Editor’s note: This is the second of a two part series.


Texas native Charlie Siringo enjoyed a career in law that took him across the country, leading to adventures with some of the most noted names of the Old West. His years took him from cattle drives across Texas to chasing down Billy the Kid in the New Mexico Territory. His clever undercover techniques helped him capture dozens of some of the most wanted dangerous outlaws on the frontier. With more than 20 years with the Pinkerton Detective Agency, Siringo tangled through some of the most chaotic chapters in the history of the West.


By the late 1890s, Butch Cassidy and his Wild Bunch gang had committed a string of armed robberies in Wyoming, Colorado, and Utah. Cassidy joined forces with Harry Longabaugh, also known as the Sundance Kid, in 1897. After two dramatic, highly-publicized train robberies in the summer of 1899 in Wyoming and the New Mexico Territory, the Pinkertons assigned Siringo and several others to bring them in.


The Wild Bunch Gang had already killed several people in shootouts, and Siringo knew he could not take them head-on. Siringo instead went undercover, posing as a murderer on the run, and joined the Wild Bunch, carefully collecting information along the way. He rode with the gang for a year through the mountains and desert plains. He sent information to other Pinkerton operatives and lawmen, leading to the arrest of several members of the Wild Bunch. Before Cassidy and Sundance knew what was happening, their gang was falling apart. Siringo had so successfully disrupted their operation that the gang fled to Texas before breaking up in 1901. Butch Cassidy and the Sundance Kid then fled to Bolivia and into legend.


After apprehending several other outlaws in his travels, Siringo was back in Colorado in 1903. Once again, Siringo found himself undercover with a mining union as the Colorado Labor Wars erupted. Contract disputes had escalated into open gunfights between miners and owners. The Colorado National Guard had declared martial law in response. Owners hired the Pinkertons to protect their interests at all costs. Violence grew even worse after the state ignored a new law mandating miners work no more than eight hours daily. Siringo again supplied intelligence on union activities. He later revealed how mine owners also forced him to rig the balloting in the vicious 1904 Colorado gubernatorial race. In his memoirs, he later called his activities in Colorado “a dark blot on my conscience.”


Siringo retired from the Pinkertons in 1907 at age 52. His dogged determination and innovative undercover techniques resulted in his arresting more than one hundred criminals in his career and gaining a respected reputation across the country.


The agency, however, refused to let go of Siringo. They would pursue him for the rest of his life as he tried to publish his stories. He wrote three books on his time with the Pinkertons, which each facing protracted court action. Pinkerton agents went so far as to buy every available copy of the books to make sure they would not get into circulation.


In 1916 at age 61, Siringo briefly served as a New Mexico Ranger, riding through the drylands and sharp ravines in pursuit of cattle thieves and bandits. Two years later, he could no longer keep up the unforgiving pace of a Ranger, and his faltering finances led him to retire from ranching as well. He moved to California and met up with his old friend Wyatt Earp. The two aging gunmen soon became celebrities in Los Angeles as they charmed actors and starlets with their tales of the Old West. In 1927, Siringo once again published a book of his exploits, Riata and Spurs, only to again have the Pinkertons try to block its publication. After several months of legal wranglings, the book was finally published as a watered-down and fictionalized series of tales. He died quietly at his home just outside Los Angeles in 1928 at the age of 73, just three months before Earp.


Their deaths effectively closed the door to the whirlwind early days of the West. Siringo continued to be remembered long afterward, often referred to in modern western novels and movies. The City of Santa Fe named a street for him, and a TV movie about his life appeared in 1994.


Ken Bridges is a Texas native, writer and history professor. He can be reached at drkenbridges@gmail.com.