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Henry Starr

Oklahoma Historical Society Archive
Taken outside the jail at Chandler, Oklahoma, where he was being held.

Last of the Horsebackers

Though perhaps not justified, I have always entertained a sentimental regard for Henry Starr. To me, he is the classic example of the man lost to outlawry who should have been saved for something better. He had the intelligence and personal charm to have taken him a long way.

I do not agree with those who say he was pushed into outlawry. True enough, he was unjustly accused of stealing a horse when he was barely eighteen, arrested by the Cherokee Indian police and taken to Nowata, where he suffered the humiliation of being led into the hotel dining room with his hands in irons and being chained to his bed that night. The charge was dropped before he came to trial, but eight months later he was arrested a second time on a similar charge. There appeared to be no evidence against him. He was held for trial, however, his cousin Kale Starr and J. C. Harris, a tribal chief, going bond for him.

The old Starr-Ross feud was still very much alive. Sam Starr, the patriarch of the Starr clan, had returned to his old bailiwick after serving a long sentence at the Southern Illinois Penitentiary, at Menard, for introducing and selling whisky in the Territory. The difficulties young Starr was having may well have been the work of the Ross faction. Apparently convinced that, innocent or not, he was about to be railroaded into prison, he jumped bail. When he failed to appear for his trial, the bond was forfeited and Harris and Kale Starr offered a reward for his capture. But he was already on the scout. He eluded the Indian police without difficulty and in the wilds of the Verdigris Valley met up with Bill Cook, Cherokee Bill and the Verdigris Kid, the charter members of the Bill Cook Gang, which was then being formed. Later, he was to join them and continue his self-propelled progress into outlawry.

Henry Starr is described by some as being all-Indian and by others as more white than red. The truth is that the only white blood he inherited from his father, Hop Starr, was the ScotchIrish strain that had been in all the Starrs since their early contact with white men in their original homeland in the Carolinas and Georgia. His mother was a quarter-blood Cherokee. In appearance he was typically Indian, with his straight black hair, black eyes, aquiline nose and swarthy skin. Though he was a slight man, under six feet tall, he had the physique of an athlete, and, says MacDonald in Hands Up!, "moved with an aboriginal grace, could dog-trot for half a day, had the Indian instinct for finding his way, and could live on roots, berries and nuts and sleep on the ground for months at a time, if need be."

He was born at Fort Gibson on December 2, 1873, and attended the Indian school at Tahlequah. He was remarkably abstemious, never using liquor, tobacco, tea or coffee. He made friends easily, many of whom remained loyal to him after he was steeped in banditry. Everybody seems to have liked handsome, soft-spoken Henry Starr. The U.S. marshals, whose business it was to run him down, respected him, even befriended him at times. They knew he was "absolutely without fear, that he would fight like a wildcat if cornered."

Nothing infuriated him so much as to read in the trash that was written about him that he was the son of Belle Starr. She was his cousin, and only by marriage, his father and Sam Starr, Belle's husband, being brothers. He claimed he had never been acquainted with her, which may be true, for he was not yet sixteen when Belle was killed.

Though Henry Starr robbed a score of banks and faced the gunfire of marshals and irate citizens many times, it is a tribute to his coolness when the chips were down that only one killing appears on his record, and that occurred a few weeks after he jumped bail on the horse-stealing charge and was hiding out in the Verdigris Valley. Whether you believe Starr's version of what happened, or accept the testimony of two eyewitnesses, it was one of the strangest pistol duels ever recorded.

It took place on the Albert Dodge ranch, near Nowata. Starr was then nineteen. He had worked as a cowboy for Dodge the previous year, and it was at the Dodge ranch that he was arrested on the first horse-stealing charge and again on the second. When a store at Lenapah and the express office at Nowata were robbed, suspicion grew that it was the work of the fugitive Henry Starr. Floyd Wilson, a Parker deputy marshal, and H.E. Dickey, an express-company detective, rode to the Dodge ranch hoping they might find young Starr there. Dodge informed thern that he had not seen their man in weeks and did not expect to see him.

And now the incredible occurred, for as they were in the house drinking coffee, a rider came up, glanced in through the window, saw there were strangers present, and rode on. Later, under oath, Dodge said: "I told them [Wilson and Dickey], `There's the man you're looking for.'"

Wilson ran out of the house, leaped on a saddled horse and pursued Starr. A hundred yards away, the latter suddenly pulled up and dismounted. Wilson did the same when he came up to him, and Dodge and Dickey, back at the house, saw them confronting each other, not thirty feet apart, with pistols drawn. Wilson then fired a shot - "a warning shot, over Starr's head," said Dodge and Dickey. "Starr shot then; Wilson went down. Starr walked up to him and fired again, killing Wilson."

That was not the way Henry Starr told it. "When Wilson called on me to surrender I called back, `You can't take me, Wilson; go away.' `Throw away that gun and put up your hands or I'll kill you,' he replied. He probably thought I was only a kid and was afraid of him. I didn't want to kill him. 'All right,' I told him. `I'll lower my gun and give you a chance to shoot first and you better make a clean job of it. If I kill you it will be in self-defense. Shoot!' Wilson took cool aim at me, fired, and the ball sang past my ear. Then I put a bullet through his heart, mounted my horse and rode away." That was the story he eventually told a jury. They refused to believe him.

Slaying an officer was serious business, no matter what the circumstances. He would have an army of deputy marshals on his trail now. If captured, if would very likely mean that he would end up on the gallows at Fort Smith. No further persuasion was needed to send him scurrying off to join the Cook Gang.

He took part in at least three robberies with them. When winter put a temporary stop to their activities, he pulled away and began organizing his own gang. The men with whom he surrounded himself were older than he, two of them not inexperienced in the bandit business. They were Link Cumplin, Frank Cheney, Bud Tyler, Hank Watt, Kid Wilson and a character known only as Happy Jack. They were not "all cowboys," as one writer labels them; outside of Link Cumplin and Frank Cheney, the rest were cowboys only by adoption, range renegades who lived without visible means of support, not to be compared with the men Bill Doolin had recruited on the H X Bar.

At half-past two on the afternoon of June 5, 1893, Starr led them into Bentonville, Arkansas (about twenty-five miles beyond the Indian Territory line and about the same distance due west of Eureka Springs, where Tilghman had captured Bill Doolin), to rob the People's Bank. With the attention to detail that became his trademark, he had cased the town and the bank for several days. Each man knew what his position was to be when he reached his destination, and the route he was to take in making his getaway after the robbery.

Starr and Frank Cheney drove into town in a buggy, in which the gang's rifles were hidden. Tethered at the tailgate of the rig were two riding horses. Strung out some distance behind them so as not to attract attention, rode the others. Bentonville went about its business, unsuspicious of what was about to happen. The bank stood on a corner. The bandits came up at the rear of the building. On Happy Jack fell the assignment of holding the seven mounts. The rifles were snatched out of the buggy. Bud Tyler and Hank Watt took their posts halfway between the horses and the bank corner. Link Cumplin, the trustiest man of the lot, stopped at the bank door, the position of greatest danger. Starr, Cheney and Kid Wilson, a young Indian, pushed on inside.

Cheney and Kid Wilson leaped over the counter as Starr lined up the six men who were in the bank and made them stand against the wall, intending to use them as a screen when Cheney, Wilson and he marched out. Cheney went into the vault. Wilson scooped up the money on the counter.

Years later, while he was a prisoner in the penitentiary at McAlester, Starr described those few minutes. "Scores of people saw us enter and knew us for bandits. Shooting began the moment we entered the bank. I heard the shots, slap, bang, at Link, who was walking up and down in front, shooting at every head that showed. Every second of time now might mean the difference between life or death for each man of us. ... It seemed to me we were an hour in that bank, but it couldn't have been more than a minute or two before Cheney and Wilson sprang over the counter with the money in a sack. I told the six men I had lined up to do exactly as I said and they wouldn't get hurt. We started out behind them, but when we reached the street, fifteen or twenty men were shooting at us; it was as dangerous to stay with us as it was to run, and those six men just melted like snowflakes in a puddle. Link was shot almost to rags-one eye shot out-an arm shot through in two places, but he had his six-shooter in his good hand and was still blazing away. I helped him to his horse, and we tore out of town, all seven of us, not a man lost. A big posse chased us, but I never did think that posse tried very hard to get within gunshot distance of us."

There was only $11,000 in the grain sack; divided seven ways, it meant little more than $1,500 apiece. "Trifling pay," as Starr said, "for such a desperate venture." Of the six men who accompanied Starr on the Bentonville raid, none was to "ride" with him again. Link Cumplin went to Alaska and was killed in holding up an express messenger; Happy Jack was killed several months later by marshals in Indian Territory; Frank Cheney fell before their guns within the year; Hank Watt was shot down by a posse who caught him with stolen horses in his possession. Kid Wilson wound up in the penitentiary and, after being pardoned, went back to banditry and was killed. Of the six, only Bud Tyler died in bed.

With his share of the Bentonville loot, Starr married a girl named Mary Jones, a Cherokee mixblood, and took her to Colorado Springs. Kid Wilson accompanied them. There on July 3, less than a month after the Bentonville robbery, William Feurstine, a Fort Smith businessman, saw Starr on the street and notified the police, who discovered that Starr and his wife, registered under the name of Frank and Mary Jackson, and Kid Wilson, alias Frank Wilson, were staying at the Spaulding House. When Starr and his wife were taken into custody, between $1,800 and $2,000 was found hidden under Mrs. Starr's pillow. Kid Wilson was traced to a bawdyhouse and captured in the room of one of the inmates.

He and Starr were hustled back to Fort Smith. Wilson was sent up for fifteen years for armed robbery. Henry Starr faced a number of indictments, one of them for the slaying of Deputy Marshal Floyd Wilson. It was on the murder charge that prosecutor Clayton brought him to trial.

It was the only time he faced the famous Hanging Judge. He was convicted and sentenced to die on the gallows. It will be recalled how he dumbfounded Parker by breaking in on the longwinded haranaue the latter was pronouncing before passing sentence.

The date set for Starr's execution was February 20, 1895. He was still very much alive when the day passed. His lawyer had appealed to the Supreme Court, which then was possible, to set aside the verdict on the ground that the trial had been conducted in a manner prejudicial to the defendant. As usual on such appeals, months dragged by before that august body rendered its decision. In the meantime, Henry Starr remained caged in the overcrowded, vermin-infested hell-hole that was the Fort Smith court's prison. He was still there on the evening of July 26, when Cherokee Bill killed Turnkey Eoff and set off the riot. For his bravery in going into Cherokee Bill's cell and disarming him, the charge against him was reduced to manslaughter, and he was sentenced to fifteen years in the Ohio State Penitentiary.

At Columbus, with fifteen years of confinement ahead of him, he began the self-education that he was to pursue for the rest of his life. In his thirst for learning, his reading took him into widely unrelated fields-political science, ancient history, criminology and the science of firearms, phases of the last, such as the velocity of discharged missiles, windage and trajectory, requiring some knowledge of mathematics to be understandable. If he was an outlaw at heart, and the record says he was, he also had the instincts of a gentleman. He must have been a model prisoner. When he had served five years, the warden was convinced that Starr could safely be returned to society. He instituted proceedings for his pardon. President Theodore Roosevelt granted it.

On his return to the Territory, Starr found his wife and embarked in the real estate and insurance business in Tulsa. He was moderately successful. His son was born, and he named him Roosevelt for the man who had pardoned him. For five years he led a law-abiding existence, and then, when it appeared that he was a brand that had been saved from the burning, Oklahoma achieved statehood on November 16, 1907. It changed the course of his life and sent him careening back into outlawry.

Following the Bentonville robbery, Arkansas authorities had indicted him for armed robbery. All the time he was in prison, and afterward, fourteen years, they had kept it alive. But Tulsa was in Indian Territory, and they could not touch him. With statehood, he could be extradited, and they asked for it at once. Before going into hiding in the Osage Hills, he sent a friend to Guthrie (it remained the capital until 1910) to plead his case with Governor Haskell. "He was to tell him how I had been going straight for five years, and beg him not to let the Arkansas wolves get me. I did not know what the governor might do, but I was determined not to go to Arkansas, for there I would have been sent up for life. "I stayed in hiding. Within a month several banks were robbed in Oklahoma. [This is a quote from Hands Up!] I had nothing to do with them, but the newspapers printed scare-head stories that I had got off the reservation again, with forty kinds of war paint on. One day the telephone rang and the message I got from Guthrie was `He's granted it.' Well, what could I do? I had the name of robbing banks. I might as well have the game. So I decided to touch up a bank or two to get enough money to leave the country. I did that - and started for California on horseback."

On the way, he passed through the little town of Amity, Colorado, on the Arkansas River. Its one bank, patronized almost exclusively by farmers, looked so easy to rob that, in his words, it seemed a shame to pass it up. He collected several thousand dollars and continued on his way, but was captured by a sheriff's posse east of Lamar and sent to the Canon City penitentiary for twenty-five years. It was only then that he learned that Governor Haskell had not granted extradition on him; that he had misunderstood his friend, who had said, "He hasn't granted it," not "He has granted it." Of course, the truth came too late to save him.

This tale has withstood the test of time. When I first heard it many years ago, I was skeptical of it. In a way, I still am. I know there was a misunderstanding over the telephone message Starr received, but I doubt that it hinged on mistaking "has" for "hasn't." A conversation, however brief, would have corrected that error. I believe that Starr heard the man correctly and that the latter, in his haste to get word to him, had jumped the gun and was relaying information he did not actually have.

At Canon City, Henry Starr was once more an exemplary prisoner. He was made a trusty and put in charge of a road gang of a hundred convicts. At the end of the prescribed five years, the warden signed his application for parole. It was granted, with the proviso that he was to report to the parole board once a month and was not to leave the state of Colorado. He was no sooner at liberty than he hurried back to Tulsa to find his wife. He discovered that she had divorced him.

It was at this time that a wealthy stockman, who still had faith in him and believed he could get straightened out if he got away from his Oklahoma environment, took him up to St. Louis, bought him expensive raiment and got him a job. All went well for a time, until Starr was invited to a party in Webster Groves, a suburb. By chance, he got off the trolley car in front of the bank. Once again it was a case of a bank looking easy to rob. A week or so later it was held up by a lone bandit in typical border fashion. Starr disappeared from St. Louis.

He was next heard from in Oklahoma. In the course of the two years that followed, a score of small banks were robbed, all daylight jobs, and always by a lone bandit. The cry went up that Henry Starr was responsible, and it became so insistent that the legislature posted a reward of a thousand dollars for his capture, dead or alive.

At Stroud, Oklahoma, a little town on the Frisco Railroad, a few miles east of Chandler, the county seat of Lincoln County, on March 27, 1915, its two banks were robbed in spectacular fashion, the twin robberies being accomplished in less than a quarter of an hour. In some ways it was a repetition of the feat that had ended so disastrously for the Daltons at Coffeyville. The Stroud extravaganza was, eventually, to prove almost as costly to its participants.

At noon of that cold, blustery March day, Henry Starr jogged into Stroud with five armed companions whom he had recruited in the Verdigris Valley and the Osage Hills, the breeding ground of outlaws and horse thieves for half a century. They were "unknowns" in the world of banditry at the time: Lewis Estes, Bud Maxfield, Claude Sawyer and Al Spencer, an undersized young punk who survived to become one of the F.B.I's most wanted Public Enemies in the era of "automobiles and automatics" that was soon to follow. Very likely the fifth man who rode into Stroud that day was Spencer's brother-in-law, Grover Durrell, a future Spencer mobster.

Starr had cased the town carefully and knew that the local marshal went home to dinner promptly at noon, as did some of the employees of the banks. He had rehearsed the twin robberies with his men, and when they turned into the hitch-rack in front of a store less than half a block from the two banks, it was according to the prearranged plan. The reins of the six horses were turned over to Bud Maxfield. As he stood there alert, watchful, the others started up the plank sidewalk.

When they reached the first bank, Starr, Estes and Sawyer entered. The other two stopped at the door and fired a salvo of shots to clear the street and intimidate the townspeople. Across the way from where he was holding the horses, Maxfield saw a boy run into the butcher shop. He should have stopped him.

The robbing of the first bank was accomplished without difficulty. Starr and his two companions came out, and all five then crossed street to the other bank. When their business there was finished, they began retreating down the middle of the street to their horses, Starr bringing up the rear, walking backwards and holding the town at bay.

Stroud was stunned. Several hundred people saw them, knew they were bandits and that they had just looted both banks; but no one did anything about stopping them from getting away. Paul Curry, the boy of sixteen who had darted into the butcher shop when the looting began, picked up an old, sawed-off single-shot rifle, used for killing hogs, that stood in a corner behind the counter, and as the bandits passed the shop he ran to the door and fired at them. The heavy slug shattered Starr's hip. He collapsed, temporarily paralyzed from the waist down. The others turned back to help him. "I'm done for boys," he is reported to have told them. "Save yourselves." They left him lying there on the frozen street, and with them went the rnoneybag.

Thousands of bullets had been fired at Henry Starr. His clothing often had been punctured, but no bullet had ever struck him until now. He had no sooner been picked up and carried to the town jail than the cry of "Lynch him!" was raised by men who had been docile enough a few minutes earlier. The town marshal telephoned Oklahoma City for help. Tilghman responded. He was in Stroud three hours later, and his presence put an end to the lynch talk. Nevertheless, he removed Starr to the county jail at Chandler.

They were friendly enemies of long-standing. "Henry, I'm becoming convinced that you are going to live and die a criminal," Tilghman recalled having told him. "You've broken every promise you ever made me. You told me you were through robbing banks, and here I find you pulling a doubleheader." "Mr. Tilghman," he said, "when I came to Stroud to look things over, I saw it was just as easy to rob two banks as one, so I decided to kill two birds with one stone."

A posse led by Tilghman surprised Starr's accomplices a few days later, and in the fight that followed, Lewis Estes was killed and Bud Maxfield and Claude Sawyer were captured. Spencer and his brother-in-law (presuming it was he) escaped and made off with the loot.

When Starr was able to stand trial, he was found guilty and was sentenced to twenty-five years at McAlester. Maxfield and Sawyer went along with him. McAlester was reputed to be a tough prison, but Starr had no trouble there. He behaved himself and soon was given many privileges. Friends on the outside worked for his release. He appeared to be contrite. He was forty-seven, his health broken. In December 1920, he was released on parole, having served only five years and six months. In all, he had been sentenced to sixty-five years in prison, but he served only slightly more than fifteen. (During one period of freedom Starr produced and acted in a western movie filmed in Oklahoma.)

He returned to Tulsa but had no luck finding a job. He went on to Oklahoma City and sought employment in some minor capacity with the state. His reputation was against him. Oklahoma was booming, and he was a relic of the past who had outlived his time. Automobiles were everywhere, and hard-surfaced roads were shooting out across the prairies in every direction. Oil was making millionaires of dirt farmers almost overnight.

Henry Starr was no longer the handsome figure he once had been. He walked with a limp, stoop-shouldered and old beyond his years. Suddenly he disappeared and dropped from sight for weeks. And then on February 18, 1921, he was back in the headlines. Accompanied by two armed men, he walked into the bank at Harrison, Arkansas, a hundred miles east of Bentonville, where he had cracked his first bank, and informed William J. Myers, the cashier, and a bookkeeper that it was a holdup.

Myers was prepared for just an emergency. When Starr ordered him and his bookkeeper to back into the vault, he consented readily enough, for just inside the vault door he had a double-barreled shotgun loaded with buckshot. It was the bandit's intention to loot the vault and lock the two men inside while he and his confederates made their getaway. But as he followed Myers into the vault, the shotgun roared and Starr Crumpled to the floor. The two men he had with him, identity unknown, turned and fled.

Henry Starr, who had been among the first, and certainly was the last, of the noted horseback outlaws was dead. Waiting in the wings, ready to take over, was a new crop of bandits of a deadlier breed, mad dogs who killed without compunction. Armed with automatics, submachine guns and bombs, using speeding automobiles to make their get aways, they were to terrorize the country as the James-Youngers, the Daltons, the Doolins and the Henry Starrs never had.

Starr ("The Bearcat") died without a dollar, but he was not buried in a pauper's grave. In his flush days in Tulsa he had arranged with a local undertaker for his burial. "Someday," he told him, "you'll read in the paper that Henry Starr has been killed. When you do, give me a decent burial." The compact was fulfilled. Starr's body was brought to Tulsa and given a Christian funeral and burial. It was the end of the era of the outlaw on horseback.

Harry Sinclair Drago. Outlaws on Horseback: The History of the Organized Bands of Bank and Train Robbers Who Terrorized the Prairie Towns of Missouri, Kansas, Indian Territory, and Oklahoma for Half a Century. Bramhall House, New York, 1964.

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