The Cowboy as Detective: Finding Charlie Siringo’s West

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When Butch Cassidy and the Sundance Kid finally came to my boyhood mall, I saw it three times, wondering in the dark about the unnamed lawmen chasing the Wild Bunch outlaws around the West, the drumbeat of their horses’ hooves drawing Butch’s exasperated line, “Who are those guys?” One who chased the gang, I would learn, was a cowboy detective named Charles Siringo, who logged four years and 25,000 miles in pursuit. The film’s relentless riders can seem symbolic –standing for time running out on Butch and Sundance and their outlaw era or for the forces then changing the West itself. But it was for the pleasure of following along with one of the gang’s hunters, Siringo, that I later wrote Son of The Old West. 

I knew a couple of the Siringo books, but did not become interested in his story until I was researching a project on Dashiell Hammett’s transition from young Pinkerton operative to crime writer, The Lost Detective, in the Pinkerton archive at the Library of Congress. The Pinkerton archive is a self-selected trove of wanted posters, cypher code books, operative reports, forensic drawings, and crime scene photos. The Pinkertons donated it primarily to highlight some of their earlier triumphs and counter their later reputation for anti-union work. It is a fantastic collection, no matter its original purpose.

The name Dashiell Hammett did not appear in those Pinkerton files. But that of Charles Siringo repeatedly did, both for his heroics infiltrating the Wild Bunch and other desperado gangs but also in the agency’s repeated lawsuits to squelch the books Siringo kept publishing about his undercover adventures. There were several files devoted to Pinkerton’s court cases against him, yet he kept telling his story in the face of ruinous lawsuits, as if his life was too interesting not to write about, no matter what contract he had once signed. His stubbornness was intriguing. I copied much of the Siringo Pinkerton materials, and later, when the Library of Congress shut down for the pandemic, had a stash of research squirreled away.

Siringo’s story illustrates the history of the Old West he saw, from the cattle trail days and the birth of the railway cow town to outlaw times and early Hollywood; encountering everyone from the southwestern outlaw Billy the Kid to Comanche leader Quanah Parker, even brawling with Buffalo hunters one night in Bat Masterson’s Dodge City saloon. Because he spent two decades undercover, playing rough frontier types, outdrinking and outwitting the criminals he befriended and betrayed, Siringo’s actual character has not become fixed in the popular mind. He went everywhere in the West, but often under different names. So who was he? 

Cowboy

Born in Matagorda, Texas in 1855, Charlie was already an author when he signed with the Pinkertons. The year he turned thirty, he published A Texas Cowboy: Or, Fifteen Years on the Hurricane Deck of a Spanish Pony (1885), about the life he had just left behind and the open range that was disappearing behind barbed wire. He had never written a book before. In fact, no cowboy had published an autobiography; their literature did not yet exist. It is by far his freest and most joyful work to read, and ends with Charlie giving up the cowboy life, donning “a pair of suspenders, the first I had ever worn” and becoming a Kansas merchant:

Thus one cow-puncher takes a sensible tumble and drops out of the ranks. Now, dear reader in bidding you adieu, I will say: Should you not be pleased with the substance of this book, I’ve got nothing to say in defense, as I gave you the best I had in my little shop…

Published the same year as Mark Twain’s The Adventures of Huckleberry Finn, which fashioned a national literature out of American dialect, Siringo’s book committed frontier speech and cowboy culture to the written page. Will Rogers would call it the “Cowboy’s bible.” 

Siringo improved some true events he had not seen first-hand, such as claiming to sneak aboard the steamboat Robert E. Lee in time for its famous race against the Natchez in the summer of 1870; or, despite being in the next town, giving a cinematic description of the lynching of city marshal Henry Brown (whom he knew was at heart an outlaw) after he failed to rob the Medicine Lodge Bank in 1884.

But Charlie tells it straight when it comes to events like getting shot himself, fired upon by a hired gunman in April 1875: while he was smoking by the fire of his skinning camp one evening near Cashs Creek in Matagorda County, Sam Grant, a Black cowboy and sometime killer, rode up, aimed his Colt Dragoon at Siringo’s heart, and pulled the trigger. Sitting with his leg still drawn up, level with his heart, the pistol ball entered Charlie’s kneecap instead of his chest. A Black cowhand friend known as Lige came riding suddenly through the trees, and Grant pretended to have fired by accident, then rode off, pledging to send back the doctor from miles away at Deming’s Bridge. Dr. A. M. Pelton was able to reach him by sunrise to remove the ball, and save Siringo’s knee. In Hollywood decades later, the retired physician read an article about Charlie in the Los Angeles Times and invited him for a reunion, where they reminisced about Pelton’s removing the ball. (Siringo inscribed his thanks in a copy of one of his books that recently turned up online: “To my dear old-time friend, Dr. A.M. Pelton, the surgeon who rode 25 miles between midnight and daylight…to cut a bullet out of my body…”) 

Detective

A blind old phrenologist had once laid his hands on Charlie’s skull in a hotel lobby in Caldwell, Kansas, pronouncing him fit only to be a stock rancher, newspaper editor, or detective. But it was only after moving his family from Kansas to Chicago in 1886 that Siringo joined Pinkerton’s National Detective Agency, driven to fight anarchists, he said, by the city’s Haymarket bombings. The company sent him to its new Denver office to become a cowboy detective on dozens of missions across the West—a bold and chatty little mustached Texan, with cowboy skills to match his gift for making friends, drinking with rough characters or flirting with the sisters and girlfriends of wanted men to learn their whereabouts. On the wide-ranging Wild Bunch hunt, he would romance both the Mormon sister of Butch Cassidy and Lonnie Logan’s common-law wife, Ellie, reading her letters and learning “all of her secrets.” Entering each troubled town asking the agency’s help, Charlie’s favorite role was the cowboy fleeing mysterious trouble, buying rounds to seal desperado friendships:

In Fairplay [Co.], two tough dance-halls were running, and night was turned to day by the tough element. Of course, I joined them, and I was to play the part of a Texas outlaw.

In his undercover stories, Charlie would arrive at a stranger’s ranch and offer to break his meanest bronc, knowing the spectacle might bring a crowd including the wanted man thought to be hiding on the premises; or he would gentle the skittish horse of a criminal he was trying to befriend in town. Such seemingly implausible tales were well within Charlie’s skill set, as shown when he competed in a cowboy contest in Denver in 1887, combining his old cowboy life with his sleuthing profession while appearing under his sometime literary alias, ‘Dull Knife’: Charlie was not going to miss out on a cowboy contest in the town where he lived as a detective, even if he had to compete as someone else, and the Rocky Mountain News noted that ‘Dull Knife’ in his sombrero was “such a perfect and graceful type of a Texan cowboy that the audience gave one spontaneous A-h-h-h! of admiration.”

A dramatic train robbery of the Union Pacific railway near Wilcox, Wyoming, on June 2, 1899, inspired William Pinkerton to dispatch his two best cowboy detectives, W.O. “Billy” Sayles and his sometime partner Siringo, on a quest that lasted much of four years and ranged all over the West. Members of the train robbing gang, which included Butch Cassidy, Ben “Tall Texan” Kilpatrick, Harvey Logan (‘Kid Curry’), George ‘News’ Carver, and Harry Longabaugh (the Sundance Kid), hit the UP railway again the following year at Tipton, Wyoming. Just as in the famous movie, they were met by the same brave express messenger who had survived their dynamiting of his rail car at Wilcox, George Woodcock, who this time listened to reason and emerged just before they blew the safe.

After the Tipton robbery, Charlie rode out to interview the owner of a haystack in southern Utah, where Kid Curry and some comrades from the Union Pacific robbery had slept. Then he “drifted over to Indian Creek, a place noted for tough characters, and got in solid with an outlaw named ‘Peg Leg.’”  In Utah’s San Juan County, ‘Peg Leg’ showed him “a high mountain ridge” from which he could see much of the landscape of the Wild Bunch. He eventually followed the gang to Alma, New Mexico, where Butch Cassidy and others worked on a ranch under assumed names; he visited the Alma saloon where Butch also tended bar as ‘Jim Lowe,’ but Butch had skipped town and ultimately fled the country with the Sundance Kid, dying together under Bolivian soldiers’ bullets in 1908.

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After two decades learning about “human nature” as a Pinkerton, Charlie retired in 1907, beginning work on what became A Cowboy Detective, “an autobiography of many thrilling adventures, on mountain and plain, among moonshiners, cattle thieves, tramps, dynamiters, and strong-arm men.” His manuscript quickly attracted the attention of the agency’s lawyers; especially the sections where he named clients and revealed company methods. 

A box at the Library of Congress holds a galley for what was called A Pinkerton’s Cowboy Detective: A True Story of Twenty-Two Years with Pinkerton’s National Detective Agency, marked up with blue pencil, underlining the many passages found objectionable by the agency in seeking an injunction against its author. The Pinkertons held up publication for two years with legal challenges redacting and replacing names, even the word ‘Pinkerton’ ultimately became ‘Dickenson.’  (A number of the book’s aliases have made their way into Western history books.) 

Despite its changes, the book remained authentic enough to influence hard-boiled writers: 

The body was in good shape, with the exception of the right hand being cut off. The hand was never found, and here hangs a tale. 

A Cowboy Detective inspired Dashiell Hammett in writing his 1925 crime story “Corkscrew,” in which his stocky urban Continental Op is sent to investigate some murders of Arizona cowboys and is thrown repeatedly from a devilish horse to gain acceptance. (The Op, a city man, asks the cowboys for a mild mount and of course receives the opposite, proving his worth by gamely taking his beating being thrown.) If the hard-boiled American detective fiction of the 1920s was largely the classic cowboy story adapted to a city setting, then Siringo had carried it there from the Texas plains. Certainly he would have recognized the Western world of Hammett’s novel Red Harvest, with its Montana mining town that’s part Butte, part Anaconda. As a detective, Charlie had entered many towns held hostage by thuggish elements and was often saved by his cowboy training; he wrote about both lives, bridging one to the other.

Wild as they sometimes seem, Siringo’s detecting narratives were often delivered under oath in court. To investigate a dynamiting ring in Tuscarora, Nevada, he was hired in a San Francisco hotel by one of the survivors from an explosion in April 1889: two executives from the Price and Peltier mining corporation had just retired for the night to their separate cabins in the mining camp of Tuscarora when they suffered simultaneous bombings. Long fuses were lit that touched off blasting powder beneath each of their beds, blowing the men through their own roofs. George Peltier had been tucked in his blankets before the bomb threw him into the air, landing on his mattress in the street, and was able to recover surprisingly quickly. But C. W. Price had not been as well tucked when the charge went off, and landed hard on the roadbed, his wounds considerable. Siringo went to work at the mine and befriended a dynamiting suspect among the miners whom he brought on an epic prospecting trip into the Wichita Mountains until he confessed his crime one night beneath the stars.

During the mining wars in the Coeur d’Alenes, Siringo secured a job in Gem, Idaho as a union recording secretary until his cover as C. Leon Allison was blown, in July 1891. A mob of angry miners next came for him at his boarding house, where Siringo hid beneath the floorboards of the first floor, then crawled toward the street, inching along on his belly under the wooden boardwalk where the armed mob was waiting. After his dangerous months as a miner he returned wearing a sharp suit to a Boise courthouse in 1892, his testimony convincing enough that the defense chose not to cross-examine. Siringo later claimed to regret his anti-union work, but remained proud to the end of his crawl to freedom. After his boarding house later burned down, it pained him to know “the hole sawed in the floor went up in smoke” and could not be “handed down to my grandchildren as a relic…”

Hollywood 

There was a price for living so long among outlaws. Debt and failing health finally forced him to give up his ranch outside Santa Fe and resettle in Los Angeles in 1923. Moving to a bungalow in Hollywood, he sold his books out of a satchel and fell in with a group of admiring Western writers and film people, including the silent film star William S. Hart, who hired him to advise on his final movie, Tumbleweeds, in which Charlie appeared briefly in a saloon based on his own recollections of Caldwell, Kansas.

One of Siringo’s literary friends recommended him to his own publisher, Houghton Mifflin, which agreed to publish a last memoir, covering the ground of Siringo’s earlier Western books, without masking names. Riata & Spurs received a terrific reception from newspapers across the country in 1927, one calling him “Ulysses of the Wild West.” But Pinkerton’s lawyers were ready once again: finding themselves under legal attack, his Houghton editors removed scores of pages of his Pinkerton adventures. (The book’s short-lived first edition contains the real names changed or excised from A Cowboy Detective, and surviving copies make a useful key for reading his other books.) 

Siringo died the next year, 1928, and was buried in Hollywood. Asked once as an old man if he had led a brave life, he answered simply, “I was a plain damn fool, that’s all.”  Charlie was never a gunfighter, yet in Western dramas since his death he often appears (played by Steve Forrest, Dennis Farina, or Cole Hauser) as a gun-happy manhunter, embodying the notoriety of his longtime employer, Pinkerton’s. In the Arthur Penn Western The Missouri Breaks (1976), a Montana horse rustler played by Jack Nicholson nervously robs a train, boasting to the express agent that he is Jesse James himself. “You ain’t Jesse James,” sneers the agent, and Nicholson answers, “Well, you ain’t Charlie Siringo.”

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Son of the Old West was written largely during the pandemic: as people brought puppies home to lift their spirits, a 165-year-old bowlegged stranger moved into our house, along with all his books,  clanking around and talking mainly about himself and his favorite horses; showing off his ‘old Colts 45’ or snaring bed posts with long tosses of his riata; while also spinning charming, if sometimes contradictory yarns about the frontier he had known. It is a pleasure finally to send him back out on the trail he loved. 

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