Two detectives came out to Wyoming in early February 1885, seeking a boy from New York City and the ten thousand dollar reward posted by his father. The boy, an eleven-year-old banker’s son named Fred Shephard, had disappeared the month before, but had not been abducted. An obsessive reader of Western dime novels, the young man broke open his tin bank one January night and climbed down the rain spout from his room to the street. His latest book was left at school, his heroic intentions scrawled across the bottom of its open page, “Ime goin West to be a cowboy detective.”

“It is the old story of novel reading,” wrote a reporter for the Cheyenne Leader when the detectives arrived, their strongest clues being in the boy’s book collection. After conducting interviews, the pair split up to search wide swaths of Texas and Arizona, but young Fred was gone, unprepared by tenderfoot writers for the West into which he vanished.

Readers who’d never been west of Hoboken nevertheless learned to lionize distant frontier figures and their murky violence: After the shooting death of Billy the Kid in 1881, a jar turned up in New York said to contain the outlaw’s trigger finger with which he had dispatched anywhere from eight to twenty men around the Southwest. People paid to see the floating finger on the chance it originated on their young hero’s hand; the Kid’s alleged skeleton also went on tour, drawing true believers as well as the ghoulishly curious and editorials worried about “bogus Billies”: “[W]orshippers of the hero,” cautioned Nashville’s Tennessean, “can never know of a verity that they are not paying for a sight at some ninny who never murdered a man in his life—some soft person from the East, may be, and even, perhaps, some Sunday-school superintendent.” No part of the Kid seemed to have remained buried, despite the angry denials of the man who’d put Billy in the ground, Sheriff Pat Garrett.

The gap between myth and reality could be deadly in the West, where many learned the dangers of dime novels. An Eastern liquor salesman arrived in Helena, Montana in 1879, tragically ignorant of the current gunfighter fashion to keep revolvers in the hip-pocket. He was standing and having a drink, reported one San Francisco newspaper, but as the salesman reached down to retrieve his handkerchief from his pants, “The saloon keeper grabbed a pistol from under the bar, and the drummer was gathered to his fathers.”

Article continues after advertisement

Among the Vigilantes

It was from Mark Twain’s great book about the West, Roughing It, that I first learned of the strange career of Thomas Dimsdale. Riding an Overland coach in the Black Hills in 1861, Twain’s group of passengers had been on nervous watch for Indian attack when they instead overheard their stage driver being loudly killed one night by unseen ruffians. The stage moved on without its murdered driver, and Twain heard anxious talk from strangers along the route about an infamous road agent named J. A. Slade. He became fascinated: “Day or night, I stood always ready to drop any subject in hand, to listen to something new about Slade and his ghastly exploits.”

Twain later read Slade’s life and execution described in a “bloodthirstily interesting” book about vigilantes in Montana, written by a “Prof. Thomas J. Dimsdale.” It would be just like Twain to satirically invent and impersonate his own expert professor, especially one who writes as elegantly as Dimsdale, whom Twain quotes at length:

“While on the road, Slade held absolute sway. He would ride down to a station, get into a quarrel, turn the house out of windows, and maltreat the occupants most cruelly. The unfortunates had no means of redress, and were compelled to recuperate as best they could. On one of these occasions, it is said he killed the father of the fine little half-breed boy Jemmy, whom he adopted, and who lived with his widow after his execution.”

It turned out both Dimsdale and his vigilante book were real. When I found my own copy (at the Grizzly Claw general store in Seeley Lake, Montana), it was every bit as “bloodthirstily interesting” as Twain had promised.

A bookish man in frail health from a lung ailment, Thomas Dimsdale had come from Canada to the rough gold-mining town of Virginia City, in the Montana Territory, probably in 1863. A learned, English-born newcomer, he became a schoolmaster, a Mason, and an editor of the Montana Post—the territory’s first newspaper—hanging Shakespearean quotes on any grim frontier story that needed elevating. Mining towns were a lusty mixture of hard-working miners, bartenders, dancehall girls and prostitutes, largely governed by what Dimsdale called the “mountain code” of behavior. But a number of murders and robberies by road agents led in 1863 to the formation of a town Vigilance Committee, sworn to “kill or be killed.” Dimsdale somehow became its historian, if not one of the vigilantes himself. It is possible he had no say in the matter.

Article continues after advertisement

Many of his accounts—of highwaymen righteously dispatched, or of the supposed crimes of Sheriff Henry Plummer—ran first in his newspaper. Sheriff Plummer, whether or not he lived the secret murderous life of a highwayman as the Committee charged, was eventually executed by them, joining the notorious J. A. Slade. Dimsdale put the Committee’s work in a fine pious light, such as the group’s capture of Bill Hunter:

“The escorts proceeded on their way homewards for about two miles, and halted at the foot of a tree which seemed as if it had been fashioned by nature for a gallows….Scraping away about a foot of snow, they camped, lit a fire, and prepared their breakfast.

After eating, the men voted to hang Hunter on the spot rather than return him to town, throwing the rope over the well-shaped tree limb and placing the noose on the prisoner:

“the men took hold and with a quick, strong pull, ran him off his feet. He died almost without a struggle; but, strange to say, he reached as if for his pistol, and went through the pantomime of cocking and discharging his revolver six times….Everyone present saw it, and was equally convinced of the fact. It was a singular instance of ‘the ruling passion, strong in death.’”

Dimsdale framed the death spasms of a hanged man with a line from Alexander Pope to show he had evil in his heart and so deserved what they’d done to him. The very quality of his descriptions begs an interesting question: Was he simply a highly literate witness or was he drafted by the Committee to become their vigilante correspondent? If he felt a moral twinge about the Committee’s violent work, he did not record it.

Vigilantes of Montana is one of those few books that somehow retains its authority despite the writer being too close to the story. Dimsdale presents one of the best witness portraits published of life in a 19th-century mining camp, and provides a wallflower’s excellent observations of a “Hurdy-Gurdy” dance, where armed and bearded “mountaineers” in buckskin leggings pay gold to dance with women in white gloves and scarlet dresses.

Article continues after advertisement

For decades, Dimsdale’s history was accepted as a partisan but reliable witness account. But some recent Western scholars (including R.E. Mather) have questioned the truth behind Sheriff Plummer’s alleged crimes, and wondered about Dimsdale’s intimacy with the citizens who executed the Sheriff. No doubt the book’s high prose polish helped it gain acceptance. Always in frail health, Dimsdale died in September 1866, while finishing the foreword to his dark, lucid book.

Billy’s Bones

Driven mainly by the posthumous rumors by Billy partisans and East Coast writers that he had killed the Kid in a “cowardly” manner undeserving of their hero, Sheriff Pat Garrett undertook The Authentic Life of Billy the Kid (1882). Written with his journalist friend Ash Upson, much of the book adopts a breezy 19th-century newspapering voice. But Garrett’s narrative bides its time, rehearsing much of the familiar lore of the Kid’s outlaw career, the many altercations in which the short-tempered “defender of the helpless” supposedly had no choice but to steal or kill. Garrett obeys the parameters of the Billy myth to lead the worshippers along a respectful path long enough to have their full attention to show them his just execution in that New Mexican house.

Garrett gets to the genuine point on page 139, when the narrative abruptly switches to a steely, first-person manhunt story leading up to the precisely drawn final nighttime showdown. “As it would be awkward to speak of myself in the third person throughout the rest of this narrative,” our surprise narrator suddenly explains, “I shall run the risk of being deemed egotistical and use the first person.” To kill the Kid, someone flesh-and-blood with specific skills is needed, not some Olympian storytelling device. Everything that follows from here on the Sheriff saw for himself—how many desert miles chased on horseback, the number of Winchester shots traded, the dimensions of the outlaw’s cave hideouts. Once the hunt commences it drives straight through until the fatal night with Garrett waiting in the dark bedroom, where the barefoot outlaw burst in holding a revolver and a butcher knife and demanding “Quien es?”(Who is there?). With a shot to the heart Garrett insured “the Kid was with his many victims.”

All books on William Bonney have problems—either from trafficking entirely in Robin Hood-like lore, or hampered by the dearth of actual biographical information. In many ways, Billy is the least interesting of our outlaws—not still killing and thieving for the Lost Cause like Jesse James; not driven to best his criminal cousins like the Daltons. Instead, this book deserves to be read for the Sheriff’s firsthand story that brings it home, especially this year with Ethan Hawke playing Pat Garrett in ‘The Kid.’

Article continues after advertisement

Cowboy Detective

Real cowboy detectives were every bit as skilled and cool under fire as the fictional ones young Fred Shephard had left home hoping to become in 1885. The most famous of them, Charlie Siringo, joined Pinkerton’s the year after Shephard’s disappearance. When he joined the agency, Siringo was already a bestselling author of the first published cowboy autobiography (A Texas Cowboy: or, Fifteen Years on the Hurricane Deck of a Spanish Pony). He then worked for twenty-two years as a Pinkerton detective, largely undercover. Betrayal became his business, tracking and befriending outlaws, infiltrating their gangs under a series of names—C. Leon Allison, Leon Carrier, Dull Knife, or Charles T. LeRoy—posing as a tramp in the Mojave or a Colorado silver thief, a machine oiler in a gold mill, a bronco buster, mining executive, union radical or cowboy fleeing the law.

He spent many nights intentionally jailed with train robbers or ore thieves in order to draw out late-night confessions and had even chased Kid Curry and the Wild Bunch for twenty-five thousand miles. (Flirting with Butch Cassidy’s sister, he learned the outlaw’s last known whereabouts as well as Butch’s surprising childhood nickname, “Sallie.”) While undercover as a union spy in Cripple Creek, Colorado a detective from a rival agency had given him up to the miners, who planned to throw Siringo down an abandoned shaft when a dance hall girl warned him who “couldn’t believe me degraded enough to be a detective.”

After he retired from Pinkerton’s in 1907, Siringo assumed he would return to writing, and wrote up all his favorite frontier cases living among the outlaws and later working as a Western labor spy. But the agency stepped in and challenged his right to his adventures, forcing him to change almost every professional name, including that of Pinkerton’s itself, substituting the fictional ‘Dickenson’ Agency. The result was A Cowboy Detective, which was held up and reworked for two years, but is still a wonderful portrait of the life of a detective drifting the West undercover “playing outlaw.” (Pinkerton’s was less concerned about the feelings of grifters and desperados Siringo had thrown to the law, and they mostly appear correctly.) The book shows the West gradually changing with the job itself, as the land and company come more under the influence of corporations. By the time Siringo is chasing the last of the West’s great train robber gangs, the Wild Bunch, no one wants the era to end.

Siringo lost money on his legal battles over A Cowboy Detective, but could not stop from writing his autobiography twice more before his death, challenged by Pinkerton’s to protect its secrets to the end of his life. (To correct all the agency’s name changes in Cowboy Detective, you can check it against the rare first edition of his final book, Riata & Spurs, another fine portrait of the frontier, for which he was sued a final time in 1927.) It seems the incredible life was more than worth the trouble, though. “In closing my twenty-two years of experience in studying human nature,” Siringo sums up his detecting days, “I have come to the conclusion that there is more good than bad in Mankind.” As A Cowboy Detective shows, he sifted through a lot of the bad characters of the West to reach his judgment, and had a kind word for most.

Article continues after advertisement

Last Ride

When the Dalton gang rode into Coffeyville, Kansas on October 5, 1892, it was a fatal act of outlaw hubris: robbing two banks at once, something Jesse James himself had never done, and in the town where they once had lived as boys. Instead of accomplishing a double-heist, though, they were shot down by townspeople, almost none of whom was armed when the gang rode into town that morning. The locals may have lacked guns, but they got them off the racks at the town’s two hardware stores and took aim from the upstairs windows of one, Isham’s, with a good view of the Conlon bank. David Stewart Elliott, editor of the Coffeyville Journal, had a pretty good vantage point himself:

“The moment that Grat Dalton and his companions…left the bank that they had just looted, they came under the guns of the men in Isham’s store. Grat Dalton and Bill Powers each received mortal wounds before they had retreated twenty steps. The dust was seen to fly from their clothes…”

Elliott, a veteran of two Pennsylvania Union regiments, was known to the Dalton boys for having once done a divorce proceeding for their mother. Disguised uselessly with false whiskers, they shouted to each other to spare “Colonel Elliott” in the initial shooting. But he wrote after the battle was over in roughly twelve minutes,“The notorious leader of the Dalton gang….staggered across the alley and sat down on a pile of dressed curbstones near the city jail.” The youngest of the gang, 19-year-old Emmett Dalton, was shotgunned off his horse as he tried to carry a sack of money in one broken arm and reach the other down to his prone brother Bob. Four townspeople and four robbers died in the battle, and young Emmett Dalton survived, with over twenty wounds, although he was listed with the dead in the evening editions.

Within weeks of the showdown, editor Elliott had a commemorative booklet out, Last Raid of the Daltons: a Reliable Recital of the Battle with the Bandits, featuring a Homeric account of the battle and engraved portraits of all the principals, dead and living, good and bad. (The reprint by the Coffeyville Historical Museum can still be purchased online). It remains the finest brief account of the battle and its significance.

Emmett Dalton, lone survivor of the gang, was a model prisoner and later wrote his own confessions twice, in two different moods about his past. The first, Beyond the Law (1918), shows the proper contrition of a former prisoner and sounds closer to the way I imagine he actually talked, especially when he recounts the events at Coffeyville, shot as he reached down for his dying brother’s hand.

Article continues after advertisement

The second autobiography, When the Daltons Rode (1931), was jealously written during the Depression craze for gangsters (Dillinger, Pretty Boy Floyd, Al Capone). It is more openly romantic about his former life with his criminal brothers and about the American “cult of the rogue.” It shows the influence of his reporter collaborator, but also has the benefit of time, especially when writing about the difference between border outlaws of the old West and modern gangsters with bodyguards prowling in touring cars: Having long endured the bloody fictions about the Daltons in “yellow-backed novels,” he scorned the gunfighter tropes he saw in Western movies set in the time when he rode with his outlaw brothers: “Never did I see a man ‘fan’ his six-shooter,” he explains. “Never did I see any shooting from the hip. Never did I see a man waste precious ammunition by using two guns simultaneously.” And certainly no “bad man” worth his salt had ever notched his gun in Emmett’s presence. As for his big brother Bob, “accounted one of the best shots in the Southwest,” he writes, “Never once did he indulge in any of the phony stunts attributed to so many ‘master’ gunmen of the border.”

That was all dime novel stuff, as the West Coast newspaperman Allen Kelly had pointed out as far back as 1889, not long after an enraged man named Bob Sinclair had tried what the yarn writers called “fanning the hammer” of his pistol in attacking Jack Riley in Albuquerque. “There is no doubt Mr. Sinclair made a great deal of noise in a very short time,” Kelly, a hunting columnist, skeptically reported: Sinclair’s “fusillade” hit a carpenter shingling a roof, broke a mirror inside a saloon, scattered an outdoor card game and shot his own left foot, while his two other bullets “escaped in the confusion, and are still at large.” But when the smoke had cleared, Jack Riley still stood, surprised but untouched. It was then, Kelley noted, that “Mr. Riley picked up a board and swatted Mr. Sinclair on the ear.”