Daniel Boone May – Protecting the Deadwood Stage
The American West, a landscape etched in history with tales of pioneers, outlaws, and lawmen, holds within its vast expanse the story of Daniel Boone May. Reputed to be the fastest gun in the Dakotas, Daniel Boone May carved his legend as a gunfighter, a dedicated lawman, and a steadfast shotgun messenger for the Black Hills Stage & Express Company in the burgeoning territories of South Dakota and Wyoming. His life, a tapestry woven with threads of bravery, quick-draws, and relentless pursuit of justice, embodies the spirit of a bygone era.
Born in Missouri in 1852, Daniel Boone May, the son of Samuel and Nancy May, was one of nine children. He was the seventh child. Early in life, he was known as "Boone," and with his family, he moved to Bourbon County, Kansas, where his father dedicated himself to the life of a farmer. This foundational period instilled in him the values of hard work and resilience, qualities that would later define his remarkable career.
In 1876, Daniel Boone May and an older brother ventured to Cheyenne, Wyoming, a bustling hub in the heart of the West. There, they found employment in the freight business, navigating the challenging landscape where the Black Hills teemed with both opportunistic road agents and the ever-present threat of conflict with the Sioux Indians. This was a dangerous time to be working along the roadways. It demanded courage and skill. Yet, May thrived. He prospered to such an extent that by the year’s end, he had acquired a ranch situated strategically between the Platte River and Deadwood, South Dakota, a testament to his industriousness and ambition.
News of Daniel Boone May‘s valor and unwavering work ethic soon spread, leading to his recruitment as a shotgun messenger for the Cheyenne and Black Hills Stage & Express Company. Tasked with protecting the stagecoaches from bandits and ensuring the safe passage of passengers and valuable cargo, May embraced his role with characteristic determination. In addition to his duties as a messenger, he also served as the station keeper at Robbers’ Roost in Wyoming Territory, a vital outpost along the stagecoach route.
Within a remarkably short period, Daniel Boone May became embroiled in at least eight documented shooting incidents with outlaws, further solidifying his reputation as a formidable force to be reckoned with in the lawless territories. These encounters, often sudden and violent, tested his skills and resolve, adding layers to the legend that was quickly taking shape.
One of the earliest and most notable holdups involving Daniel Boone May occurred in August 1877 when a Deadwood Coach was ambushed at Robber’s Roost. Despite May’s initial inclination to engage the bandits in a firefight, he made the difficult decision to lay down his arms, knowing that a woman and child were among the passengers. The robbers made off with the passengers’ money, weapons, and personal belongings. Shortly after, May encountered one of the bandits, a man named Prescott Webb, in Deadwood. A gunfight ensued almost immediately. Though May sustained a wound to his left wrist, he returned fire as Webb attempted to escape on horseback. May’s shots struck Webb in the shoulder and his horse multiple times, causing it to collapse. Sheriff Seth Bullock swiftly apprehended Webb. Later that same day, Webb’s accomplices, who had aided in the robbery, were also taken into custody, marking a significant victory for law and order in the turbulent town.
By 1878, "treasure coaches" were running regularly between Deadwood and Cheyenne, transporting strongboxes filled with gold and the U.S. Mail. These gold-rich stages became frequent targets for bandits. Following a hold-up on July 2, 1878, the U.S. Postal Service appointed several special agents to bring the outlaws to justice. May, along with ten other men, were appointed U.S. Deputy Marshals. They were equipped with good horses and ammunition.
One of May’s first encounters with bandits as a U.S. Deputy Marshal occurred on the night of September 13, 1878, when he and another messenger were trailing a Cheyenne-bound coach near Old Woman’s Creek in Wyoming Territory. May and Zimmerman surprised the outlaws, and a shootout erupted. May wounded one bandit named Frank Towle, and the others fled without any loot. Leaving the wounded man on the ground, the two messengers pursued the other bandits but were unable to capture them. When they returned to the robbery site, Towle was gone.
On September 26, 1878, the stage failed to arrive when May and other messengers were waiting to escort a coach at Beaver Station on the Wyoming-Dakota border. They headed down the road searching for the coach when they met another messenger who told them it had been robbed and a passenger killed. May quickly joined a posse to go after the outlaws, but unfortunately, they escaped.
The following month, May learned of the hiding place of a road agent named Archie McLaughlin and quickly went after him and his companions. Capturing them north of Cheyenne, the outlaws were sent under guard to Deadwood on the northbound coach. However, the stage never made it. On November 3, 1878, it was stopped by vigilantes who hanged Archie McLaughlin and another man named Billy Mansfield.
The following month, May was in another posse that brought in a road agent named Tom Price. The bandit, who resisted arrest, was wounded before he was brought in.
Late in 1879, May was sent to assist Special Agent William H. Llewellyn in the capture of a mail robber named Curley Grimes.
They tracked the outlaw to Elk Creek, a location about halfway between Rapid City and Fort Meade, and arrested him. That evening as the two lawmen and their prisoner neared Fort Meade, Grimes attempted to escape and was shot and killed by May and Llewellyn.
By this time, May had made such a reputation for himself that he became a target for many of the road agents who repeatedly tried to assassinate him, unsuccessfully.
May also worked as a messenger for the Black Hills Placer Mining Company in the summer of 1880 and was said to have killed at least one road agent during this time.
Shortly afterward, May resigned from the company in September and disappeared from the Black Hills. Next, he was known to have been in Santiago, Chili, in 1883, but after shooting an army officer in 1891, he fled to Brazil. He died of yellow fever in Rio de Janeiro in 1910.