“Would you shoot a brave man in the back?” — Part I

In a letter to H.P. Lovecraft, circa January 1934, Howard was educating the Gentleman from Providence on the ways of the west:

Of course, this rule works both ways. Men have been killed in the country in which they were born and raised, because they either could not or would not change their ways and adapt themselves to changing conditions. Sheriff Bill Tilghman met his death in that manner. He was the best law officer Oklahoma and Kansas ever had, to my mind. He killed only as a last resort. It was he who captured the famous Bill Doolin; and the outlaw admired him so much that he once prevented one of his men (Red Buck, or Weightman, a cold-blooded murderer) from shooting Tilghman in the back, when they had the drop on him. In 1924, when Tilghman was an old man, he accepted the job of marshal in an oil-boom town in Oklahoma, though warned by his friends that he was up against a brand of criminal he did not understand — the modern gangster rat. There was a Federal prohibition enforcement agent drunk and raising hell up and down the streets, and Tilghman, after urging him to go away quietly, arrested him bare-handed; and then, after disarming him, made the mistake of turning his back on him; the Federal officer, having gotten his training in civilization, drew another gun he had concealed, and shot Tilghman in the back. I often think of that contrast: Doolin, the outlaw, the bandit, robber, and killer, striking down Red Buck’s rifle, and exclaiming: “Would you shoot a brave man in the back?” And the civilized officer, himself sworn to uphold the law, shooting down an old man from behind with no more warning than a copperhead.

Howard’s Texas was populated with good men, bad men and some that were a bit of both. Two-Gun Bob was spot on with his account of the old time criminal versus the modern day bad man, but he somewhat embellished the death of Tilghman to make his point. But he did get the incident with Doolin right.

William Doolin was Arkansas-born; sometime in 1858 (the exact date is unknown). He was born on a homestead near the Big Piney River approximately thirty-five miles northeast of Clarksville.

Doolin’s father, Michael “Mack” Doolin was a sharecropper, raising three daughters and one son after death of his first wife in 1850. He soon married thirty-six-year-old Artemina Beller, and son William was born in 1858, followed by a daughter named Tennessee in 1859. William stayed near the family homestead until he turned 23 when he left to seek his fortune.

Looking for work, he went west in 1881 to Oklahoma and was hired as a cowhand by Oscar D. Halsell to work on his huge ranch. Halsell took a liking to the young man, taught him to write and do simple arithmetic and eventually made him an informal foreman on the ranch. Doolin worked for several other ranchers in the next decade and he was widely considered trustworthy and capable.

Doolin’s first run-in with the law came in the summer of 1891 while working as a cocrovwpuncher on the Bar X Bar Ranch. Several of the cowhands, including Doolin, thought it would be a good idea to celebrate the 4th of July holiday by riding into Coffeyville, Kansas and throwing a party. The group was enjoying a keg of beer when the law showed up. Kansas was a dry state. When the lawmen tried to confiscate the beer, there was a shoot-out, resulting in two officers being wounded. From that day on Doolin was a wanted man. During this period, Doolin and his friends rode with the Dalton Gang from time to time. Doolin also held something of a Robin Hood image. He was well liked by many, and he and his gang received considerable aid in eluding the law.

Doolin went on to form “The Wild Bunch,” which was also known as the “Doolin–Dalton Gang” or the “Oklahombres.” In addition to Doolin, other members of the gang included George “Bittercreek” Newcomb (aka “Slaughter Kid”), Charley Pierce, Oliver “Ol” Yantis, William Marion “Bill” Dalton, William “Tulsa Jack” Blake, Dan “Dynamite Dick” Clifton, Roy Daugherty (a.k.a. “Arkansas Tom Jones”), George “Red Buck” Waightman, Richard “Little Dick” West, and William F. “Little Bill” Raidler.

The origin of Doolin’s gang came about after a botched train robbery carried out by the Dalton Gang in Adair, Oklahoma Territory. The crime occurred on July 15, 1892, resulting in the death of two guards and the wounding of two townspeople. One of the townspeople died the following day. Bob Dalton decided to split the gang before going on the run, telling Doolin, Newcomb, and Pierce to return to their hideout in Ingalls, Oklahoma Territory. It was a lucky break for the trio because on October 5, 1892, the Dalton Gang would be wiped out in Coffeyville, Kansas.

On that fateful October morning, five members of the Dalton Gang (Grat Dalton, Emmett Dalton, Bob Dalton, Bill Power and Dick Broadwell) rode into the small town of Coffeyville. The Daltons had a bold objective in mind – to rob two banks simultaneously

But problems plagued the outlaws from the outset of their plan for financial security. A hitching post where they intended to tie their horses had been removed due to road repairs. The gang was forced to hitch their horses in a nearby alley — a fateful decision. Also, since Coffeyville was the Dalton’s hometown, two of the Daltons wore false beards and wigs. Of course, the locals quickly saw through the disguises — the gang was recognized as they crossed the town’s wide plaza, split up and entered the two banks.The locals armed themselves as the bold outlaws entered the two banks — Bill Powers, Dick Broadwell and Grat Dalton took the C.M. Condon Bank and Bob and Emmett Dalton walked into the First National Bank. Inside the Condon Bank, three employees are forced at gunpoint to fill a bag with money. One brave teller falsely tells to the robbers that the vault has a time lock and can’t be opened for another 10 minutes. Surprisingly, the robbers buy this story and decide to wait – a big mistake since as the townspeople open fire, shattering the front windows of the bank. Quickly ducking down, the trio of robbers returned fire and the gun battle was on. Trapped inside with no back way out, both bandits and bankers were forced to withdraw to the back room to avoid getting riddled with bullets, which were pouring into the building from the street like red-hot hail.

Meanwhile, it was pretty much the same scene at the First National Bank where Bob and Emmett Dalton forced the bank’s employees to fill a grain sack with money. The pair then used the employees as human shields, and attempted to escape the bank, only to be driven back inside by a blistering barrage from the townspeople’s’ guns.

They were forced back into the bank where Bob stepped to the door, raised his Winchester rifle, took deliberate aim and fired into the street. Emmett secured the money bag and then ordered the young men to open the back door and let them out.

As soon as Grat Dalton and his companions, Broadwell and Powers, left the Condon Bank they had just robbed, they came under the guns of the men in the nearby Isham’s Hardware store. The trio was attempting to make it to the back alley where their horses awaited them. However, Grat Dalton and Powers each received potentially mortal wounds before they had retreated twenty steps, but still managed to make a run for cover. Powers tried unsuccessfully to gain entry to several locked buildings, while Grat Dalton was able to crawl under an oil tank. Powers eventually made it to his horse, which was tethered in the alley – an alley that was soon to become a shooting gallery with the gang as the sitting ducks. Powers grabbed the reins and was struck in the back by another rifle bullet; he collapsed and died next to his horse.

Town Marshal Connelly ran into the alley in pursuit of the bandits, facing toward where the horses were hitched. This fateful movement left him with his back exposed to the murderous Grat Dalton who raised his rifle and shot Connelly in the back. The marshal fell dead, face first into the dirt just twenty feet from his unseen murderer.

Wounded in the back, Broadwell managed to reach cover in the Long-Bell Lumber Company’s yards, where he laid down to rest. Broadwell took advantage of a lull in the shooting, crawled out of his hiding-place and mounted his horse and tried to make a clean getaway. He was hit with rifle fire and buckshot before he had ridden twenty feet. Bleeding and dying, he clung to his horse and rode out of the city – his dead body was later found alongside the road a half-mile west of the city.

As Marshal Connelly fell dead in the alley, Bob and Emmett Dalton escaped the First National Bank – running down a side alley and into “death alley” from the north. When the two Daltons reached the intersection of the two alleys they discovered townsman F.D. Benson climbing through a rear window with a gun in his hand. Spotting his target, Bob fired at him point blank at a distance of not over thirty feet. The shot missed Mr. Benson, but struck a window and shattered the glass. Bob scanned the tops of the buildings, suspecting that the shots that were being fired at the time were coming from that direction.

As Bob looked for rooftop shooters, the men at Isham’s took deliberate aim at him from their position in the store and fired. At least one bullet found its mark, severely, if not fatally wounding the notorious leader of the Dalton Gang. He managed to stagger across the alley and where he sat down on a pile of dressed curbstones near the city jail. In desperation, he kept his Winchester in action and fired several shots from where he was seated – his aim was unsteady and the bullets went wild.

He shakily stood up and sought refuge alongside of an old barn west of the city jail. Leaning against the southwest corner, Dalton brought his rifle into action again and fired two shots in the direction of the hardware store. Meanwhile, John Kloehr, secreted behind his livery stable fence, drew a bead on the outlaw leader. A ball from his rifle struck the desperado full in the breast and he fell backwards, falling among the stones that covered the ground where he was standing.

Up to this point, Emmett Dalton had somehow managed to escape unhurt. He kept behind cover after he reached the alley until he saw a chance to make an attempt to mount his horse. A half-dozen rifles fired a barrage in his direction as he tried to get into the saddle, two bullets found their mark — Emmett was shot through the right arm and through the left hip and groin, but he succeeded in getting into the saddle. Still clinging to the sack containing the money they had taken from the First National Bank, Emmett boldly rode back to where Bob was lying, and reaching down, he attempted to lift his dying brother on the horse with him.

Cary Semans, the town barber, had just returned from a hunting trip and still had his shotgun in hand, and fired both barrels into Emmett’s back. The outlaw dropped from his horse, still clinging to the sack containing over twenty thousand dollars, falling near the feet of his brother, who died just seconds later. Amazingly, Emmett survived his grievous injuries and spent some 14 years in prison for his part in the raid on Coffeyville.

There has been much speculation as to the whereabouts of Doolin during the ill-fated Coffeyville bank robberies. The least feasible of these speculations is that he was watching the horses in the alley — a job for a low-level outlaw, which Doolin was not. Another possibility has Doolin skipping the raid after a falling out with the Dalton gang’s leader, Bob Dalton. Likewise, Bill Dalton skipped the raid, most likely figuring it was a bad idea to rob banks in his hometown where everyone knew who he was. But the pair did meet up after the killing of their fellow gang members and put together a new band of outlaws.

The reformed gang, with Doolin and Bill Dalton in charge, wasted no time getting back to robbing. On November 1, 1892, the Wild Bunch robbed the Ford County Bank at Servile, Kansas, getting away with all the cash on hand and over $1,500 in treasury notes. But they paid a price – shortly after the robbery. Oliver “Ol’” Yantis, one of the gang members, was recognized and gunned down by the Stillwater city marshal.

After marrying Edith Ellsworth on March 4, 1893, Doolin continued down the path of the lawless and robbed a train on June 10, 1893. During the raid, Doolin was shot in the leg. He recovered from his wounds and on January 29, 1894, the Doolin gang robbed a bank at Pawnee. This was followed by additional robberies at Woodward, Oklahoma (March 13, 1894) and Southwest City, Missouri (May 10, 1894). During the Southwest City raid, J. C. Seaborn, a former state senator was murdered.

Doolin and his gang continued their robbing, their largest haul being around $40,000 from an East Texas bank. But the gang’s days were numbered as more and more lawmen joined the chase. “The Three Guardsmen,” known as the three best lawmen of the time, included Chris Madsen, Heck Thomas and Bill Tilghman were on the heels of Doolin and the gang and never gave them a rest, hounding them through five states. Outlaw or not, Doolin was considered a fair man. This is the story Howard related to HPL that Doolin saved the life of Bill Tilghman by preventing Red Buck Weightman from shooting Tilghman in an ambush. Tilghman was well known for his honesty and fairness, using force only when necessary and had the respect of both lawmen and outlaws.

One morning, as Tilghman’s posse was closing in on Doolin, he and his boys were eating a hearty breakfast at a farmhouse – the farmer erroneously believed Doolin and the boys were posse members. Doolin stepped outside the farmhouse’s kitchen and spotted Tilghman and his posse approaching from a distance. Doolin then told the farmer that another posse would be showing up soon and they would be hungry too and would want breakfast and that they would pay for all of the meals, including theirs. Tilghman and the posse arrived and ate a large breakfast. The farmer then told Tilghman that “the other boys” said he would be paying for their meals too. Tilghman then reluctantly paid for not only his posse’s meal, but for the Doolin gang’s meals as well!

Tilghman finally caught up with Doolin in December of 1895 in a Eureka Springs, Arkansas bathhouse where Doolin had gone for treatment of a rheumatic leg he devloved as the result of being shot in the foot during a 1893 train robbery. Tilghman transported Doolin to the Guthrie, Oklahoma Territory prison without the aid of handcuffs or restraints. At the time of his arrest, Tilghman noticed Doolin had a small silver mug. Doolin told him the mug was a present for his infant son. Tilghman, being a man of kindness, saw to it that Doolin’s son got the mug. Six months later Doolin escaped with 13 other men, all ready to resume thier lives of crime. 

Doolin rode hard and fast to New Mexico and hid out at the ranch of writer Eugene Manlove Rhodes. But Doolin was lonely, missing his wife and child, and he was bound and determined to have them with him. He then rode back to Lawton, Oklahoma to retrieve his family. On the night of August 25, 1896, Doolin was approaching his father-in-law’s farmhouse, where his wife and child were staying. A posse, led by Heck Thomas, heard that Doolin was in the area so they were waiting for him. Doolin came up, on foot leading his horse and carrying his rifle, whistling as he walked in the moonlight. Thomas shouted from behind some bushes, ordering Doolin to surrender. Doolin raised his rifle, which was promptly shot out of his hands by the posse. He then pulled his pistol and fired twice before being killed instantly by a barrage of fire from Deputy Bill Dunn’s shotgun and from Thomas’ rifle. Mortally wounded, Doolin gasped out his last breath as he sank to his knees. As was customary in those days, Doolin’s dead body was publically displayed, shirtless, to show his fatal wounds.

Read Part II / Part III