Henry Starr, Oklahoma's King of Bank Robbers

Henry Starr1893 was a busy year for Henry Starr and his outlaw gang. In January and February, they robbed railroad depots and stores in the Indian Territory. In March Starr and Ed Newcomb (or Newcombe – both spellings appear in Kansas City newspapers) staged their first bank robbery, in Caney, southwestern Kansas. “Indian Ed” Newcomb may earlier have been in Butch Cassidy’s Wild Bunch; he had reportedly joined Starr in a train robbery in the Territory in November, 1892.

Since Starr was wanted for the murder of a Deputy Marshal in December, the Caney robbery was front page news in the Kansas City Journal, which described in detail (March 28, 1893, p.1) the two outlaws riding into the little town, tying their horses about 100 yards from the Caney valley bank, and with revolvers drawn locking bank employees in a back room before scooping up all the money in sight – about $2,000 – and riding off.

“It was accomplished so quickly and quietly,” the paper reported, “that the work was over before the citizens of the village were aware that anything was wrong.” The citizens immediately organized a posse to chase the gang, “but there is little probability of their capture.”

Starr, the Journal said, “is a bad man, but not so dangerous as were Bob and Emmet Dalton.” The Daltons were still in everyone’s mind, six months after their failed raid on Coffeyville, Kansas, when they had tried to outdo Jesse James’ gang by robbing two banks at once, in broad daylight. Two of the Dalton brothers and a confederate were killed in the attempt.

The Daltons, like the James-Younger gangs and other lesser known outlaw gangs in the last decades of the nineteenth century robbed banks, trains, depots, and stores for the money, of course, but their motives were often complicated by the politics and economics of their times: the Civil War for the James brothers, popular antipathy toward bank and railroad monopolies in the 1890s for the Daltons, and oppression of native Americans in the case of Henry Starr.

A further complication was the impulse of gang leaders to try to outdo each other and achieve greater notoriety in the press. As railroads and the telegraph knitted the country together and western state governments imposed order, the “Wild West” speedily vanished, surviving only in cartoonish Wild West shows, pulp fiction, and robber gangs who roamed less organized areas, like the Indian Territory, emerging periodically to descend on trains or small town banks. Attitudes toward outlaws in the popular press in 1893 were often ambivalent, since outlaws embodied manly freedom and challenge to the establishment.

The Times, (March 28, 1893, p. 1) for example, expressed admiration for the way Starr and Newcombe carried off the raid, describing it as “the coolest piece of outlawry yet reported,” and Starr himself as “the bold bandit.” The robbery, in the Times account – reprinted in the Mail (March 28, 1893, p. 1) without attribution to the Times – was “not only one of the most daring in the annals of crime on the border, but was at the same time one of the most unique…,” done so efficiently that apart from the people in the bank no one in town was aware it was going on. This was by implication a contrast to the bungled Coffeyville raid where the Dalton gang was greeted by armed townsmen as they emerged from the two banks.

The Times described the two robbers as a “half breed Indian known to be the outlaw Ed Newcomb, and a white man who was recognized as the notorious Henry Starr.” Henry Starr was actually also a “half breed” Cherokee, proud of his Cherokee blood and contemptuous of his step-father, a white man, and of the deputy marshals who first arrested him at age 16 for “introducing spirits into the territory.”

While in the bank, Starr and Newcomb joked with bank officials and patrons that “the Daltons were not all dead by a ---- of a sight, and that they were going to pay the bank across the way a visit,” connecting their robbery to the already almost mythical Dalton gang and its failed two-bank agenda. Starr and Newcomb marched their captives into a fenced yard behind the bank, locked the back door, walked out the front door, mounted their horses, and rode off toward the Indian Territory two miles away. Ten minutes elapsed before a posse could be organized and set out in pursuit: “the chase was exciting,” said the paper, “the pursued and the pursuers riding like the wind across the level prairie. The robbers were superbly mounted, and if they succeed in eluding the posse until night they will be safe.”

Muted admiration for Starr was even more apparent in newspaper reports on their next robbery, of a Missouri, Kansas and Texas Railroad passenger train in the Indian Territory in May. Six men, “supposed to be the notorious Henry Starr gang of robbers,” according to the Journal,  (May 3, 1893, p. 1) were involved in the well-planned raid, which greeted the incoming train at the Pryor Creek station.

Prior to the train’s arrival the gang bound and gagged the station agent. “When the train stopped the robbers covered the engineer, fireman, conductor and train crew with Winchesters and forced them to leave the train. They were marched off some distance and two men placed to guard them.” Failing to persuade the express car messenger, “with a Winchester at his head and a knife at his throat” to open the car safe, the robbers took “everything they could lay their hands on in the way of money and valuables” from the passengers, who included a “party of capitalists” from the East, among them the president and vice-president of another railroad. “Great excitement prevailed on the train and many ladies fainted,” said the paper, although no one was killed or injured.

The Star reported without qualification that the “Starr gang of robbers” was responsible – conjectural attributions of robberies to well-known gangs were commonplace in newspaper reports, often encouraged by the robbers themselves – but that the gang played a Robin Hood role: “They felt the people’s hands and some of those who had hardened hands, indicating severe toil, were not robbed.”

For the next month, rumors circulated about the location, intentions, and composition of the Starr gang. Early in May they were reported in the Star  to have ridden into Caney, Kansas, site of their March robbery, with criminal intentions. Finding the bank and stores closed against them, the townsmen having received warning, they retreated.

Later in the month, the Star reported that the gang, consisting this time of eight men, was seen near Caney, perhaps contemplating an attack on the Denver, Memphis & Atlantic train,” but no attack was made. Starr and two of his men were seen at their favorite haunt of Nowata, getting their horses shod, and Starr commented that “they would have to make another haul, as they were running short of money. It is reported that Bill Dalton is with them, but this is not generally believed, for he is thought not to have enough nerve.” 

The activities of Bill Dalton, the last Dalton brother on the loose, were a subject of constant rumor and speculation during the period. Dalton apparently enjoyed his notoriety, but may not have been responsible for most, if indeed any, of the several criminal activities attributed to him.

The Star story continues with other rumors: that “the outlaws were supplied with ammunition” from Coffeyville, and that there are 56 men in the gang, according to the brother of Starr’s girlfriend, “but this is considered mere boasting.”

Then in June five outlaws “believed to have been members of the Starr gang” robbed a bank in Bentonville, Arkansas, in a raid the Star compared to the “bold raid of the Dalton gang” on Coffeyville.  The story provides no reason for believing the men to be Starr gang members, nor did the raid have the efficient, speedy organization characteristic of Starr’s raids: the bumbling outlaws allowed one banker to escape carrying a bag of silver, and the operation took so long the townsmen rallied, wounding two outlaws as they fled. Speculative association with Starr and the Daltons, however, added interest to the story.

The association of the Bentonville robbery with Starr seems confirmed by a story the next week in the Journal (June 9, 1893, p. 8) that Henry Starr and his men were seen at the village of Oaks in the Indian Territory, “spending their money freely and drinking patent medicine. Much talk was indulged in,” says the paper, “and Starr told that he could have murdered all the Bentonville posse had he so desired.”

Starr is reported to have boasted that his men lay in ambush for the Bentonville sheriff and his posse, forcing them to surrender and return to town: “It is said that the sheriff took the bandit at his word and abandoned the chase, leaving the robbers to reach the Indian Territory in good time, and without receiving as much as a scratch.” 

The claims served to inflate Starr’s reputation, but his participation in the robbery remained in doubt, according to a Times story (June 13, 1893, p. 2) printed soon after. Regardless, Starr was being vigorously pursued by the law. The Times reported [from Nowata in Indian Territory that rewards totaling $15,000 – equivalent to roughly $350,000 in current dollars – were offered for him, dead or alive, although the amount was “questioned by some authorities.”

Eleven deputy U.S. marshals under U.S. deputy marshal Heck Bruner were in Nowata, scouting for Starr and company: “They are brave, determined, and experienced,” the paper said of Bruner’s men, “and every one remains a complete Heck Bruner and Ned Christie 1892arsenal.”  The year before, Bruner had been among those responsible for the killing of Ned Christie, a Cherokee leader accused – falsely as would eventually be revealed – of murdering a U.S. marshal.  Some of Bruner’s men slept in the loft of a livery barn previously owned by C.N. Walker, Henry Starr’s hated white stepfather. Walker and his wife, said the Times, “are excellent people and greatly esteemed. Those who know anything of the situation never connect them with any of Henry’s deeds or misdeeds.”

A couple of days later, the Times reported (June 15, 1893, p 2) that Bruner’s posse had surrounded the Starr gang in a wood twenty miles from Nowata, “and it is thought that the gang will be speedily captured…. Starr has been raised here and knows every hill and dale in the nation and can get a relay of horses whenever desired. It is now skill and bravery against the same in the opposition and the result is anxiously awaited.”

The next day’s report from the Times revealed (June 16, 1893, p. 1) that Starr’s gang had given the marshals the slip, if they were ever actually surrounded, and was at large “with all the freedom that even it could desire.” Horsemen, “splendidly mounted” and well armed, appeared in villages near Nowata, including Caney, Kansas, where citizens “at once proceeded to take a holiday, or at least to move about cautiously” when three men armed men rode into town and ordered meals at a restaurant. The time-lock of the Caney Valley bank was set and the bank closed for the remainder of the day. No attempt was made to capture the men, and Bruner’s sizeable posse was nowhere in evidence: “nothing has been heard from them since they were in the depths of the Dog creek timber.”

Two weeks later, Henry Starr was captured without a fight while eating at a restaurant in Colorado Springs, with StarrHenry Starr quoted in the Star as remarking “It is a good thing you got the drop on me or there would have been some corpses around here.” A gang member, Kid Wilson, and Starr’s wife, “about 18 years and rather prepossessing,” were also taken, along with money in greenbacks and $500 in gold. 

The Star rehearsed Starr’s career: his early career as a cattle thief in the Indian Territory, the “dash which he displayed in all his depredations” as he gathered a “band of desperadoes” around him and graduated from “highwayman” to “full fledged train robber”: 

His operations were bold, his movements were quick and he did not hesitate to take human life in beating his retreat to the many fastnesses and hiding places with which the country abounded. He knew every foot of the territory….. For years hundreds of deputy marshals have been looking for Starr and his gang and their instructions were to take them alive or dead, the latter preferred.

He was a sure shot and a tireless rider so that it was almost impossible to run him down. He rarely showed himself in the larger cities preferring the freedom of the country where his friends lived and where he was perfectly at home. He came from a family similar in many respects to the Daltons, there being hardly one member who was not imbued with murderous instincts and the love of outlawry. His latest exploit was the daylight raid on the bank at Bentonville, Ark., in which three citizens were shot. He is also credited with several recent train robberies in the Indian territory.

The story also mentions that Belle Starr, “the most dashing rider in the West and the most picturesque woman desperado chronicled by history… the equal of any of the men in running off a bunch of cattle or in stampeding a drove of horses” was a close relative.

The Star summary mixes fact with speculation and sensationalized rumor. There is no evidence, for example, that Starr killed anyone except deputy marshal Floyd Wilson during the 1892 shoot out. Some members of his family, including his mother and sister, were well-respected citizens, nor was Henry’s participation in the Bentonville robbery yet a certainty (though he would later give a detailed account seemingly confirming it while in the penitentiary at McAlester, Oklahoma. 

Whether or not he was at Bentonville, his most recent robbery, his last for 1893 as it turned out, was probably not there but at the railroad station in Chelsea in the Indian Territory, as the Mail reported, where “In broad daylight Starr walked into the station, and with his Winchester drawn, coolly forced the operator and agent to hand over all the money on hand, about $400.”

     Capture of the “notorious Cherokee bandit” was a sensational event. The Times (July 12, 1893, p. 1) offered a dramatized, melodramatic account describing the efforts of his mother and “pretty, black-eyed sister” Helen, to get Henry out on bond: “She caressed her mother in a tender way,” said the paper, “but her arms gave way midst bitter sobs. “So they have captured Henry, have they?” inquired a friend. “Yes, they say so; but he is not guilty of half what they charge him with,” answered the mother’s trembling voice.”  Helen Starr is quoted in the same story defending her brother: “Henry was never a bad boy, but some people try to make him out a terrible fellow. He killed a man, but the man was trying to kill him and he had to do something to protect himself.”

Helen Starr is described as “pretty and winsome and bears evidence of having been well-reared. She is one-quarter Cherokee and Zeke Starr, treasurer of the Cherokee nation, is her first cousin. Helen lives in Fort Gibson, where she is beloved and admired by all. Henry was reared within eight miles of Fort Gibson and is known by every inhabitant. The mother lives at Nowata and is highly respected, besides being well off.”

Even while Starr was being transported from Colorado to Arkansas for trial, a bank in Mound Valley, Kansas, near Coffeyville, was robbed by three men claiming to be members of his “band of desperadoes,” as the Times story (July 14, 1893, p. 1) put it, escaping with $800. “Guess you’ve heard o’ Starr, h’aint you?” one of the robbers is quoted as asking a cashier. “Well, Starr sed once that he hankered to do a little biz up in this section, but jest now he’s confined to his room…. We need this stuff to get Henry Starr out, and we’re going to get him out.”

John KloehrHe promised not to rob the cashier since “You can’t stand it as well as Condon, who owns the bank,” the Mound Valley bank being owned by C.M. Condon, who also owned the Coffeyville bank unsuccessfully robbed by the Daltons.

The “garrulous bandit” had thus connected himself to Starr’s gang and the Daltons’, as well as to the popular prejudice against bankers, assuring front page stories on what the Times called “an unusually bold” robbery. The connections continued, since the posse sent out to intercept the Mound Valley robbers was headed by John Kloehr, credited with killing two of the Dalton brothers in the Coffeyville raid.

On July 15, Henry Starr and Kid Wilson came through Kansas City in custody, on their way from Colorado to Fort Smith, Arkansas. They were, reported the Star, in “a bad frame of mind during the hour they sat in the depot waiting room…” A crowd of onlookers gathered around to stare at them; Starr cursed them, said the paper, and “spat in one man’s face and said he would make the whole crowd run if his hands were only loose.”  According to the Journal report, (July 15, 1893, p. 3) the man “retaliated with a good right hander on the bandit’s nose. Mr. Starr countered with some very choice epithets.”

The Times sent a reporter to interview Starr, (July 15, 1893, p. 1) without much success. “I’ve got no use for rubber-necked newspaper reporters,” Starr told him, “nor for anybody else in Kansas City; so take a sneak and don’t weary me.” The reporter countered with a question that was still open: “Mr. Starr, were you ever at Bentonville?” Starr gave a “wicked scowl, an oath hissed from between his clenched teeth,” and made a threatening move toward the reporter that ended the interview: “even desperadoes,” he wrote, “have rights which an inquisitive public is bound to respect.”

Studying Starr from a safe distance, he described him as looking to be “not over 23” – he was in fact probably 19 – “nearly six feet tall and rather lank looking….. His face is dark, his cheek bones high and his hair raven black. But his eyes are the distinguishing features of his whole make up. They are large and full and black as jet, with an evil look in them that can not be described,” the reporter wrote, before going on to describe Starr’s look: “a pair of eyes that sparkle with a sinister light and seem to look through one at a glance. Starr’s eyes are never at rest. All the while that he sat in the hotel office those ferret-like eyes were continually shifting from one object and face to another, and the look of hate never left them.” Even while boarding the train to Arkansas, Starr “kept cursing the crowd and Kansas City and everything connected with ‘the bloody town’.”

In October, at Fort Smith, Starr came before Judge Isaac Parker, the “Hanging Judge.”  A government witness testified (Kansas City Times, October 20, 1893, p. 4) that he had seen Starr go up to the wounded deputy and shoot him, undermining Starr’s claim of self-defense.  He was charged with thirteen counts of highway robbery and one of murder, found guilty and sentenced to hang. The U.S. Supreme court overturned Parker’s ruling and Henry was eventually convicted of manslaughter and train robbery and sentenced to 15 years in federal prison.

Even as Starr was awaiting trial in Arkansas, members of a reputed “Dalton-Starr gang” were reported in the Star  to be preparing a raid on banks in Arkansas City to take advantage of the great Oklahoma land rush scheduled for September 15. “The bandits’ plan,” said the paper, “is said to be to rob the banks after the rush, relying on the departure of nearly all the men. Nearly every officer on the police force is going to make the run, and the city will be almost wholly without police protection.”

Apparently no such raid  was attempted, but the great land rush of 1893 was a sign of the imminent end of the relative freedom and lawlessness of the Indian Territories, as in another sense was the jailing of Henry Starr.

But 1893 did not see the end of Starr's outlaw career. He spent only ten years in federal prison, earning early release by disarming a fellow prisoner, Cherokee Bill, and appreciation of his display of courage from President Roosevelt, who granted him a pardon. Soon he was back to robbing banks in Kansas and Colorado. Arrested again in Colorado and sentenced to a term in the Colorado state prison, he wrote his autobiography, Thrilling Events, Life of Henry Starr. in prison. Paroled again on a shortened sentence, he carried out a series of daylight bank robberies – fourteen are attributed to him between September, 1914 and January 1915 -- in Oklahoma.

The lure of that holy grail of bank robbers, the double robbery, which had brought down the Daltons over two decades earlier, remained before Starr and in March, 1915, he and six confederates tried to rob two banks at once in Stroud, Oklahoma. The raid lacked Henry’s usual timing and citizens were able to arm themselves. Henry and another outlaw were wounded and captured although the rest of the gang escaped, making the Stroud raid the first successful double robbery.

Sentenced to 25 years in the Oklahoma State Penitentiary, Starr became a spokesman for the honest life: “I’m 45 yearsDebtor to Law poster old now,” he is quoted as telling a reporter. “And 17 of my 45 years have been spent ‘inside.’ Isn’t that enough to tell any boy that there’s nothing to the kind of life I have led?” His 25 year sentence reduced to four, Henry was released in 1919, returning to the straight and narrow and even producing and starring in a film, A Debtor to the Law, about the Stroud robbery.

In February, 1921, Starr drove in an automobile into Harrison, Arkansas, with three companions, to rob the People’s State Bank.  During the attempt, Henry was shot in the back. Even while dying, he boasted to doctors, “I’ve robbed more banks than any man in America.”

Writes one admiring commentator about Henry’s life:

Henry died as he had lived, in a violent manner, but true to the code of the outlaws, he never revealed a single partner in any crime.  He never shot anyone in the commission of a crime, and served his time in jail like a man. He had succeeded where others had failed by robbing two banks at once, and by robbing more banks than anyone else.

During his 32 years in crime, he claimed to have robbed more banks than both the James-Younger Gang and the Doolin-Dalton Gang put together. He started robbing banks on horseback in 1893 and ended up robbing his last in a car in 1921. Allegedly, he robbed 21 banks during his outlaw career making off with nearly $60,000.00.


 August 16, 2013