JJ Webb

John Joshua Webb: Lawman, Gunfighter, Outlaw
John Joshua Webb stands as one of the most fascinating and contradictory figures of the American Old West, a man who transitioned from frontier lawman to notorious outlaw in a single turbulent decade.
Born on February 13, 1847, in Keokuk County, Iowa, Webb was the sixth of ten children born to William Webb Jr. and Innocent Blue Webb. His childhood was shaped by constant movement, driven by his father’s restless wanderlust. The family relocated frequently, eventually settling in Illinois during the 1860s before pioneering again in Keokuk County, Iowa. They later moved to Weeping Water, Nebraska, then south to Oskaloosa, Kansas, and finally about sixty miles farther south to Osage City, Kansas, where his parents are buried. Some accounts suggest his mother may have had Native American ancestry.
While still in Oskaloosa, the young Webb likely began earning his own living as a buffalo hunter and  joining a small crew of teamsters that secured contracts to supply meat to railroad construction workers. Also mentioned among other s research was that Webb participated in a U.S. Government surveying expedition for a rail company that began in 1870 along the Neosho River in Kansas, a likely scenario was that these were private parties who did the dirty work (whose name(s) I cannot track down). The party surveyed through Baxter Springs into Cheyenne and Kaw tribal territory near what is now Johns Creek Reservation, crossed the Arkansas River into Choctaw Territory (Oklahoma), and continued west through Chickasaw and Seminole lands. The project concluded in June 1871, with the crew receiving payment in Arkansas City.
That same summer, Webb headed farther west on his own. He is believed to have tried his hand at mining near the old Maxwell Land Grant in the vicinity of Cimarron, New Mexico, possibly at Lucien Maxwell’s gold mines around Baldy Mountain. Maxwell, recognizing the rich gold deposits on his vast holdings, had earlier attempted to sell the land to the U.S. government as a Ute reservation, but the offer was declined. Following the discovery of gold and copper in the area, miners flooded into Moreno Valley by spring 1867. Maxwell responded by charging fees to squatters, constructing infrastructure such as a 40-mile ditch for placer mining, and building toll roads. A stagecoach route soon connected Elizabethtown to Cimarron and eventually extended to Taos and Santa Fe. Within 14 months, Maxwell’s operations yielded 550 pounds of gold valued at nearly $175,000. He later sold the land grant for $600,000 (equivalent to roughly $13.5 million today) and his Cimarron property for $125,000, investing heavily in government bonds and the Texas Pacific Railroad, investments that ultimately led to significant financial losses.
In October 1870, Maxwell acquired buildings at Fort Sumner, approximately 200 miles south of Cimarron. Tensions over land ownership in the region escalated when the Santa Fe Ring began evicting longtime settlers and displacing the Ute tribe. A protective meeting held on March 30, 1873, helped spark the long-running Colfax County War (1873-1888). It was during this volatile period that Webb reportedly staked a claim at Willow Creek and tended bar in the nearby boomtown of Elizabethtown.
By the mid1870s, Webb had made his way to the legendary cow town of Dodge City, Kansas, where he crossed paths with some of the West’s most iconic figures, including Wyatt Earp and Bat Masterson. He served in various lawful posses and worked as a deputy. In January 1878, newly appointed Ford County Sheriff Bat Masterson called upon Webb and other trusted men to pursue outlaws involved in a train robbery. Among those they hunted were Dave Rudabaugh and Edgar West.
Rudabaugh, a hardened criminal, had earlier formed “The Trio” gang in Texas with Dan DeMent and Michael Roarke. After robbing a railroad construction camp in November 1877, they were pursued by Deputy U.S. Marshal Wyatt Earp, an encounter that famously led Earp to form a lasting friendship with Doc Holliday. The gang later expanded, becoming known as the R&R Gang. Their first train robbery attempt near Kinsley, Kansas, on January 27, 1878, failed. Masterson’s posse, including J.J. Webb eventually captured Rudabaugh and West. According to accounts, Rudabaugh was prepared to fight, but Webb convinced him to surrender peacefully. The pair later turned informant, helping authorities apprehend their former gang members.
In September 1878, amid reports of Cheyenne raiding parties, the government shipped large quantities of firearms to Dodge City for defense. Lieutenant Colonel William Henry Lewis reportedly enlisted Webb and others to serve as Army scouts during this period.
The following year, in 1879, Webb and Rudabaugh were hired by Bat Masterson as gunmen during the violent Railroad Wars in Colorado’s Royal Gorge, a bitter struggle between the Atchison, Topeka & Santa Fe and rival railroad interests. Afterward, the two men drifted south to the booming rail town of Las Vegas, New Mexico, one of the largest and roughest new cities in the West. With six trains arriving daily, Las Vegas attracted eastern travelers, merchants, and a steady stream of outlaws, con artists, and thieves. The east end of town quickly developed a notorious reputation.
A group of former Dodge City lawmen, known as the Dodge City Gang, arrived to impose order. The gang included J.J. Webb, “Mysterious Dave” Mather, Joe Carson, Dave Rudabaugh, and their leader, Justice of the Peace Hoodoo Brown. Under Brown’s direction, Rudabaugh was appointed the city’s first chief of police, while Tom Pickett served as chief of the merchants’ police. Webb once again partnered with Doc Holliday to operate a saloon, where Holliday frequently played cards.
On July 19, 1879, while Webb and Holliday were in the saloon, an ex-Army scout named Mike Gordon became disruptive, shouting at one of the saloon girls. When Gordon stormed outside and fired a shot that missed, Holliday returned fire, mortally wounding him. Holliday stood trial but was acquitted, largely due to Webb’s testimony. Their bond appears to have deepened during this episode; Holliday reportedly gifted Webb a pocket watch engraved on the back: “To my partner and friend John Joshua Webb. July 4, 1879, Las Vegas, NM.” The watch later sold at auction for approximately $30,000 more than a century afterward.
In 1880, Webb was appointed town marshal of Las Vegas and formally joined the Dodge City Gang. Under Hoodoo Brown’s leadership, the group, widely rumored to be involved in train and stagecoach robberies as well as lynchings, held significant influence over the town.
On March 2, 1880, Webb and a deputy entered the Goodlet and Roberts Saloon, where they confronted an armed man named Michael Keliher. When Keliher refused to surrender his weapon and drew his gun, Webb shot him three times, killing him. Though the shooting initially appeared justifiable, rumors quickly spread that Keliher had been carrying $1,900 and that Webb had been sent to retrieve the money. Webb was arrested, tried, and convicted of murder. Many believed the verdict was influenced more by public resentment toward the Dodge City Gang than by the facts of the case. He was sentenced to hang.
On April 30, 1880, Dave Rudabaugh and John Allen attempted to break Webb out of jail. The escape went awry, resulting in the death of the jailer, though Rudabaugh escaped. He was later arrested in December 1880 alongside Billy the Kid.
Meanwhile, Pat Garrett had been elected Sheriff of Lincoln County on November 2, 1880, defeating incumbent Sheriff Kimbrell by a vote of 320 to 179. Although he could not officially assume office until January 1881, Garrett began working immediately with Kimbrell’s support and was also appointed a U.S. Deputy Marshal. Tasked with capturing Billy the Kid and alleged counterfeiters, Garrett raided a ranch near Bosque Grande in late 1880. While the Kid was not there, the posse captured J.J. Webb, who was charged with murder and escaping federal custody, along with George Davis on horse theft charges.
Webb’s death sentence was later commuted to life imprisonment. He found himself sharing a cell with his old associate Dave Rudabaugh. On September 19, 1881, the pair, along with two others, attempted another jailbreak that ended in the death of one escapee. Two months later, on November 19, 1881, Rudabaugh, Webb, and five others successfully escaped by chiseling and climbing through a small hole in the wall.
The fugitives fled to Texas and then into Mexico, where they parted ways. According to later reports, J.J. Webb made his way to Winslow, Arkansas, where he lived under the alias Samuel King. He reportedly died of smallpox while working as a railroad teamster.
However Webb’s involvement in the laying of the iron rails that stitched together the American West may run far deeper than the historical record reveals. It is plausible that he operated under an alias, leading rail crews and securing substantial government grants intended to accelerate the nation’s urgent push for the westward expansion, a top federal priority of the era. Such a role would have afforded him a comfortable, even prosperous existence, one that any prudent man of the time might have protected by quietly assuming a new identity if his past ever threatened to unravel it.
Webb’s story remains a compelling window into the chaotic and morally ambiguous world of the Old West. New details about his life continue to surface, revealing even more layers to this complex frontier character. Check back later for more!