Son of the Old West: The Odyssey of Charlie Siringo: Cowboy, Detective, Writer of the Wild Frontier, by Nathan Ward. New York: Atlantic Monthly Press, 2023, 347 pages,  $28 hardcover.

Charlie Siringo’s feelings about the Pinkerton National Detective Agency soured during the months in 1906 when, working for the agency, he guarded a confessed bomber. Harry Orchard was the star witness against the men charged with hiring him to do the dirty deed. Orchard had confessed to planting a bomb at the front gate of the house of former Idaho Gov. Frank Steunenberg, who died in the blast.

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Accused of ordering the hit were Big Bill Haywood and his associates George Pettibone and Charles Moyer, leaders of the Western Federation of Miners, a fast-growing union that would eventually morph into the International Workers of the World—the Wobblies. Haywood was tried first; representing him was the charismatic Clarence Darrow, who with this case would rise to national prominence as a champion of liberal causes. Listening in the crowded Boise courtroom to testimony day after day, Charlie found Darrow persuasive. Pinkerton agents had kidnapped the union men and managed their extralegal transport on a secret train from Colorado across Wyoming to Idaho. Charlie began to believe that Darrow was right—that, thanks to the Pinkertons, the men had been framed.

Charlie was just over 50 and had been working with the agency for 20 years. Bodyguarding a terrorist was more straightforward than most of the work. Normally, he posed as someone quite different from himself to win the confidence of criminals and get them, finally, to tell him things that would lead to their conviction. It was often months before Charlie acquired enough dirt to betray them. Several times, his betrayals very nearly got him killed.

He was a mustached, wiry little guy with a drooping Texas drawl. He was born in Texas in the 1850s to immigrant parents, his father Italian and his mother Irish. His father died when he was still small; it was a hardscrabble life and his mother made some unfortunate choices in subsequent husbands. Charlie left home. After the Civil War, Texas was full of millions of wild cattle with no market. Railroads pushing west across Kansas brought that market with them, however, and soon teenage Charlie was riding north with the trail herds.

By the time he was 23, in 1878, Charlie was working at the sprawling LX Ranch in the Texas panhandle. His boss sent him with others into New Mexico Territory to chase cattle stolen by young William Bonney—Billy the Kid—and associates. Charlie knew these guys, knew how to think like them and, after seven months, the posse returned with a herd of a few thousand. It was Charlie’s first taste of undercover work.

A few years later, he left the cowboy life for good, moved to Caldwell, Kansas near the Oklahoma line, traveled to the Texas gulf to retrieve his mother, returned, and opened a store. In Caldwell he met and married young Mamie Lloyd. Caldwell, writes Nathan Ward, was “the place where Charlie stopped being a cowboy and turned to writing about it.”

In 1885, Siringo published one of the best books ever written about cowboy life and certainly the most memorably titled: A Texas Cowboy or, Fifteen Years on the Deck of a Spanish Pony. The first edition sold out quickly. Confident he had a golden, literary life ahead, he moved with Mamie and their new daughter, Viola, to Chicago. 

But soon it was clear he’d need a steadier income. Four days after Mayday 1886, radicals bombed Chicago police during an outdoor labor meeting at Haymarket Square. Six police and four civilians were killed and many dozens more wounded. Charlie was horrified, walked into the Pinkerton office and talked the agency into hiring him. “It turned out,” Ward writes, “he was not just a cowboy author but a gifted character actor with all the skills he needed for his strange new job—to track, befriend, and betray.” For months on end, he lived in the skin of those characters—often Texans with a vague, shady past and yet funds from some unnamed benefactor that let him be saloon-generous with his targets. 

The work took him all over the West, befriending cattle thieves, mine salters and train robbers, sometimes with more success than others. He spent four years off and on following scattered leads left by Butch Cassidy and his Wild Bunch pals after the 1899 and 1900 Wilcox and Tipton robberies in Wyoming. But as early as 1891, infiltrating striking miners near Coeur d’Alene, Idaho, he found himself wondering if what he was doing was right. The work also kept him away from home a good deal. He was married four times. 

“The lie of a detective is a living lie, that is his business,” lawyer Darrow said at the Haywood trial. Charlie, who knew a detective’s life as well as anyone, agreed. Haywood was acquitted. Charlie resigned. He acquired a little ranch near Santa Fe, and again, struck out on a writing life. And he came out swinging. 

A Pinkerton’s Cowboy Detective: A True Story of Twenty-Two Years with Pinkerton’s National Detective Agency was still in galleys when the agency got a copy and went to court. When the book was finally published in 1912, it was milder. The names of clients, agents and the agency itself had been changed. The title became, simply, A Cowboy Detective. Nationally famous Pinkerton agent James McPartland became “McCartney,” “Pinkerton” was changed to “Dickenson” and Tom Horn became “Tim Corn.” 

Charlie took out a third mortgage on his ranch to publish a shorter, angrier book in 1915, the muckraking Two Evil Isms: Pinkertonism and Anarchism. This time, the agency got him charged with criminal libel but the governor of New Mexico, a friend of Charlie’s from the LX days, blocked extradition. Next, Charlie published an expanded version of his first book, titled now A Lone Star Cowboy, in 1919, a short life of Billy the Kid and a historical novel. But none of these books made a dent in his debts. 

In 1922, he sold what was left of the ranch and, suffering from lung trouble, moved to Hollywood. He lived for a time with Viola and later in a leaky cabin. He was welcomed, however, by a community of what Ward calls “cowboy exiles—” movie extras and stuntmen, who loved Charlie’s stories. Eventually, he became friends with Will Rogers and Bill Hart, the cowboy movie star. At long last he acquired a big-time publisher, Houghton Mifflin of Boston. The firm launched Riata and Spurs: The Story of a Lifetime in the Saddle as Cowboy and Detective, recycling much of the earlier material, at a big Hollywood party in 1926. A month later, the Pinkerton hammer came down yet again. The publisher caved, stopped sales and issued a version with all Pinkerton material removed and replaced by stories of outlaws Charlie had known, which he’d been planning to use in a subsequent book. 

He never wrote it. He died in Hollywood 1928. 

Charlie Siringo as Ward portrays him was a complicated, professionally dishonest and deeply likable man. Like many books of nonfiction about the West, this one is packed with action and anecdote. But it glances too at more important themes—ways the West came into many of the myths people here still live by; how one man’s conscience can survive decades of duplicity; how easily moneyed power can crush the livelihoods of any who oppose it.

To the end of his life, when Charlie signed copies of his bowdlerized editions, he would change “Dickenson” back to Pinkerton, and “Tim Corn” back to Tom Horn.

Read:

A Detective Gets His Man: The Capture of Rustler Clabe Young
Butch Cassidy in Wyoming
Tom Horn: Wyoming Enigma