Little Britches’ life after her parole, but Cattle Annie lived until 1978, dying in Oklahoma City.

Doolin the Family Man

Bill Doolin married Edith Ellsworth on March 14, 1893. There is some speculation about whether Edith knew Doolin was an outlaw, but she hailed from Ingalls, Oklahoma, which has been described as an “outlaw town” at the time. It seems that the townspeople and the bad guys had an understanding. The good citizens looked the other way to benefit from the outlaws’ free spending of their loot. The outlaws behaved themselves to preserve their hideout.

So, we can infer that Edith probably knew Doolin’s nature beforehand. We do know that Edith stayed with her husband until his death, and even moved around with him. Bill and Edith Doolin had one son, named Jay. His and his mother’s eventual fate is unknown to me.

The Battle of Ingalls

The Doolin-Dalton Gang’s most famous action was perhaps the September 1, 1893 “Battle of Ingalls.” The gang had been laying low in Ingalls for several weeks, and many were living in the local hotel and gambling in the saloon. Ingalls was a tiny town, with a population of about 150 people, so the outlaws were likely quite prominent, depending on the townspeople’s good will.

But word eventually reached US Marshal E.D. Nix that Doolin’s gang was in Ingalls. Nix dispatched a posse of 27 deputy marshals and Indian police to deal with them. The posse was camped near the town on the night of August 31, 1893, when they caught a young boy observing them. The marshals detained the boy overnight, but he slipped away the next morning and ran to warn the outlaws.

Doolin’s crew heeded the warning and saddled their horses in the local livery stable, but then inexplicably went back to their poker game in the saloon. Meanwhile, the lawmen worked their way into town. The outlaws’ first indication that something was wrong was when gang member George “Bitter Creek” Newcomb emerged from the saloon to mount his horse. He was immediately fired upon.

Ingalls, Oklahoma Ghost Town
Ingalls, Oklahoma was abandoned early in the 20th century and is now preserved as a ghost town. Left to right, you can see the saloon where the Wild Bunch were playing poker before the battle, the livery stable, from which they retrieved their horses, and the hotel from which “Arkansas Tom” Jones fired on US Marshals. (oklahomawonders.com)

Newcomb was wounded but managed to mount his horse and flee after fellow gang member “Arkansas Tom” Jones, who was sick in his hotel room, engaged the marshals from his second-story window. Jones hit and mortally wounded Deputy Marshal Thomas Hueston, who died the next day.

Responding to the gunfire, the gang erupted from the saloon behind a torrent of bullets, fighting their way to the livery stable. Outlaws Red Buck, Bill Dalton, and “Tulsa Jack” Blake mounted and burst from the stable, firing on the posse, the rest of the gang emerging in their wake. Deputy Marshal Lafayette Shadley shot Dalton’s horse from beneath him, but Dalton cut down Shadley, who died two days later. Doolin shot Deputy Marshal Richard Speed, killing him instantly. The gang escaped, though two more were wounded.

Jones was captured in his hotel room, surrendering when the marshals threatened to lob in some dynamite. He was tried, convicted, and sentenced to 50 years in federal prison. Jones was paroled in 1910 but was killed by Joplin, Missouri police in 1924 after robbing a bank. Three Ingalls townspeople were shot, one of them fatally. A man named Young Simmons was killed in the crossfire as he tried to take cover in a saloon. Another man was hit in the leg.

The saloon’s bartender, a man I can only find referenced as “Mr. Murray,” tried to fight for the gang, but it didn’t go so well. He aimed a Winchester rifle from the saloon’s doorway, but the lawmen fired first, hitting Murray in the arm and ribs. Murray was charged and sent to federal prison. He later unsuccessfully sued the government over the marshals shooting him.

In the end, three deputy marshals and one civilian were killed. Six more people were wounded. According to Marshal Nix’s report, “eight or ten horses were killed.”

On Doolin’s Trail

The Wild Bunch took time to heal and recover after Ingalls but hit the trail again early the next year. A string of robberies in January and March of 1894 prompted Marshal Nix to assign his three best deputies to bring the gang in once and for all. The deputies were the renowned Bill Tilghman, Chris Madsen, and Heck Thomas, later known collectively as the “Three Guardsmen.”

Nix wrote in their March 20 commission, “I have selected you to do this work, placing explicit confidence in your abilities to cope with those desperadoes and bring them in ­­— live if possible — dead if necessary.”

The Wild Bunch continued to hit stores and banks through the spring of 1894. Bill Dalton left in May to form his own gang, which robbed exactly one bank, in Longview, Texas. Dalton was tracked to his home in June and killed when he jumped out a window and charged the posse.

The Three Guardsmen
The so-called “Three Guardsmen,” L-R: Bill Tilghman, Heck Thomas, and Chris Madsen. (Public Domain)

The gang’s fortunes turned with an unsuccessful December robbery attempt and the Rock Island train robbery in April of 1895. Targeting the train’s $50,000 federal payroll, the gang, without Doolin, was unable to crack the safe, settling for robbing the passengers of cash and jewelry. Deputy Marshal Chris Madsen’s posse soon tracked them down, killing “Tulsa Jack” Blake and scattering the gang. Bounty hunters killed gang members Newcomb and Charlie Pierce a few weeks later.

A Deal With Doolin?

The pressure caused Doolin and “Little Dick” West to flee to New Mexico that summer. Tired of running, Doolin reportedly made several offers to surrender in return for half the bounty on his head and a lighter sentence. Those offers were rebuffed. Or were they?

January of 1896 saw Doolin back in his familiar haunts, though he was feeling his lifestyle’s negative effects. Relentless heat from Tilghman, Madsen, and Thomas kept him on the run, and his foot ached from a gunshot wound suffered years before. Picking up his wife in Kansas, Doolin traveled to Eureka Springs, Arkansas, to recuperate in the hot springs there.

The story goes that Tilghman was tipped off about Doolin’s presence at Eureka Springs, and single-handedly apprehended him in a bathhouse on January 15, 1896. The story immediately raised eyebrows. First, there were no known witnesses to the arrest. Accounts of the event also differ, with some saying Tilghman pulled a gun on Doolin, who came peacefully, and others asserting that the two men wrestled, with Tilghman winning. Even Tilghman’s accounts changed over the years, as he and his wife promoted his exploits through books and a movie, much of which has been debunked by historians and even some of his contemporaries. Chris Madsen noted that Tilghman never let facts get in the way of a good story.

Tilghman and Doolin were first seen together when Tilghman brought the famous outlaw to the Guthrie, Oklahoma jail by rail. Tilghman had wired Nix the previous day, saying “I have him. We will be there tomorrow.” An estimated 2,000 people showed up to witness Doolin’s arrival.

Deputy US Marshal Bill Tilghman
Deputy US Marshal Bill Tilghman. (truewestmagazine.com)

Second, Deputy Marshal Frank Canton noticed that Doolin arrived unrestrained — no handcuffs and no shackles. He was allowed to roam freely through the jailhouse. The lack of such precautions seems far out of place for a man like Doolin. Finally, Canton observed that Doolin seemed perfectly at peace with his situation, which does fit with his reportedly being tired of the outlaw life, but not of a man facing a long prison term.

Finally, a researcher named Nancy Samuelson, who wrote a respected book on the Three Guardsmen and Marshal Nix, says Tilghman was hundreds of miles away when he received the tip about Doolin being at Eureka Springs. Samuelson says Tilghman could not have possibly arrived at the time he says he did. I have no information on where Tilghman actually was at the time. But the fact that a train could indeed cover the 208 miles between Eureka Springs and Guthrie in a day at least shows that quick travel was possible.

With no further information, I cannot judge whether Samuelson’s allegation is true or not. But I can say that prominent Western historians think highly of her book and its research. As noted, we know that Tilghman’s widow wrote a glowing biography of the famed lawman that significantly whitewashed the reality of Tilghman’s career, and pressured other writers for the next 40 years to adopt her version. Samuelson’s book pulled back the curtains on Tilghman’s shady side, and his record indicates that he would not have been above such a deal with Doolin. Do with that what you will.

Doolin and 13 others escaped the Guthrie jail on July 5, 1896. Rumor had it that Doolin’s escape was part of the deal he cut with Tilghman. There is no evidence to support that theory, though Doolin’s reported freedom in the jailhouse lends itself to the story. But if Doolin seemed content with his fate, why escape, knowing Nix would send everything he had after him? There’s no way to know. As far as we know, Doolin never spoke of any deal made between him and Tilghman.

End of the Line

Deputy Marshal Heck Thomas tracked Doolin to the area around Lawson, Oklahoma, where his wife, Edith, was known to reside. Heck’s posse ambushed Doolin as he left her house, ordering him to surrender. Doolin drew his pistol and was immediately gunned down. Whether he had broken a deal with Tilghman or not, it seems Doolin decided he didn’t want to go to prison.

By the time Bill Doolin was killed on August 24, 1896, only two Wild Bunch members were still at large. Marshals killed “Dynamite Dick” Clifton in November of 1897 and “Little Dick” West was killed the next April. The Wild Bunch was done.

Doolin’s corpse was displayed in Guthrie, where a photographer took two photos. Doolin’s widow and her brothers sold copies for 25 cents apiece, along with a poem she composed about her dead husband. The money was supposed to defray burial expenses, but the government paid for the embalming and burial to preserve the evidence. Doolin was buried in the Boot Hill section of Summit View Cemetery in Guthrie.

Books were written and movies were made about Doolin’s exploits. He appeared in at least one comic book, and the Eagles’ “Desperado” album was written with Doolin and the Dalton gang in mind, including the title track and the songs “Doolin-Dalton” and “Bitter Creek.” The excellent 1969 Western, “The Wild Bunch,” is a fictional story, not based on Doolin’s gang of the same name.

Bill Doolin comic book
Bill Doolin’s exploits inspired books, movies, songs, and at least one comic book, which puts forth an interesting take on why Doolin may not have been with the Dalton Gang on the ill-fated Coffeyville, Kansas raid. Note the devil in the background pulling Doolin to his eternal reward. (crimewave.de)

Doolin’s Wild Bunch was the last big outlaw gang in the West. The 1890s saw America progressing past the time of horsemen robbing banks and trains. The Great Depression saw a brief resurgence of mounted outlaws, but these rode automobiles, not horses. Bill Doolin’s death marked not only the end of the Old West outlaws, but, more informally, the changing of the West as settled territory.

The Old West wasn’t what we see in the movies, but the outlaw gangs were real. Hardly romantic, these desperate men lived hard and mostly died young. Bill Doolin never saw 40. Perhaps it was a boon. One wonders how he, and men like him, would have fared in the 20th century.

William "Bucky" Lawson is a self-described "typical Appalachian-American gun enthusiast". He is a military historian specializing in World War II and has written a few things, as he says, "here and there". A featured contributor for Strategy & Tactics, he likes dogs, range time, and a good cigar - preferably with an Old Fashioned that has an extra orange slice.

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