Said to have been the fastest gun in the Dakotas, Daniel Boone May, began his life in Missouri in 1852. Going by the name of “Boone,” he was the son of Samuel and Nancy May, the seventh of nine children. Later, he moved with his family to Bourbon County, Kansas, where his father worked as a farmer.
In 1876, he and an older brother moved to Cheyenne, Wyoming, where they worked in the freight business. During this time, the Black Hills were crawling with road agents and hostile Sioux Indians – a dangerous time to be working along the roadways. May did so well, that he bought a ranch between the Platte River and Deadwood by the end of the year.
Hearing of Boone’s bravery and work ethic, he was soon recruited as a shotgun messenger for the Cheyenne and Black Hills Stage & Express Company. He also served as the station keeper at Robbers’ Roost in Wyoming Territory.
Within just a few years, May was thought to have been in at least eight shooting incidents with outlaws.
One of the first hold-ups he was involved in was in August, 1877, when a Deadwood Coach was held-up at Robber’s Roost. On this occasion, though May wanted to fight it out, he lay down his arms, as a woman and child were in the coach, and the robbers made away with the passenger’s money, weapons and personal goods. A short time later, he ran into one of the bandits, a man named Prescott Webb, in Deadwood and within no time, gunfire erupted between the pair. Though May was hit in the left wrist, he returned fire as Webb jumped on a horse to flee. May’s shots hit Webb in the shoulder, and the horse several times, bringing it down. Webb was quickly arrested by Sheriff Seth Bullock and later that day, Webb’s companions who had aided in the robbery, were also arrested.
In 1878, “treasure coaches” were running regularly between Deadwood and Cheyenne, carrying strong boxes laden with gold, as well as the U.S. Mail. These gold-rich stages became the often target of bandits and after one of these coaches was held up on July 2, 1878, the U.S. Postal Service appointed a number of special agents to bring the outlaws to justice. May and ten other men were soon appointed as U.S. Deputy Marshals and equipped with good horses and ammunition.
One of May’s first run-in 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 which was approached by bandits near Old Woman’s Creek in Wyoming Territory. May and Zimmerman surprised the outlaws and shooting erupted. May wounded one bandit named Frank Towle and the others fled without any booty. Leaving the wounded man on the ground, the two messengers went after the other bandits but were unable to capture them. When they returned to the robbery site, Towle was gone.
On September 26, 1878, when May and other messengers were waiting to escort a coach at Beaver Station on the Wyoming-Dakota border, the stage failed to show up. They headed down the road in search of 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 would never make it, as on November 3, 1878, it was stopped by vigilantes who hanged Archie McLaughlin and another man named Billy Mansfield.
The next 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 afterwards, 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.