Were Pinkerton Agents Violent Enforcers for Capitalism or Virtuous Protectors of American Values?

Diptych of real Pinkerton agents and the ones in Red Dead Redemption

An illustration from Harper’s Weekly, v. 36, and a screen from Red Dead Redemption 2.

Photo illustration by Slate. Illustrations by W.P. Snyder after a photograph by Dabbs, Pittsburg/Library of Congress and Rockstar Games.

The first time Arthur Morgan, the outlaw protagonist of the popular video game Red Dead Redemption 2, meets Pinkerton agents Milton and Ross is in one of the game’s cut scenes. The two agents, employees of a fictionalized version of the historical Pinkerton National Detective Agency, break into the pastoral calm of Morgan’s fishing expedition with the young child of a fellow gang member. Agent Milton is pockmarked and sinister, and the actor (John Hickok) delivers his lines in a hammed-up, insinuating tone; he might as well be twirling his mustache. Red Dead 2 has multiple antagonists—the leader of Morgan’s gang, Dutch van der Linde, is slowly morphing from a utopian thinker and rescuer of orphans into a cruel and greedy killer—but the Pinkertons, and Agent Milton in particular, are the game’s stock villains.

The present-day Pinkertons noticed the depiction, and took offense. In December, the 167-year-old company, now owned by the Swedish security firm Securitas AB and called Pinkerton Consulting and Investigations Inc., sent a cease-and-desist letter to Take-Two Interactive Software Inc., owner of Rockstar Games, the creator of Red Dead 2, requesting some form of royalties for the use of its trademark. Take-Two filed suit in response on Jan. 11, asking that the Pinkerton trademark should be declared fair use. In its request for declaratory judgment, Take-Two argued: “Defendants cannot use trademark law to own the past.” (Reached for comment, Take-Two declined to speak further on the matter, citing pending litigation.)

The court will ultimately have the last word, but the conflict does seem, at first blush, to be somewhat ridiculous: How many times have we seen Pinkertons in popular entertainment, from Deadwood to Boardwalk Empire to BioShock Infinite? And that’s only the fictional Pinkertons that have surfaced in recent years. The agency has a long “Appearances in popular media” Wikipedia section, and at least one historian, S. Paul O’Hara, has written an entire book on the agency’s evolving significance in public culture. Aren’t “The Pinkertons” ours now, part of our popular culture, to do with as we please?

Today’s Pinkertons don’t see it that way. When we spoke about the situation, the company’s president, Jack Zahran, emphasized the harm he felt the game had done to the company’s historical reputation, rather than the company’s request for royalties for the use of its trademark. Zahran asked me, “Is it open season on companies that have achieved longevity? What’s next? A game where Coca-Cola poisons mankind?” This conflict about the nature of the Pinkertons’ cultural reputation—is it public record? Or a matter of commerce?—is all too appropriate. Throughout the company’s history, Pinkerton has provoked passionate disagreements about the relationship between public and private, capitalism and the state. And in 2019, these matters are far from resolved.

The Pinkertons first filled a niche in the market while the rapidly growing United States tried to figure out what it wanted to do about policing. In the second half of the 19th century, Americans were moving across great expanses of space in the West, but had not come to agreement regarding who should be responsible for enforcing laws in the middle of nowhere. This made capitalists, who were trying to make money in the “Wild” West, very nervous. The answer to this problem, for decades, was that those who could pay could buy security for their property and their interests, in the form of Pinkertons.

The Pinkerton National Detective Agency, founded by Scottish immigrant Allan Pinkerton in the early 1850s, initially found work by offering employers a way to identify employees who might be costing the company money. Railroads were some of Allan Pinkerton’s first and best customers. Pinkerton spies tried to ferret out conductors who, on their long shifts between stations, were operating unsupervised and might sleep the hours away, or chit-chat with passengers, rather than carrying out their duties. Conductors could also pocket the money from tickets they took on the trains, and the people in charge would be none the wiser. It was as early as this phase in the company’s history that workingmen began to resent Pinkerton’s presence. “Pinkerton operatives were called ‘vipers,’ ‘spies,’ ‘scoundrels,’ ‘jailbirds,’ and ‘thieves set to catch a thief,’ ” Frank Morn writes in his history of the agency, “The Eye That Never Sleeps”.

The Pinkertons first filled a niche in the market while the rapidly growing United States tried to figure out what it wanted to do about policing.

But Red Dead’s Pinkertons aren’t passing on names of embezzlers and malingerers to bosses. They are finding a bandit gang and bringing them to justice, and in the 1860s, this was how the agency burnished its name in the public eye. Pinkertons, Morn writes, had 10 years of “successful and glamorous detection of railroad bandits” after the Civil War. Morn takes the fact that local vigilantes lynched the members of two gangs the Pinkertons busted, the Reno Gang and the Farrington Brothers, as evidence that in identifying railway bandits, the Pinkertons’ actions generally aligned with the desires of the local populace.

This is the argument Zahran made to me as well—that people in the West wanted the Pinkertons, who were paid by the railways, banks, and express companies who lost money to outlaws, to bring the gangs to justice. “Good people who were trying to build a life for themselves and to build a home under harsh conditions. …What the bandits actually did was come in, murder you and your family, take your property, and say ‘this is mine now,’ ” Zahran said. “If you think of the foundation of rule of law and trust and the foundation of our economy, it’s all predicated on the confidence and trust that you can transact and have property rights and personal rights. … That’s the origin of what we were up to, we believe.”

And in some corners of popular culture in the 1860s, people did voice appreciation for the detectives who busted Western outlaws. Then, in 1874, the agency clashed with the Jesse James gang and found that the public’s allegiances seemed to have shifted. The Pinkertons had pursued the James gang before, to no avail, but that year the Adams Express Company, owners of some property the Jameses had spirited away during a train robbery, contracted Pinkerton to try again. Believing that the James brothers were hiding out at their mother’s farm in January 1875, Pinkerton operatives surrounded the farm and threw an incendiary device inside. The device, S. Paul O’Hara writes in his history Inventing the Pinkertons, “was designed to illuminate the interior of the home,” rather than burn it down or kill the people inside. But the panicked James family threw the menacing-looking shell into the fireplace and it exploded, throwing shrapnel around the room. The projectiles killed the James’ youngest half-brother and amputated their mother’s arm. In the aftermath, public opinion condemned the Pinkertons for their actions.

Why did Americans turn their allegiances from law enforcement to outlaws in this case? The Pinkertons, O’Hara argues, didn’t understand that the James gang had the allegiance of the people of Missouri in part because the Jameses were unrepentant Confederate sympathizers. The James gang refused to respect northern railroads, banks, and government officials, and the order they were trying to impose on the South and West—and that included the Pinkertons. In the raid’s aftermath, Frank Morn writes, “Jesse James became an American Robin Hood, and Pinkerton became the sheriff of Nottingham.”

This historical scene at the James’ farm is reminiscent of a battle between the Pinkertons and the Van der Linde gang in Red Dead 2. In the game, agent Milton surrounds the tumble-down property where the gang is camped out with the women and children who travel with them, and challenges the group to come out and surrender. Milton begins to count down to allow Dutch, the gang leader, a chance to come out, and then stops counting and orders his men to fire at the house, using a serious arsenal that includes a Gatling gun. As Arthur Morgan, the player must figure out how to sneak out of the house and shoot the Pinkertons. (This confrontation particularly disturbed Zahran, who believed it misrepresented the Pinkertons’ methods of pursuit and encouraged players to consider Pinkertons to be targets.)

But it’s not the “bandits-and-railroads” phase of the Pinkertons’ history that most soured the firm’s reputation in the American public eye. Between 1877 and 1892, the Pinkertons were involved in 70 labor union strikes—including some of the biggest and most consequential of the Gilded Age. After Allan Pinkerton’s death in 1884, his sons William and Robert took over, and they doubled down on the project of providing what capitalists and industrialists needed in their struggles with labor. Pinkerton detectives infiltrated labor unions under cover of secrecy, and reported on their activities to employers; Pinkerton guards, acting as visible muscle, protected company property during strikes. The Pinkertons also provided strikebreakers (aka scabs) to fill in for companies when union workers walked out and protected those strikebreakers while they were working.

In a few instances, the Pinkertons killed people while clashing with strikers. The January 1887 shooting of a teenaged bystander, Thomas Hogan, during a coal wharves strike in Jersey City, New Jersey, was a particular catalyst for anti-Pinkerton sentiment. But the tipping point was Homestead. During a strike of the Amalgamated Association of Iron and Steel Workers in 1892, Andrew Carnegie’s plant manager, Henry Clay Frick, hired Pinkertons to protect the company’s steel plant in western Pennsylvania. Three-hundred Pinkerton men rode barges down the Ohio River from Pittsburgh to Homestead in early July. When they arrived on July 6, strikers met them, and shots were fired; a daylong battle ensued, and nine workers and three Pinkerton agents died. O’Hara points out that Pinkerton agents testifying would later say that the first shots came from the crowd, but “popular accounts that quickly followed from the conflict assigned blame to the Pinkertons.”

Pinkerton has provoked passionate disagreements about the relationship between public and private, capitalism and the state.

Regardless of the truth of the conflict’s origin, this period was the nadir in public opinion of the agency. While workingmen loyal to unions had long resented the Pinkertons, conflicts between industrialists and labor also alarmed lawmakers and “respectable” citizens, and they wondered whether the Pinkertons’ existence was making everything worse. In a January 1887 issue of the Nation, after Hogan’s death in Jersey City, the editors described the Pinkertons as “the greatest disgrace that has befallen the United States”—evidence of “our internal weakness and lawlessness,” “an unmistakable sign of retrogression toward medieval barbarism,” with Pinkertons playing the part of a feudal band of mercenaries, earning their keep from barons and lords looking for protection of their property. O’Hara notes several instances in which essayists writing critically about capital’s treatment of labor after Homestead used the word “pinkerton”—lowercase P—to denote “a kind of shorthand for the general violence and tension that marked the struggle over labor and capital in the Gilded Age.” After Homestead, Congress investigated what happened and tried to determine whether the employment of Pinkertons had exacerbated a tense situation.

While a bone of contention between the modern Pinkertons and Take-Two is whether the methods the fictional Pinkertons use to hunt the Van der Linde gang are historically accurate, the mood of opposition between the Pinkertons and gang members in the game is correctly evocative of historical tensions. Red Dead 2’s action occurs near the end of the 19th century, and the Van der Linde gang (Take-Two’s legal documentation alleges) is meant to be analogous to the Butch Cassidy’s Wild Bunch, some of the very last Western bandits, who were chased to Argentina by Pinkertons in 1901. In that first cut scene, Arthur Morgan asks agent Milton: “Do you enjoy being a rich man’s toy?” Milton snarls in response: “I enjoy society, flaws and all! You people venerate savagery and you will die, savagely, all of you!” This late in the 19th century, it’s appropriate that a man like Arthur Morgan, of a countercultural turn of mind, would harbor personal animosity toward the post-Homestead Pinkertons.

In the wake of the poor publicity that came from Homestead and the congressional investigations, the agency turned away from strike-related services and back to chasing criminals. The agency also tried to combat negative publicity with positive—a strategy Allan Pinkerton himself had pioneered, when he wrote (or ghost-wrote) 17 books of popular detective fiction in the 1870s and 1880s. After Homestead, the Pinkertons gave Cleveland Moffett, a journalist from McClure’s magazine, access to their archives, and Moffett wrote a series of stories about the agency—appreciative true-crime tales that had nothing to do with strikebreaking. In the 1890s, O’Hara writes, the agency kept a file of press clippings and “quickly responded to any bad press,” including one piece on the James farm raid that the Pinkertons felt represented them poorly.

The public relations problem continued into the 20th century. In 1914, former Pinkerton detective Charlie Siringo sent his erstwhile employer a manuscript of his book Two Evil Isms: Pinkertonism and Anarchism: by a Cowboy Detective Who Knows, as He Spent Twenty-Two Years in the Inner Circle of Pinkerton’s National Detective Agency. In the book, Siringo called the Pinkertons “a monster agency,” accusing them of organizing mass voter fraud and ginning up false evidence, among other crimes. Siringo published the book privately, the Pinkertons took him to court, and the “printing plates were confiscated and handed over to the Pinkerton agency. … Only a few copies of the book survived,” Frank Morn wrote. (These days, you can buy it on your Kindle for $0.99.) According to Morn, the kerfuffle over Siringo’s book “began a practice, which exists to this day, of controlling publication of works on the agency.”

In the 1960s, as outlaws again came to seem like heroes, Pinkerton agents showed up in Western movies like Butch Cassidy and the Sundance Kid and The Outlaw Josey Wales as (O’Hara writes) “the relentless force of repression and law.” The Pinkertons, who had, in the age of police modernization and beefed-up federal law enforcement, shifted their focus to providing protection services, responded by allowing author James Horan to access their case files and write a book—shades of Cleveland Moffett. Robert Pinkerton II, the great-grandson of Allan and then–head of the agency, provided a preface to the book that described the popular perception of the “Western outlaw” as “an erroneous conception.”

“Is it open season on companies that have achieved longevity? What’s next? A game where Coca-Cola poisons mankind?” — Pinkerton President Jack Zahran

The Pinkertons’ argument with Red Dead 2 seems, from one angle, to be a simple transposition of this company’s long battle to maintain its reputation to a new medium it considers particularly influential. In our conversation, Zahran emphasized the immersive aspect of video games again and again: “It’s a game based on fictitious characters doing fictitious things, reaching a lot of people in a medium that convinces them that it’s real.” He mentioned the results of a poll Esquire embedded in its news post on the Pinkerton/Take-Two conflict. “Have you been moved enough to attempt to murder any Pinkertons after playing ‘Red Dead’?” the poll asks. The poll’s choices—“Several, I’m afraid” and “No, not yet”—make it clear to Extremely Online people, who are used to mocking fears of video game–instigated violence, that this poll may be mostly trolling. But the fact that 41 percent of people chose “Several, I’m afraid” disturbed Zahran. “The fact that this answer isn’t zero is a concern for me, who’s ultimately responsible for life safety for all our employees,” he said.

The Pinkerton website’s historical timeline features a header image that’s a picture of Allan Pinkerton and Abraham Lincoln at Antietam, during the time when Pinkerton served as Lincoln’s personal security—a picture that, O’Hara writes, was “long a key part of Pinkerton lore,” hanging in every office and distributed to prospective clients when it seemed liable to convince them of the company’s probity. Notably absent from the timeline is any mention of strikebreaking, though the entry for the 1890s does mention that the state of Ohio outlawed Pinkertons during this time, fearing they might be hired as a private militia.

“There are going to be spots in any organization that has achieved longevity that you are going to look back with historical perspective and say, you know what, that’s not a moment in our company that we’re proud of,” Zahran replied when I asked him about the Pinkertons’ involvement with union-busting during the Gilded Age. “However, what I would argue, on balance, in a free-market environment where ultimately clients decide whether you live or die, you don’t survive for 167 years if you don’t operate with a high ethical standard.”

These are the questions that the Pinkertons provoke, and they’re questions that are particularly resonant in our new age of inequality. Are enforcers and protectors who serve those who can afford to pay inherently undemocratic? If capitalism, in its evolutions, has paid for the Pinkertons to serve the functions government can’t provide, what does that mean about Pinkertons—and about government? Another entry on the Pinkertons’ timeline touts its service to clients during 21st-century hurricanes, events that create miniature Wild Wests—frontier-like situations, where the government and law enforcement can’t always protect everyone’s property and bodies. Is this fair? In our new Gilded Age, our popular entertainments, like Red Dead 2, are reflecting back our uncertainty and rage about the inequities we’re living through. With a strange twist of history’s knife, once again, the Pinkertons are in the middle.