‘All the nerve and skill in the world wasn’t always enough when facing desperate men with nothing to lose’
In the fall of 1889, 35-year-old Gila County Sheriff Glenn Reynolds had the unenviable task of transporting nine prisoners to Yuma Territorial Prison on the far west side of Arizona Territory. The prisoners included the Apache Kid, three of the Kid’s former scout companions, four other convicted Apaches and Mexican embezzler Jesús Avota. Reynolds handcuffed them all but took special precautions with the two he considered the most dangerous—the Apache Kid and Hos-cal-te—shackling their legs and bolting the irons to the floor of the coach. The rest of the Indians crowded in with these two, while Deputy William A. “Hunkydory” Holmes sat up top with driver Gene Middleton. Sheriff Reynolds, mounted on his favorite horse, Tex, rode behind. Reynolds permitted Avota, whom he did not consider dangerous, to ride beside him on a spare horse.
Born into a family of ranching pioneers in 1853, Reynolds had carried on the family business in newly organized counties of Texas and Arizona Territory. When events led him into law enforcement in both places, he had served as a sheriff. Prolific journalist and Western writer William MacLeod Raine described him as “lithe, active, rather tall and very strong,” adding: “One of the best shots in the whole Southwest, he was absolutely fearless, as he had shown on numberless occasions in dealing both with Indians and badmen. In a land where men are quick on the trigger, Glenn Reynolds commanded unusual respect for his nerve and skill.” All the nerve and skill in the world, however, wasn’t always enough when facing desperate men with nothing to lose. The Apache Kid was about to launch a break from custody that would result in freedom, however temporary, for the prisoners and tragedy for the men guarding them.
Glenn Reynolds was born in Shelby County in east Texas, cotton-raising country. In 1859 his family, led by patriarch Barber Watkins (“Watt”) Reynolds, moved west to rangeland better suited for raising cattle, in Buchanan County (renamed Stephens County in 1861). In 1866, when Glenn was 12, the family again moved farther west, this time making their headquarters in the historic Old Stone Ranch in the southwestern section of unorganized Throckmorton County.
Soon after their arrival Watt Reynolds traveled to Weatherford, about 100 miles away, for supplies, taking his daughters and an older son with him. Left at the ranch were Mrs. Reynolds, 12-year-old Glenn and his 9-year-old brother, Phin. Two passing hunters spent a night at the ranch, which proved fortunate, for the next morning a party of Indians, believed to be Kiowas and Comanches, attacked. The hunters, aided by young Glenn, drove them back, but not before the marauders had driven off most of the Reynolds’ horses and 500 head of their cattle.
Despite such losses, the Reynolds ranch prospered, with Glenn making a major contribution to that success. He was only 17 when his father entrusted him with 1,000 head of Longhorn cattle on a drive to Kansas. On arrival in Abilene he found that the Longhorns, valued at $4 a head in Texas, could fetch double that amount at the railhead. But Glenn even bettered that hand, shipping his cattle on to Chicago, where they brought $20 or more a head. He returned to Texas with $8,000 in profit.
Although he raised his sons as working cowboys, Watt Reynolds made sure not to neglect their education in other fields. Since no school was available nearby, he employed a governess to teach his younger children, and in 1874, when Glenn was 20 and Phin 16, he sent the young men off to the Jones Commercial College in St. Louis for advanced studies.
Briefly in 1875 Glenn tried his hand at mining in Colorado Territory, but that proved unsuccessful, and he returned to Texas and took up residence at a family ranch in Haskell County. On March 2, 1876, he married Augusta “Gustie” Russell, an 18-year-old Illinois native. The first of their six children was born at the remote ranch house on February 4, 1877, with only Glenn and his 15-year-old sister, Sallie Ann, to aid in the delivery. The baby boy was named Elmer Glenn. Siblings Watt, Bessie, Gustie, George and Pearl followed over the years.
In June 1878 Glenn Reynolds was a member of a sheriff’s posse that set out to arrest John Larn, a former Shackelford County sheriff, and his onetime deputy, John Selman. The former lawmen had turned to outlawry. Selman eluded the posse, but the sheriff arrested Larn and locked him up in the Albany hoosegow. On the night of June 23 a lynch mob broke into the jail and, finding Larn shackled to the floor, shot him to death instead. The killers’ identities remained secret, but it was suspected that Glenn and other young men from the Reynolds and Matthews families—the leading ranchers of the region and the principal victims of Larn’s depredations—were leaders in the enterprise.
On March 25, 1879, local officials organized Throckmorton County, and Glenn Reynolds became its first sheriff. He served until November 1880, when he declined to run for re-election in order to devote his energies to the raising of sheep as well as cattle. There is no record of him shooting anyone during his term as sheriff. The Fort Worth Daily Democrat of February 9, 1882, reported he had shot and killed a man described as a “Mexican desperado” in an argument over a billiards game in a Fort Davis, Texas, saloon, but confirmation is lacking.
Reynolds was a popular figure in that section of Texas, and his fellow ranchers, as a token of the great esteem in which he was held, presented him with a beautiful pocket watch mounted in two gold cases and engraved GLENN REYNOLDS, ALBANY, TEXAS 1884. A sheep was engraved on the interior of one face, a steer on the other, indicating his dual roles as sheepman and cattleman. The expensive timepiece became Reynolds’ most prized possession.
When the U.S. government removed the tariff on wool in 1885, the price plummeted, and many sheep raisers in the Southwest went broke. Reynolds was among those hard hit financially. He disposed of his sheep for whatever he could get, rounded up his cattle and horses, sold his ranch and headed farther west.
Reynolds and his ranching friend Jess Ellison drove their combined herd of 3,000 cattle and 200 horses to the Texas & Pacific railhead at Weatherford, Texas, and shipped them to Arizona Territory. At Bowie Station, Cochise County, Reynolds unloaded his livestock and trailed the herd 200 miles north through the San Carlos Apache Indian Reservation to the grasslands of the territory’s Tonto Basin, where he established a ranch on a stream in the Sierra Ancha in early 1886 and sent for his family.
He did not remain long out of public affairs in his new home. In November 1886 the Apache County Board of Supervisors appointed him justice of the peace at Holbrook, a lively new town on the Atlantic & Pacific Railroad. Glenn was soon drawn into the bloody battle that has come to be called the Tonto Basin War or Pleasant Valley War. Originating as a feud between the Graham and Tewksbury families (cattlemen and sheepmen, respectively), this sanguinary conflict eventually involved fighting men throughout central Arizona Territory.
On September 21, 1887, Reynolds, acting as a deputy under Yavapai County Sheriff Billy Mulvenon, participated in a gunfight in which John Graham and Charlie Blevins were shot and killed. The following November, Al Rose, a leading Graham partisan, met his end at a remote ranch. According to Joe McKinney, another deputy of Mulvenon, Reynolds killed Rose, blasting him with a shotgun, though for years Reynolds family members adamantly denied that Glenn did the shooting. Another version had Rose hanged by vigilantes led by Reynolds’ old friend Jess Ellison, with Reynolds one of the party.
On August 11, 1888, a heavily armed party of two dozen or more men forcibly took Jamie Stott, Billy Wilson and Jim Scott—believed to be Graham supporters and aiders and abettors of rustlers—and hanged the trio at Stott’s Mogollon Rim ranch, 60 miles from Holbrook. Contemporaries fingered Glenn Reynolds and Tom Horn—who would gain fame and infamy as an Army scout, rodeo performer and hired killer (and who was eventually hanged for murder in Wyoming)—as participants in this lynching, though no one was ever officially charged.
These events cast Reynolds as a deadly member of the Tewksbury forces and a man marked for death by the Graham faction. To avoid assassination, he had to disguise himself when traveling.
At the peak of the Pleasant Valley troubles, George, the infant son of Glenn and Gustie Reynolds, fell seriously ill. Reynolds dispatched a rider on a fast horse to Globe to obtain medicine. So dangerous were the trails that Reynolds padded the hooves of the horse and tied back the rowels of the rider’s spurs in an effort to maintain silence. Despite the precaution, however, someone intercepted and shot the horseman. Glenn and Gustie never received the medicine, and the baby died. One of Glenn’s brothers came out from Texas to Arizona Territory to see the family, but due to the wild, lawless state of the country, he got only as far as Globe before forced to return.
Reynolds had had a bellyful. He told Gustie he could no longer maintain a proper home in which he frightened his children with his disguises; raise a family where a baby died because medicine could not be safely delivered; or live in a land so wild his brother could not reach them because of the danger. The Reynolds family packed up and moved to Globe.
But Reynolds could not long remain out of law enforcement and would again put himself in harm’s way. In November 1888 he was elected sheriff of Gila County. As deputies he appointed a trio of tough fighting men—Jerry Ryan, Hunkydory Holmes and Floyd Blevins. (He did not deputize Tom Horn, as Horn later claimed in his autobiography.)
Terrorizing the scattered settlements of Arizona Territory at the time were a number of renegade Apaches, the most ferocious of whom whites called the Apache Kid. One observer described him as a “short, stocky, full-blooded Indian…wiry and bold, quick as lightning and as cunning as a fox.” As a scout at the San Carlos Agency, working under the celebrated chief of scouts Al Sieber, the Kid had demonstrated outstanding leadership ability. But during an altercation with his Indian scouts, Sieber was shot in the ankle, crippling him for life. Enraged, he blamed the Apache Kid for the injury and insisted the Kid and his companions stand trial. In June 1888 the Apache Kid and the other scouts were convicted of assault in the Second Federal District Court at Globe and ultimately sentenced to 10 years in prison.
But the Indian Rights Association, an organization of whites concerned with the mistreatment of Indians, questioned the validity of the federal convictions and brought a suit that reached the U.S. Supreme Court. On April 15, 1889, that tribunal issued a writ of habeas corpus, releasing the prisoners for another trial at the territorial court in Globe.
Authorities returned the Apache Kid and his fellow scouts to San Carlos. Sieber, angered by this turn of events, presented Sheriff Reynolds with a list of Apaches charged with crimes and demanded their arrest. Heading the list was the Apache Kid, the man Sieber held most responsible for putting him on crutches. With the help of his deputies and troops stationed at the San Carlos Agency, Reynolds arrested all of the wanted men but one, an Apache named Massai (see related Indian Life story in December 2012 Wild West).
On October 23, 1889, the Indians appeared in territorial court. Judge Joseph H. Kibbey, who would later serve four years as governor of Arizona Territory, presided over their trial. Sieber, the chief witness against the accused, named without hesitation the Apache Kid as the man who had shot him and three other defendants as accessories in the attack. The jury returned a verdict of guilty, and Kibbey sentenced each of the four defendants to a seven-year term in the Yuma Territorial Prison. Sheriff Reynolds locked them up in his county jail together with the Mexican embezzler, Avota, and six other Apaches convicted of various crimes.
Moving quickly to relieve the pressure on his overloaded calaboose, Reynolds within a week obtained commitment papers for his Yuma-bound prisoners and $400 in expense money to make the journey. For transport he arranged use of one of the Middleton Stage Line’s big sturdy coaches. To reach the Southern Pacific railhead at Casa Grande and entrain the prisoners for Yuma required a two-day coach trip with an overnight stop at Riverside, the stage station on the Gila. None of the stage line’s drivers would undertake the long trip with a load of dangerous Apaches, so company owner Gene Middleton himself reluctantly took the reins.
Leaving Deputies Ryan and Blevins to oversee the county jail and the remaining inmates, Reynolds brought along Deputy Holmes to help guard the prisoners consigned to Yuma. Some folks expressed surprise at the sheriff’s decision, but Reynolds, with supreme confidence in his own abilities and high regard for Holmes, scoffed at their concern.
Hunkydory Holmes, like his boss, was a native Texan. As a prospector in Arizona Territory, he had struck a rich silver vein. When another prospector, Banjack Marco, tried to jump his claim, Holmes shot him dead and spent most of his fortune winning an acquittal before pinning on a deputy sheriff’s badge. Holmes gained popularity by entertaining saloon customers with his original poems, including one entitled “Hunkydory,” from which he derived his nickname.
Subsequent events caused many to question why Reynolds decided to convey nine convicted felons through rough country guarded only by himself and one other man, but according to later newspaper reports, the Gila County supervisors were responsible for this decision when they refused to grant him additional deputies for the trip. Al Sieber reportedly offered the sheriff an escort of Apache scouts to assist him in the journey, but Reynolds is said to have responded: “I don’t need your scouts. I can take these Indians alone with a corncob and a lightning bug.” That was a pretty cocky answer, but given the fact that several of his prisoners were former scouts for Sieber, Reynolds may have simply distrusted any of the Apache scouts, former or current.
At dawn on November 1, 1889, the stagecoach with its nine sullen, manacled passengers rolled out of Globe. The ride to the Gila, the river crossing and the arrival at Riverside proved uneventful. At the stage station that night Reynolds and Holmes took turns watching the handcuffed prisoners, who were required to sleep sitting up on benches, their backs to a wall.
After a quick predawn breakfast, the journey resumed the next morning. Middleton warned Reynolds that four miles down the road they would come upon a steep, winding grade nearly a half-mile long. His horses, he said, could not pull the heavily laden stagecoach over this stretch of sandy rise, and it would be necessary to unload the passengers and walk them to the top of the hill. Hearing this discussion, the Apache Kid saw a chance for a mass escape, and when the Indians were loaded back into the coach, he gave instructions to the others in his native language, which the white men didn’t know.
Upon reaching the grade, Reynolds unloaded all of his prisoners with the exception of the Apache Kid and Hos-cal-te, whom he kept shackled in the coach. Reynolds cuffed the other Indians in pairs and lined them up behind the stage. Avota went first, followed by Reynolds, carrying a shotgun. Next came three pairs of Indians, with Holmes, Winchester rifle in hand, bringing up the rear. Middleton whipped up his team, and the stagecoach moved on ahead, quickly putting distance between it and the strange column following.
Suddenly, at the signal of an Apache war whoop, the pair of Indians behind Reynolds leaped on him, pinning his arms to his body with their free hands. Simultaneously the two prisoners directly ahead of Holmes turned and attacked him. They wrested his rifle from his grasp, knocked him to the ground with its butt and shot him in the head. The third pair of Indians joined those engaged with Reynolds, and the four Apaches soon overpowered the sheriff, taking him to the ground. The Indian who had shot Holmes ran up and put another bullet from the deputy’s rifle into Reynolds’ body.
The Indians quickly removed the sheriff’s shotgun, pistol and keys to their shackles. When Reynolds stirred and tried to rise, the Apaches shot him again with his own pistol and emptied both barrels of the shotgun into his face, obliterating it. The Indians stripped the bodies of the sheriff and his deputy of their clothing and belongings and systematically mutilated the corpses. They stole, among other Reynolds’ effects, the gold watch he had so highly prized.
Meanwhile Avota, fearful for his own life, had fled the scene of carnage and chased after the stagecoach struggling up the sandy grade. Middleton, hearing the shots behind him, thought the officers were just target shooting, or, perhaps experiencing some trouble with the prisoners, had fired the weapons to bring them under control. When Avota caught up with Middleton and excitedly told him the other prisoners had killed the sheriff and his deputy, the stage driver was unbelieving. He pulled up his horses and set the brake. He was about to get down and investigate when a rifle bullet slammed into his neck, toppling him to the ground. Two Indians had chased Avota up the hill, and one, carrying Holmes’ Winchester, stopped, took careful aim and shot the driver. Seeing him fall and believing him dead, they climbed into the coach and, with the keys taken from the pockets of the slain sheriff, released the Apache Kid and Hos-cal-te. The terrified Avota by this time had disappeared into the brush.
The Indians grabbed Middleton’s weapons and took the valuables from his prone body. Anxious now to complete their dramatic escape, they did not wait to mutilate the driver’s body but, whooping in jubilation, ran off toward the hills. Gene Middleton, although severely wounded and weak from blood loss, was still alive. When the Indians had gone, he struggled to his feet and, with slow, painful steps, made his way back four miles to the Riverside stage station and spread news of the catastrophe.
Avota, meanwhile, had caught a ranging horse from a nearby ranch and set out for Florence, 30 miles distant, to turn himself in and report the escape and murders. He would eventually receive a full pardon for his actions in the affair.
The escape of the eight convicted Apaches and the brutal murders of Sheriff Reynolds and Deputy Holmes set off the largest manhunt in Arizona history. Within days Lewis Wolfley, governor of Arizona Territory, proclaimed a $500 reward for each of the escaped Apaches “if captured and arrested alive, or upon evidence duly authenticated of their having been unavoidably killed by any officer or person attempting such capture or arrest.” In simpler words the eight were “wanted, dead or alive.” The lure of $500 for each of eight fugitives spurred citizenry and lawmen alike, who soon captured or killed all but the wily Apache Kid, who lived on for years as a feared outlaw in Arizona Territory and Mexico, the rewards for him totaling an amazing $5,000 (about $135,000 in today’s money). Various stories spread regarding the circumstances of his death, but none were ever really confirmed, and how and when he died remains a mystery.
A month after the mass escape a rumor spread that Gustie Reynolds was considering a damage suit against the members of the Gila County Board of Supervisors for their action (or inaction) that led to the death of her husband. The Prescott-based editor of the Arizona Weekly Journal-Miner supported the idea, writing that the supervisors were “certainly reprehensible in the extreme for their action in refusing to allow the sheriff a proper guard to accompany him in the transportation of prisoners of the character they were.” The editor added: “[Reynolds] had eight desperate and bloodthirsty Apaches, the worst of the tribe, and one Mexican prisoner. The only assistance the supervisors allowed him was one deputy, who was killed with the sheriff. If Mrs. Reynolds can make the action against the penurious officials of Gila County for about $25,000, the general verdict will be ‘served them right.’” But the rumor was unfounded, or Gustie changed her mind; there was no lawsuit.
Sheriff Glenn Reynolds was buried in the Globe cemetery beside the grave of his infant son, George. In 1907 Al Sieber joined him there after being killed by a falling boulder during the building of the Roosevelt Dam. The very tough Gene Middleton lived another 40 years after surviving the bloody events of November 1889. He died in 1929 at age 68. In 1890 rurales in Mexico found Reynolds’ gold watch on the body of a slain Apache man and returned it to Gustie, who, after the death of her husband, had returned to Texas and was living with her children in Albany, Shackelford County.
R.K. DeArment is a frequent contributor to Wild West and an award-winning author of many books and articles about gunfighters and lawmen. For further reading see his Bravo of the Brazos: John Larn of Fort Griffin, Texas; Jane Eppinga’s Arizona Sheriffs: Badges and Bad Men; and Earle R. Forrest’s Arizona’s Dark and Bloody Ground.