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But his time with the famous outlaws was short-lived.

Within weeks of a train robbery at a spot called Rocky Cut, near Otterville, Missouri, James-Younger Gang member Hobbs Kerry was behind bars. The 23-year-old outlaw was arrested in southwest Missouri for his role in that July 7, 1876, holdup and taken back to the central part of the state, where on August 4 he implicated the other members of the notorious gang.

Many authors have portrayed Kerry as a raw recruit whose youth and inexperience led to his quick capture and eager confession. But Kerry’s background suggests he was more reckless than naive.

The son of an English-born schoolteacher, Kerry moved with his family from Arkansas to the rowdy lead-mining camp of Granby, Mo., in the late 1850s when he was a small child. He and his older brothers, Albert and Toby, grew up among the rough characters of the booming camp and became miners during their youth. (Previous authors have spelled Kerry’s name with a K, and that spelling has been accepted for the purposes of this article. However, evidence suggests the actual spelling was “Carey.”)

On July 15, 1870, a man named Bennett killed Toby Kerry during a row over a card game at a “cyprian camp” near Granby. The Kerry brothers evidently had a predilection for sporting ladies, because a year later Albert Kerry killed a man in Granby in a dispute involving a prostitute. The Neosho Times said “a slippery cyprian named Mollie Howard” was the cause of the difficulty that led Albert Kerry to shoot J.S. Dunlap on July 4, 1871.

Apparently, no charges were filed, and in October 1873, when Granby was fully organized as a town, Albert Kerry was made city marshal. However, his role as primary peacekeeper was not enough to deflect suspicion two months later when a man named John Cole was found shot dead outside a Granby saloon. Albert, Hobbs and a third man were arrested and charged with the December 6 murder, though they were released shortly afterward for lack of evidence.

In late 1875, Hobbs Kerry left Granby for the livelier mining town of Joplin, 20 miles northwest, where he met Bruce Younger, half-uncle to Cole Younger and his brothers. He also got to know Bill Stiles (alias Bill Chadwell) and Sam Wells (alias Charlie Pitts), whose father had been a neighbor of the Younger family in Lee’s Summit. Bruce said Cole and Bob Younger had recently visited him in Joplin, and Kerry and his three new friends kicked around the idea of recruiting Bruce’s infamous kinfolk to help them hold up the bank in Granby.

After spending the winter in Joplin, the four men crossed the state line into Kansas in late spring 1876 and took jobs in the coal mines near Scammon. Tiring of the hard work, Bruce Younger soon left his companions, pulling out of the scheme to rob the Granby bank. Meanwhile, Chadwell traveled to central Missouri to recruit the Younger brothers for the job. He soon reported back to Pitts and Kerry that the brothers were on their way.

When they had not arrived a week later, though, Kerry, Pitts and Chadwell grew impatient and in late June started north to link up with the famous outlaws. Failing to locate the Youngers at their stomping grounds around Monegaw Springs, Mo., the three rode on to Jackson County, where they ran into Frank James. James guided them to Dick Tyler’s house in another part of the county. There, they met up with Cole and Bob Younger, Jesse James and Clell Miller.

The outlaws divided into two groups and rode east, reuniting at California on July 4. Two days later they started back west in pairs and once again reunited on July 7, about two miles east of the Missouri Pacific Railroad bridge crossing of the Lamine River east of Otterville. Near sundown, six members of the gang went down to the bridge and took the watchman captive while, according to Kerry, he and Chadwell stayed behind at the rendezvous point. At 10:30 that night at Rocky Cut, the same six outlaws forced the watchman to flag down a train bound from Kansas City to St. Louis while Kerry and Chad well served as lookouts. Just to be sure, the outlaws had placed ties on the track to stop the train, and when it came to a halt, they fired off their six-shooters, quickly boarded the train and took an estimated $15,000 from the express safes.

Following the robbery, the gang rode south through the night and stopped on the morning of July 8 seventeen miles southeast of Sedalia, where they divided the loot. Kerry’s share was about $1,200. Afterward, the gang split up, with Pitts, Chadwell and Kerry riding together. On the morning of July 9, Kerry left his two partners and took a train from Montrose to Fort Scott, Kan. That evening he went on to Parsons, and the next morning he took a train to Granby by way of Vinita in Indian Territory. During the next three weeks, Kerry divided his time between Granby and Joplin, where he reunited with Bruce Younger. He also managed a brief trip to Indian Territory to see his brother Albert.

Back in June, before the plot to rob the Granby bank fell through, St. Louis detectives had gotten wind of the scheme and made a trip to the area to investigate. Suspecting that some of the same men who’d planned the Granby job were involved in the train robbery, the lawmen returned to southwest Missouri after the Otterville caper. Upon learning that Kerry had also returned after an absence and had been flashing around money, they arrested him in Granby on July 31 on suspicion and took him back to St. Louis. (A week later Bruce Younger was also arrested but soon released.)

Kerry, who had just $20 on him when arrested, was transferred to Sedalia, where he gave his August 4 statement that implicated his partners in crime. Next, he was sent to Boonville to await trial. Due in part, no doubt, to his cooperation with authorities, Kerry was sentenced to only four years in prison.

Meanwhile, a plot was already afoot among the remaining gang members to make what Cole Younger called one last haul. Shortly after Kerry’s confession, a letter appeared in The Kansas City Times, purportedly from Jesse James, denouncing Kerry as a “notorious liar and poltroon,” but Kerry’s statement was generally accepted and may have prompted the gang to hasten their plans. By late August, the same seven men who had robbed the Otterville train, plus Jim Younger in place of the jailed Kerry, were heading north toward Northfield, Minn., and a date with destiny. On September 7, 1876, Bill Chadwell and Clell Miller were killed during the ill-fated robbery of that town’s First National Bank, and two weeks later Charlie Pitts was killed and the Younger brothers captured by a posse. Only the James brothers escaped to carry on their outlaw careers. What happened to Hobbs Kerry upon his release from prison remains a mystery.


Originally published in the October 2008 issue of Wild West. To subscribe, click here