The American West: Charlie Siringo’s Cowboy Days

Charlie Siringo is best remembered for his years as a detective, undercover agent, and manhunter with the Pinkerton Agency, including his pursuit of Butch Cassidy and his accomplices in robbing trains. But Siringo was a cowboy before he was a Pinkerton detective.

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R.B. Miller

March 03, 20255 min read

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“Now, dear reader in bidding you adieu, will say: should you not be pleased with the substance of this book, I’ve got nothing to say in defence, as I gave you the best I had in my little shop, but before you criticise it from a literary standpoint, bear in mind that the writer had fits until he was ten years of age, and hasn’t fully recovered from the effects.”

Thus ended the autiobiography of one of the West’s great characters.

The subject of the book and its author—including that bit of humor—is Chas. (Charlie) A. Siringo. He is best remembered for his years as a detective, undercover agent, and manhunter with the Pinkerton Agency. His assignments ranged from Alaska to Mexico City, and he is credited with more than 100 arrests.

Siringo’s most famous Pinkerton case was most likely his pursuit of Butch Cassidy and his accomplices in robbing trains.

“I closed the Union Pacific train robbery case after having traveled more than 25,000 miles by rail, vehicles, afoot, and on horseback, and after being on the operation constantly for about four years,” Siringo said.

“The ‘Wild Bunch’ during these four years were pretty well scattered, many being put in their graves and others in prison,” he added.

Siringo wrote about his adventures as a Pinkerton man in A Cowboy Detective, which caused him untold grief with his former employer for violating confidentiality agreements even though much of the book was fictionalized to protect names and identities. He wrote other books as well in later years.

But the book that opened this story was written long before all that, and covers Siringo’s earlier life.

The autobiography carries an ambitious title, A Texas Cow Boy or, Fifteen Years on the Hurricane Deck of a Spanish Pony. Taken from Real Life by Chas. A. Siringo, an Old Stove Up “Cow Puncher” Who Has Spent Nearly Twenty Years on the Great Western Cattle Ranges.

The book was published in 1885, making its “Old Stove Up Cow Puncher” author, born in 1855, 30 years old.

Siringo spent his early years on the Matagorda Peninsula in Texas, then in St. Louis, and New Orleans for a time.

Raised by a single mother in dire poverty, Siringo was often on his own to fend for himself as a youngster. He returned to Texas in 1871 and hired on as a cowhand on Shanghai Pierce’s “Rancho Grande.”

The place “was considered one of the largest ranches in the whole state of Texas,” Siringo wrote. “To give you an idea of its size, will state, that the next year after I went to work we branded twenty-five thousand calves—that is, just in one season.”

When Rancho Grande was sold, the young cowboy worked at other ranches, and spent time branding mavericks, including applying his own brand to some, which made him “feel like a young cattle king.”

But he added, “The only trouble was they were scattered over too much wild territory and mixed up with so many other cattle. When a fellow branded a Mavrick in those days it was a question whether he would ever see or realize a nickel for it.” He did not, and spent most of his time broke and moving from job to job.

At one point, Siringo decided to give up the cowboy life and become a ship’s captain. As part of a questionable—downright criminal, truth be told—series of horse trades, he acquired a seagoing boat.

“Now kind reader you no doubt think that a shabby trick,” Siringo wrote of the horse trades. “If so, all I can say is ‘such is life in the far west.’ ”

He made a few voyages out into Matagorda Bay, acquiring melons which he sold upriver. His other schemes to haul freight failed, and he ended up abandoning the boat high and dry on the prairie following a failed attempt to haul it on rollers on a portage between rivers.

Siringo then “went to work again on my own hook, skinning cattle and branding Mavricks . . . . Cattle died pretty badly that winter and therefore I made quite a pile of money, besides branding a great many Mavricks.”

But the money was soon gone and Siringo was back to cowboy work, including driving herds north to Kansas, and acting as trail boss as he gained experience. He later spent a great deal of time wandering the wilds of New Mexico in search of cattle stolen from Texas ranches, where he crossed paths on occasion with the outlaw Billy the Kid.

Siringo’s book includes a chapter titled “A true sketch of ‘Billy the Kid’s’ life.”

In the final chapter, Siringo bosses a herd up the trail to Caldwell, Kansas, where he stayed for a time and purchased property.

Planning a return visit to Texas, he traveled to St. Louis to see his mother and sister for the first time in years. Back in the Lone Star State, he visited friends and family then returned to Caldwell.

In the midst of plans to go back to Texas and gather a herd to drive north, Siringo “fell head over heels in love with a pretty little fifteen-year old, black-eyed miss.” They were engaged three days after meeting, then it was off to Texas to bring up a herd of three thousand cattle.

A return trip was in the offing, but Siringo said he “suddenly swore off cow punching . . . . The next day I rented a vacant room on Main Street and, rolling up my sleeves and putting on a pair of suspenders, the first I had ever worn, started out as a merchant—on a six-bit scale. Thus one cow-puncher takes a sensible tumble and drops out of the ranks.”

But, as history shows, the tumble did not last. There were more Old West adventures in store for Charlie Siringo. But those are stories for another day.

R.B. Miller can be reached at WriterRodMiller@gmail.com

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R.B. Miller

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