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HENRY STARR

FROM HORSEBACK TO CADILLAC

He was a dapper, well-dressed gentleman who lived in Tulsa not far from the mayor and only a block or two from where the county sheriff lived.

Henry claimed to know them both, and he might have; after all, Tulsa had welcomed outlaws from its earliest days as a cow town, so long as they robbed banks, stages and trains elsewhere.

Henry Starr didn’t do the first automobile-powered robbery in American history, but he knew and admired the men who did. Oklahoma’s Poe-Hart gang invented the technique and used it for the first time on October 18, 1916, robbing the Isham Hardware store, where Coffeyville, Kansas residents had armed themselves to destroy the ill-fated Dalton gang twenty-four years before. But Henry arguably committed more bank robberies than anyone in the United States before his death at the beginning of the Roaring Twenties while trying to rob an Arkansas bank and get out of town in a car.

He had deep roots in Oklahoma, descending from James Starr, a Cherokee stalwart of the Treaty Party, which had advocated the peaceful removal of the party to Indian Territory in the 1830s. James was targeted for assassination after the Trail of Tears as a consequence. Although James survived the first efforts, his son Thomas Starr struck back against an innocent trader and his family near Dwight Mission in 1843. And after James Starr was at last assassinated, Thomas was instrumental in the killing of some thirty men whom he considered responsible before a tribal truce was called in 1846.

Henry’s own father, George, was a peaceful, honest man. That could not be said for their relation Sam Starr, whose father, Old Tom Starr, hosted the James-Younger gang and named his place on the Canadian River for Cole Younger. Sam married Belle Shirley, who described herself as the friend of any bold and courageous outlaw. Henry Starr always reminded people who asked him about Belle Starr that she was no blood relative of his.

He was born near Fort Gibson in 1873 and probably left home at age seventeen in 1890. Four years earlier, his father had died. Worse still, his mother promptly married one C.N. Walker, with whom he quarreled before leaving to work on a ranch near Nowata, Indian Territory, a few miles away. Henry had initiative, the kind that led him to supplement his cowboy income by bootlegging, then and there known as “introducing spirits into the [Indian] Territory.”

The judge in Fort Smith didn’t believe Henry’s claim that he’d borrowed the wagon and didn’t notice the booze. And he was less impressed several months later when young Henry was charged with horse theft. Now, “the Bearcat,” as Henry Starr came to be known, jumped bail and went on the dodge.

His first heist was not far from where he worked. Starr and persons unknown, suspected to be Ed Newcome and Jesse Jackson, robbed the Nowata Depot of some $1,700 in July 1892. The month after the Daltons met their Waterloo, Starr and Milo Creekmore robbed the Shufeldt Store at Lenapah, a burg south of Coffeyville, moving on to rob a store in Sequoyah later that November. These last two mercantile transactions netted Starr and Creekmore about $480, bringing Starr and his three partners to a grand total of some $57,000 today.

That was more than enough to attract the bloodhounds.

MURDER AT WOLF CREEK

Floyd A. Wilson had served as a sworn deputy U.S. marshal with legendary black lawman Bass Reeves nine years before, but he was with the Fort Smith, Arkansas police department that November when his old friend Henry C. Dickey approached him about serving on a posse. Dickey was a deputy U.S. marshal and Pacific Express Company detective at a time when that kind of dual employment was perfectly legal.

The next month, after Wilson was reappointed as a deputy, the pair set out for the Cherokee Nation, arriving at the Arthur M. Dodge “XU” Ranch some seven miles north of Nowata on Monday, December 12. They searched the immediate area for the fugitive, returned to the XU for dinner the next day, went into the ranch house and learned that Dodge had just spotted Henry riding toward nearby Wolf Creek. Wilson’s horse was saddled, but since Dickey’s was not, Wilson rode ahead after Dickey instructed him to arrest Starr if possible.

But by the time Dickey caught up with them, the shooting had commenced.

“Hold up, I have a warrant for you!” Wilson yelled at Starr, who had already reached the stream that might have protected him if he’d been a little faster. Instead, the fugitive dismounted, faced Wilson and yelled back just as the deputy rode toward him and jumped off the horse, firing over Starr’s head, intentionally or otherwise. Starr had a better day. He shot Wilson five times, placing the last one in the deputy’s chest, point blank.

That was about the time Dickey caught up, just in time to fire a few rounds without effect before Starr mounted the dead deputy’s horse and rode away toward the Osage Nation. Later, he recalled that he fled with “fear tugging at [his] heart and [his] brain afire.”

In the Osage, he hid out with Jackson and one Ed Newcomb near the Big Caney River, but they blundered into a combined force of some fifteen deputy U.S. marshals and Indian police on January 20, 1893, near Bartlesville. Still, they somehow managed to escape. Later that month, they rode seventy-six miles to Chouteau, where they robbed the railroad depot and a store and followed that with a raid on Inola nearby in early February. It was time for Starr’s first bank robbery.

Caney National Bank in the little Kansas town just north of the Indian Territory seemed like a prospect. Frank Cheney, a farmer who lived just north of Wagoner, followed Starr into the bank and walked directly into the vault. He helped himself to some $5,000 in coin and currency while Starr hustled the employees and customers into a back room.

Their next stop was Pryor Creek, Indian Territory, on May 2 for an evening robbery of the MK&T train. When they couldn’t get access to the safe, they robbed the more affluent-looking passengers of their cash. Later, Starr claimed that they relieved the passengers of $6,000 in cash, as well as a “consignment of unset diamonds.”

Their next target was the People’s Bank in Bentonville, Arkansas. The day before the job, Starr had scouted the prosperous little town, but on June 5, the five-man robbery team ran into some serious trouble.

“They’re holding up the bank!” a youngster shouted into the courthouse. After the alarm was sounded, gang member “Happy Jack” Cumplin dodged rifle fire from three or four men across the street as, inside the bank, Starr loaded up on silver, gold, currency and hostages. Later, as the gang and their captives left the bank, one brave woman reached out and pulled a hostage carrying the silver into a building. Despite the setback, the Starr crew still escaped with $11,000 and rode on to Cheney’s farm near Wagoner, Indian Territory, where they divided the money, made plans to reunite later and split up.

Kid Wilson, Henry Starr and Starr’s wife soon boarded a train at Emporia, Kansas, with plans to visit California, but during a layover in Colorado Springs, Colorado, Wilson and Starr were arrested and returned to Fort Smith.

Starr faced thirteen counts of highway robbery and a murder charge for killing Floyd Wilson in the court of Judge Isaac Parker. A jury found Starr guilty of all charges, but the murder conviction was reversed twice by the U.S. Supreme Court before Starr finally pleaded guilty to manslaughter and was sentenced, on January 15, 1998, to serve a combined sentence of fifteen years and seven days. He left for the federal prison at Columbus, Ohio, eight days later, with that old Bentonville bank job hanging over his head but an ace in his sleeve.

Only five years later, President Theodore Roosevelt reduced his fifteen-year sentence to time served and released him out of admiration for something Henry Starr had done in the Fort Smith lockup on the evening of July 26, 1895. Back then, Henry had convinced cold-blooded Crawford Goldsby, better known as “Cherokee Bill,” to hand over a pistol and surrender after killing guard Lawrence Keating during an escape attempt. Although Goldsby didn’t have much to lose that hot July evening, Starr had observed how gentle Bill was with his mother during a few visits. “Your mother wouldn’t want you to kill any more than you’ve already killed,” Starr told him. “Don’t make it any harder for her.” Goldsby surrendered and was hanged the next year.

And now, in 1903, when President Roosevelt released him, Henry moved to Tulsa, where his mother ran a restaurant. As the next five years went by, he got married, became a father and even took his young family to watch the inauguration of Oklahoma’s first governor in 1907. But there was trouble brewing in Bentonville.

The Arkansas authorities hadn’t forgotten about that 1893 Bentonville robbery. And Oklahoma governor C.N. Haskell had turned down extradition requests on technical grounds, but Starr didn’t know that. During the winter of 1907–08, he had teamed up with Kid Wilson in the Osage. They bought some rifles and headed north on Friday, March 13, 1908, to Tyro, Kansas, where they robbed the bank. Years later, Starr regretted that he’d gone wrong again because he “preferred a quiet and unostentatious interment in a respectable cemetery rather than a life on the Arkansas convict farm.”

From there, they moved west; robbed the bank in tiny Amity, Colorado, near the Kansas border of about $1,100; and dissolved the partnership. Kid Wilson was never heard from again, but Henry Starr eventually made his way to Bosque, Arizona, southwest of Phoenix. One year after the Amity bank job, he was arrested there, returned to Colorado, promptly convicted and sent to the state prison, where he wrote Thrilling Events: Life of Henry Starr . He was released on the condition that he would never leave Colorado and started his own restaurant near Amity, but within a year, he left the state with a merchant’s wife.

Career bank robber Henry Starr. Western History Collections, University of Oklahoma Libraries .

Perhaps it was only a coincidence that shortly after Henry Starr left Colorado, fourteen Oklahoma banks were robbed at two-week intervals beginning in September 1914 and ending the following January. Most of these daylight robberies were in the eastern counties, but five were in central Oklahoma. The money taken totaled over $31,000, about $722,000 today. A $15,000 reward ($1,000 for any single robbery) was appropriated by the legislature just before the cashier at the Carney State Bank, four days after Christmas, identified Henry Starr as the leader of the men who robbed him. A couple who fed the gang later that day also identified him.

The new Oklahoma governor, Robert L. Williams, promptly offered $1,000 for Starr dead or alive, but the Bearcat had made other plans, as he and the woman he’d brought back from near Amity, Colorado, lounged about his Tulsa home, not far from where the mayor lived and only a block or two from the county sheriff.

Much like Coffeyville, Kansas, Stroud, Oklahoma, had two banks. Henry Starr believed that he had a large enough crew to accommodate them both—on the same day—without being wiped out the way the Daltons were twenty-three years earlier. Starr masterminded the only successful two-for-one bank robbery in American history but ended up in the hoosegow while his accomplices enjoyed the loot.

The six-man Starr gang rode into Stroud on March 27, 1915, but immediately ran into trouble, even as a combined $5,800 in cash was being collected at the Stroud National and the competing First National Banks. During the gun battle that followed, Henry Starr and Lewis Estes were so badly wounded that they had to watch the rest of the gang escape. Later, Starr complimented Paul Curry, the seventeen-year-old who shot him, on his marksmanship.

The Oklahoma authorities weren’t as forgiving, but at least Starr owned up to his errors while serving the twenty-five-year sentence he received five months after being captured. After publicly repenting for his life of crime, he was pardoned a few months shy of his fifth year at the Oklahoma prison in McAlester.

He returned to Tulsa, married a third time, moved to nearby Claremore and was successful in the movie business for a time. We will never know whether he was broke or just bored, but on February 21, 1921, he drove into Harrison, Arkansas, with three companions and stopped in front of the People’s State Bank. The other bank robbers drove away without the $6,000 he had stuffed into his pocket because Henry couldn’t join them. While Starr was watching a cashier open a safe, the former bank president, age sixty, pulled out a rifle he’d long kept in the bank vault for a day like this and shot him in the right side. Starr hit the floor paralyzed and died two days later, after telling his attending doctors, “I’ve robbed more banks than any man in America.”

And quite possibly, he had.