The stagecoach shotgun messenger who worked his weapons on the dangerous road from Deadwood earned a reputation for killing robbers.
In June 1879, on the trail to the great Black Hills gold bonanza, a young diarist named Rolf Johnson met a man he recognized by name as Boone May, shotgun messenger on stagecoaches plying the road from Deadwood, Dakota Territory, to the Union Pacific depots some 200 miles south. As Johnson noted in his diary, May was “the most noted scout, detective, Indian fighter and shooting man of the Black Hills…[who] has had more fights with Indians, road agents and desperadoes, captured more stage robbers and horse thieves, and killed more men than any other man in the Black Hills.” A tall, impressive figure, May wore a long linen duster with a red silk handkerchief at his throat. Strapped to his waist was a cartridge belt and ivory-handled six-shooter. His eyes, recalled Johnson, were peculiar, “an indescribable hue between yellow, green and gray and had a curious, restless look about them.” He summed up May as a man he “would instinctively fear.”
Running into May again several months later, Johnson witnessed a demonstration of his marksmanship. “I saw Boone May make a splendid shot,” the diarist noted. “He drew his six-shooter and fired at a small blackbird that was running along the road over 60 yards away and dropped it dead.”
Badmen had just as much reason to fear the man as blackbirds did. May’s business was stopping outlaws, and no one in Dakota Territory knew that tough business any better or pursued it with such fervor as May. His daring deeds caught the attention not only of Johnson but also of Ambrose Bierce, who worked for a Black Hills mining company before becoming a noted American author. Afterward, though not on the run like Wild Bunch outlaws Butch Cassidy and the Sundance Kid, Boone May traveled to South America and more than likely died there, far from his old Dakota stamping grounds.
Daniel Boone May, born in Missouri in 1852 and raised on a Kansas farm, was the seventh of nine siblings. Boone and brothers Bill and Jim left for the Far West in the early 1870s and joined the Deadwood gold rush in 1876. Bill devoted his energies to prospecting while his brothers established a pair of team changing stations along the stage route between the gold camps and the railroad at Cheyenne. Stagecoaches traversing that desolate road soon fell prey to road agent gangs, and the Cheyenne & Black Hills Stage Line began enlisting shotgun messengers, men of nerve and demonstrated shooting prowess, to protect passengers, mail and gold shipments. Boone and Jim May hired managers for their stations and signed on as messengers. Bill occasionally came down from the hills to join them. Over the next few years this company of messengers became legendary. Best remembered were the exploits of Boone May.
In August 1877, three aspiring road agents—Prescott Webb, C.P. (“Perry”) Wisdom and G.W. Conner—conspired to rob the stage from Deadwood. Boone May got wind of the plan. Enlisting the aid of Mike Goldman and Jim Lebby, gamblers of gutsy and gun handy repute, May planned to thwart the robbery and capture the highwaymen. He and his associates, heavily armed, joined the only scheduled passengers, two male adults, in the coach.
But before the stage left Deadwood a problem arose. A woman and a small child came aboard. May objected strenuously, but the woman insisted, and the stage set out. Fearful these innocents might be injured, Goldman and Lebby lost much of their enthusiasm for a gun battle with bandits.
The robbers, masked and brandishing weapons, appeared as anticipated and halted the driver. Boone May, rifle in hand, struggled to leap from the coach and fight it out, but the others restrained him. Disgustedly, he submitted to a search by the robbers, who found little of value except the weapons of May and his friends. The robbers then debated openly as to the advisability of killing May, who had made no secret of his hatred of road agents and his aim to hunt down every one. Finally, they decided against the execution, a choice they would come to regret.
In Deadwood a few weeks later, May and Goldman spotted Webb, one of the robbers. Recognizing them at the same time, Webb drew two revolvers and began shooting. A bullet hit May in the left arm, but he returned fire, emptying his six-shooter and a backup derringer at Webb, who, dodging and weaving, avoided the shots. He snatched the reins of a rail hitched horse, vaulted into the saddle and spurred for the hills. Sheriff Seth Bullock and two deputies, drawn to the scene by the rattle of gunfire, opened up on the fleeing Webb, striking the stolen horse and bringing rider and mount tumbling to the ground. Even with a gunshot arm, Boone May fought on. Grabbing a bystander’s rifle, he put a slug in Webb’s right shoulder, and the fight was over.
Later that day, officers tracked down Webb’s pals, Wisdom and Conner, and arrested them after a brief resistance. With a backlist of cases on the docket, Deadwood authorities happily relinquished the prisoners to the Wyoming Territory courts. May’s arm wound was serious—the bullet, striking just below the elbow, had hit a bone and split, one piece exiting the arm, the other having to be removed by a surgeon. He was still recovering when messenger Jesse Brown and special deputy W.M. Ward took the prisoners to Cheyenne on September 1.
The three accused highwaymen were tried separately in December, and by that time May had recovered sufficiently to appear as the principal prosecution witness. The case against Wisdom led off. May described the robbery and named the defendants as the ones who had committed the crime. He gave an account of the gunfight and Webb’s arrest in Deadwood and estimated that as many as 50 shots were exchanged in that clash. A vigorous cross-examination did not shake his testimony. The only other prosecution witness was Mike Goldman, who corroborated May’s account. Defense counsel produced two witnesses who placed Wisdom far from the crime scene. The three defendants were called to the stand, and all denied participation in the robbery. When jurors failed to agree on a verdict in the Wisdom case—eight voting for acquittal, four for conviction—the judge dismissed the territorial indictments against the defendants but bound them over to answer federal charges.
When federal court convened in March 1878, U.S. attorneys, claiming an inability to produce prosecution witnesses, requested and received dismissal of all charges, and the three defendants walked free. To May, this development was inexplicable, for he, the foremost witness against the accused, was certainly ready and willing to testify again. The outcome of these cases did nothing to strengthen his faith in the court system and probably contributed to his growing reputation as a hunter of outlaws who would rather kill than capture his quarry.
Road agents Jim Wall and Dunc Blackburn, well aware of May’s deadly renown, decided to kill him. They stopped the coach from Deadwood on October 9, 1877, but found just one passenger, a woman, whom they left alone, and no treasure. The bandits told the driver they were really after May and would kill him if possible. Fortunately for May, or possibly the pair, Boone was nursing his arm in Deadwood.
Almost a year passed before May again locked horns with road agents. On September 13, 1878, near Old Woman’s Fork, a gang of six men held up the coach from Cheyenne, carrying two passengers. The highwaymen took the few dollars the man carried but did not bother his female companion. They tore open the mail sacks and removed all valuables before ordering the driver to move on. Meeting the stage from Deadwood several miles up the road, the driver alerted its occupants to the presence of road agents. The Deadwood stage, carrying two passengers and mail, also held a treasure box of gold behind the boot. Boone May and John Zimmerman guarded the shipment as outriders. The coach continued on, but the mounted messengers dropped back some 200 yards, hoping to surprise the robbers.
As expected, the robbers stopped the coach and were busily rifling the mail sacks when May and Zimmerman, now afoot, approached in the darkness. Zimmerman carried a rifle, May a shotgun. They got within 15 feet of the bandits before being discovered. A gun battle erupted. After May dropped one of the gang with a blast of buckshot, the others fled, two of them limping from wounds. The driver whipped up his team, and the coach careened down the road. May and Zimmerman mounted up and followed the stage, leaving the dead robber and scattered mail pouches in the road.
A party from the next station returned to the scene that morning to pick up the scattered mail and look for the body of the robber May had killed. A pool of blood lay on the road where the man had fallen, but the body had vanished. For months the identity of the dead road agent and what became of his body remained a mystery.
Less than two weeks later at Canyon Springs station, the Tom Price Gang pulled off the most successful and widely reported stagecoach robbery of the period. On September 26, gang members converged on the station, tied up stock tender William Miner and, with leveled rifles, awaited the arrival of a treasure-laden coach conveying some $27,000 in gold and currency to the railroad. The stage carried one passenger, Hugh Campbell, as well as guards Scott Davis, Gale Hill and Eugene Smith. They were met at the station with a hail of bullets. Campbell was killed and Smith rendered unconscious when around grazed his head. Hill hit an outlaw with a rifle bullet before he passed out from two serious wounds. Amid the confusion, Davis exited the coach from the opposite side and, after trading shots with the bandits, realized he was fighting alone. He slipped away and walked seven miles to a ranch. There he obtained a horse and headed for the next station, where he knew messengers May, Billy Sample and Jesse Brown were waiting to escort the treasure coach on to Cheyenne.
Davis returned to Canyon Springs with his fellow messengers to find the outlaws had departed with the loot. Smith had recovered, but Hill was in bad shape. Campbell’s body lay where it had fallen. The stock tender had worked free of his bonds and was off to Deadwood to sound the alarm.
Miner returned with many riders, including Sheriff Bullock, who organized posses, and Dr. L.F. Babcock, who saved Hill’s life. May was active in one of the posses trailing the bandits, who had split up following the robbery. Within days, May’s posse brought John H. Brown, a confessed gang member, into Fort Laramie. Then, acting on information provided by Brown, they collared Charles Henry Borris, another suspect.
Boone and brother Bill later joined a large posse on the trail of three gang members, two of whom had suffered wounds during the Canyon Springs battle. They cornered the fugitives in a patch of woods, but the outlaws escaped in the darkness, in their haste leaving behind some of the gold.
Back in Deadwood, Bill and Jim May helped capture two other suspected gang members—Archie McLaughlin and Billy Mansfield. After intense interrogation, these two divulged the location of Tom Price’s hideout. The May brothers and other posse members surrounded the camp and, after a hot gunfight, captured the gang leader, who was severely wounded in the exchange.
Dr. Babcock attended Price in Deadwood. According to messenger Jesse Brown, for three weeks “everything [Price] ate passed through the hole in him,” but the gang leader recovered enough to travel, and in February 1879 Boone May took him to Cheyenne to stand trial. Interviewed by The Cheyenne Daily Sun, May called his prisoner “a shrewd rascal” and predicted, “There will have to be much new hemp before the country is rid of these pests.” The Sun called May “one of the bravest and most intrepid thief catchers and stage messengers in this region.” In the May 1879 term of court, Price was convicted of highway robbery and sentenced to five years in prison. He was released after serving less than four years.
Among the suspects rounded up in the months following the Canyon Springs robbery was a character named Joe Minuse, who, under severe interrogation, divulged the names of other gang members and their many crimes. From Minuse officers learned the identity of the robber slain by Boone May during the holdup attempt the previous September and what had happened to his body. Frank Towle had fallen under May’s fire, said Minuse. After the stage rolled on and the shotgun messengers followed, the other gang members emerged from hiding, dragged Towle’s body into the brush and dumped it in a shallow grave.
With this information, May rode out to the robbery scene, found Towle’s grave, dug up his remains and severed the outlaw’s head. Toting the grisly specimen, he rode almost 200 miles back to Cheyenne, where he hoped to collect the reward for the road agent, dead or alive. Laramie County commissioners considered his claim for weeks and finally denied it on the grounds May had not proven he, in fact, had killed Towle. May then took his case and the continually deteriorating head to Carbon County, which also rejected his claim. In high dudgeon, he abandoned his campaign for the reward and disposed of the head in a shallow hole outside Cheyenne. The Sun reported that stray dogs or pigs later smelled out the head, dug it up, gnawed it and left it in the street, “its ghastly jaws grinning hideously at passersby.”
Two months later, May was involved in the controversial death of another road agent. He and Jesse Brown were returning to Deadwood from a trip south with the treasure coach. With them in the stage was lawman James L. “Whispering” Smith, who was conducting outlaw Cornelius “Lame Johnny” Donohue to the Black Hills for trial. Near Buffalo Gap station on the night of July 1, 1879, a band of armed vigilantes stopped the coach. The masked men yanked Donohue off, dragged him, kicking and struggling, to a tree and hanged him.
Afterward, there were grumbles in some quarters about the failure of May and the other fighting men to defend the prisoner, even rumors they were in on the lynching, but no charges were filed. Most folks considered Lame Johnny’s demise good riddance.
Boone May’s involvement in any outlaw’s death seemed to raise controversy. Acting in his capacity as a deputy U.S. marshal, May teamed up with federal agent William Llewellyn in February 1880 to capture Leon “Curly” Grimes, wanted for post office robbery. They found Grimes with a bull train some 40 miles south of Deadwood and arrested him without incident. Placing their handcuffed ward on a borrowed horse, they started back to Deadwood.
At sunset it began snowing and Grimes pleaded to have the shackles removed before his hands froze. He promised to make no attempt to flee. The officers removed the handcuffs, and the three rode on into an increasing blizzard.
At the height of the storm, with visibility severely limited, Grimes suddenly spurred his horse into a gallop, ignoring the shouts of May and Llewellyn to stop. The officers opened fire, and Grimes tumbled from the saddle, riddled with bullets. Leaving the body where it lay, the officers continued on to Fort Meade and reported the incident. When the storm subsided, a detail went out and buried the outlaw’s frozen body. Some in Deadwood grumbled, noting May’s escalating reputation as an outlaw killer, and a coroner’s inquest found the killing unjustified. May and Llewellyn were charged with murder and released on $10,000 bail provided by men of substance.
Defending them was The Cheyenne Leader editor, who contended that Dakota folks were “a little too fast” in condemning May and Llewellyn for the killing of a notorious road agent. “The people want to see every bandit in the country fixed, but as soon as one is planted, [they] generally succeed in creating sympathy for the dead robber.”
That August, May and Llewellyn stood trial in Deadwood. The crowded courtroom broke into cheers as the jury delivered a “not guilty” verdict without ever leaving the jury box.
While awaiting trial, Boone May took employment with a mining concern as a special messenger and bodyguard to Ambrose Bierce, the company’s general agent. In a letter to his superiors, Bierce praised May as “a man who has captured and killed more road agents and horse thieves than any man in the West; whose name is a terror to all evildoers in the [district]; whose fidelity and trustworthiness are as famous as his courage.” However, with a touch of the sardonic humor that became his hallmark as a writer, Bierce listed his employee’s name on company rolls as BOONE MAY, MURDERER.
In a piece written years later, Bierce described one dark night when he was at the reins of a wagon carrying a shipment of gold ore, and May sat beside him, a rifle in a leather scabbard across his lap. A mounted highwayman suddenly appeared at their side and with leveled weapon ordered, “Hands up!”
“With an involuntary jerk at the reins I brought my team to its haunches and reached for my revolver,” Bierce recalled. “Quite needless: With the quickest movement that I had ever seen in anything but a cat—almost before the words were out of the horseman’s mouth—May had thrown himself backward across the back of the seat, face upward, and the muzzle of his rifle was within a yard of the fellow’s breast!” What happened then Bierce coyly left to the reader’s imagination, saying only that as he related this tale, Boone May had long been dead, and of the three men there in the forest, Bierce himself was “the sole survivor.”
Bierce may have embellished this tale, but undoubtedly he greatly admired May as a fearless and resolute fighting man. He staunchly defended his employee in letters to the home office, saying May performed a vital service guarding valuables “in a country infested with robbers and cutthroats.” But Bierce’s superiors objected to a notorious gunman and accused murderer on the payroll. The dispute led to Bierce’s resignation, and May also lost his job. Bierce did better in the newspaper business, and he went on to write short stories favorably compared with those of Edgar Allen Poe and Bret Harte. He mysteriously disappeared in Mexico in 1913.
Following his murder acquittal, Boone May led a group of Deadwood friends on a hunting expedition. The men bagged plenty of game, but Pine Ridge Agency Indians, angered by white encroachment on their hunting grounds, complained to agent Valentine McGillycuddy. He reportedly gave the Indian leaders warrants for the arrest of May and his party. An inflammatory dispatch from Deadwood said the Indians had boasted “they would take Boone May, dead or alive” and reported that reinforcements were coming to help May.
A news service story appearing in papers as distant as Maine reported that the Indians, 100 strong, had driven every white man from their side of the Little Missouri and declared they would capture May if they had to kill every one of his companions. Boone May and 70 others waited on the opposite bank, “determined to resist to death.”
Although McGillycuddy denied having given the Indians arrest warrants for the white hunters and later claimed a clash was avoided, lawman A.M. “Cap” Willard, a member of the hunting party, said there was a fight. When the Indians mounted a surprise attack, May stood alone by the fire, banging away with his rifle. The weapon jammed just as a brave charged him. “He dropped his rifle, pulled his six-shooter, fired and the Indian fell dead.” Willard said the Indians withdrew after a short battle, leaving behind six dead warriors and 22 dead ponies. One wounded warrior, claimed Willard, “Boone May soon put out of his misery with a knife.”
Willard said May was a fatalist who believed a man’s death was predetermined. To prove his point to a companion after the fight, he pointed to a dead Indian, remarked that the Indian had missed him twice before May killed him and asked, “Now, what would you call that?” The response ended the argument: “I would call that damn poor shooting.”
Soon thereafter Boone May departed the Black Hills. According to infrequent reports received by friends in Deadwood, he traveled to Bolivia and Peru and became involved in mining ventures. After killing a Peruvian army officer, he escaped to Brazil, only to shoot a Brazilian in a fight over a woman, or so the story goes. He fled again, this time to Venezuela. May wrote a friend that he was suffering from yellow fever. Soon after, the letters stopped coming.
Brother Bill May’s mining ventures had proven successful, and by the time he died about 1900, brother Jim had also passed, leaving Boone heir to the May fortune. Executors could not find him, and the man described in 1903 newspapers as “the most noted of all the messengers…known for his fearlessness and for the deadly execution he exhibited in the numerous encounters with the road agents who infested the region,” missed out on a substantial inheritance.
R.K. DeArment is the award-winning author of many Western books and a frequent contributor to Wild West. For further reading, see DeArment’s Assault on the Deadwood Stage: Road Agents and Shotgun Messengers, which will be released early in 2011 by the University of Oklahoma Press.
Originally published in the December 2010 issue of Wild West. To subscribe, click here.
