Before they were the grumpy guys chasing your gang in Red Dead Redemption 2, the Pinkerton Detective Agency was the most famous name in private law enforcement in the United States. Founded by Scottish immigrant Allan Pinkerton in the mid-1800s, the agency guarded presidents, infiltrated secret societies, chased Wild West outlaws, and crashed headfirst into the rise of organized labor.
Some of their exploits are heroic, some are brutal, and quite a few are downright controversial. But “legendary”? Oh yes. Let’s walk through 10 of the most famous (and infamous) episodes in Pinkerton historyand then look at what it all feels like from a modern perspective.
1. Smuggling Abraham Lincoln Through the Night
The Baltimore Plot
In early 1861, president-elect Abraham Lincoln boarded a whistle-stop train tour to Washington, D.C. The country was coming apart, Southern states were seceding, and rumor mills were buzzing with assassination talk. Allan Pinkerton was hired by the Philadelphia, Wilmington & Baltimore Railroad to quietly check out one particularly scary threat: a plot to kill Lincoln when his train passed through Baltimore.
Pinkerton’s agentsmost famously Kate Warne, often cited as the first female professional detective in the United Stateswent undercover in Baltimore’s secessionist circles. They reported a plan to attack Lincoln during a crowded public transfer between stations. Rather than cancel the trip and tip off the conspirators, Pinkerton proposed a more theatrical solution: change Lincoln’s schedule, disguise him, and rush him through Baltimore ahead of time in the dead of night.
Lincoln agreed, reluctantly. With telegraph lines cut to slow the spread of news, Warne and Pinkerton hustled him onto a night train, dressed him down in a soft cap and shawl, and quietly moved him through the city while most of Baltimore slept. The next day crowds still showed up expecting a public appearanceand found only empty tracks. Whether the conspiracy would actually have succeeded is still debated, but the daring midnight ride cemented the legend of Pinkerton’s motto: “We Never Sleep.”
2. Running a Secret Spy Ring for the Union Army
America’s Early Military Intelligence Service
After Lincoln took office and the Civil War erupted, Pinkerton didn’t just go back to chasing counterfeiters. He built one of the first organized military intelligence services in U.S. history. Working for General George B. McClellan and the Army of the Potomac, Pinkerton created a network of scouts and spies across the Confederacy.
His agents slipped behind enemy lines disguised as Southern soldiers, sympathizers, and traders, gathering information about troop movements and defenses. Pinkerton himself went undercover using the alias “Major E. J. Allen.” Reports flowed back to Union headquarters in a steady stream of interviews, observations, and intercepted gossip.
Here’s the twist: modern historians generally agree that Pinkerton’s estimates of Confederate strength were wildly high. McClellan trusted those numbers, became convinced he was badly outnumbered, and often hesitated to attack. So this “legendary exploit” is a mixed bag. On one hand, the Pinkertons helped invent a more organized style of military intelligence. On the other, their flawed numbers fed one of the Union’s most cautious generals. It’s a reminder that “legendary” doesn’t always mean “flawless.”
3. Hunting the First Big Train Robbers: The Reno Gang
When Crime Moved Onto the Rails
In October 1866, the Reno Gang in Indiana pulled off something entirely new: a robbery on a moving train. They boarded an Ohio & Mississippi Railway train near Seymour, overpowered the express messenger, cracked one safe, and shoved a heavier one off the side for accomplices waiting along the line. Overnight, they proved that trains weren’t just transportationthey were mobile bank vaults.
The stolen money was insured by the Adams Express Company, which promptly called in the Pinkertons. Allan Pinkerton and his son William led the investigation, tracking the gang through a trail of botched alibis, nervous witnesses, and brash follow-up robberies.
Over time, Pinkerton agents identified Reno members, shadowed them across state lines, and brought several to justice. Some were arrested and imprisoned; others met vigilante “justice” when local citizens decided that ropes were faster than courts. The Reno pursuit made national headlines and showed that if railroads were the arteries of the new America, Pinkerton detectives were going to be the immune systemsometimes overzealous, but undeniably aggressive.
4. The Bloody War with Jesse James
When the “Private Eye” Met the Outlaw Myth
By the 1870s, railroad robberies were practically a genre, and Jesse James was its breakout star. After the James gang hit an Adams Express car at Gads Hill, Missouri, the company once again turned to Pinkerton. Allan Pinkerton took the case personally, seeing the gang as both a professional insult and a threat to law and order.
Pinkerton agents followed leads, planted informants, and tried to penetrate the gang’s tight circle of relatives and ex-Confederate sympathizers. The feud escalated in 1875, when a team of Pinkertons launched a nighttime raid on the James family farm in Kearney, Missouri. An explosive device thrown into the house killed Jesse’s young half-brother and severely injured his mother, Zerelda.
The raid horrified much of the public. Instead of seeing the Pinkertons as heroic crime-fighters, many people now saw them as ruthless mercenaries willing to blow up a house to get their man. The railroads eventually stopped funding the hunt, and Allan Pinkerton abandoned the pursuit. Legally, the mission was a failure. But in terms of legend, it was hugecementing the James–Pinkerton feud as one of the most dramatic clashes in Wild West lore.
5. Going Undercover with the Molly Maguires
James McParland’s Long Game
In the coal towns of 1870s Pennsylvania, explosions, shootings, and ominous warning notes became terrifyingly common. A secretive group known as the Molly MaguiresIrish immigrant miners accused of mixing labor activism with violent intimidationwas blamed. Mine operators and railroad executives hired the Pinkerton Agency to break the alleged conspiracy.
Allan Pinkerton dispatched James McParland, an Irishman himself, to infiltrate the group under the alias James McKenna. For years, McParland worked in the mines, drank in the saloons, and carefully built trust among suspected Mollies while secretly sending reports back to his Pinkerton handlers.
Eventually, his testimony became the star attraction in a series of dramatic trials. Around twenty alleged Molly Maguires were convicted and hanged. Supporters still argue the trials were stacked and that the “Mollies” were convenient scapegoats for unions at a time when big business wanted to crush worker organizing. Critics, in turn, point to the very real violence that preceded the crackdowns. Either way, McParland’s undercover operation remains one of the most controversialand technically impressivecases in detective history.
6. The Homestead Steel Showdown
Pinkertons vs. Labor on the Monongahela
Not all Pinkerton “exploits” look heroic in hindsight. In 1892, workers at Andrew Carnegie’s Homestead Steel Works near Pittsburgh went on strike to resist wage cuts and union-busting tactics. Plant manager Henry Clay Frick decided to lock out the union and hired around 300 armed Pinkerton agents to secure the mill and protect incoming strikebreakers.
Under cover of darkness, the Pinkertons attempted to reach the mill by river barge. Thousands of armed workers and local supporters were waiting on the riverbank. A violent gun battle followed; deaths and injuries mounted on both sides, and the Pinkertons eventually surrendered and were marched through an angry gauntlet of townspeople.
The Homestead confrontation was a public relations disaster for the agency. Images of corporate “hired guns” firing on workers fueled national outrage and led to the federal Anti-Pinkerton Act of 1893, which barred the U.S. government from hiring the agency. Still, the episode is undeniably legendary: it reshaped labor history, corporate security, and the Pinkerton brand all at once.
7. Chasing the Wild Bunch and the Great Train Robbers
From the West’s Open Range to Malta, Montana
The Pinkertons didn’t ride off into the sunset after the James gang. As train robbery became the outlaw profession of choice, the agency’s detectives repeatedly crossed paths with the Wild Bunch, including Butch Cassidy and the Sundance Kid.
After the famous Wilcox train robbery in Wyoming, Pinkerton men were quickly in the field, following spoor and interviewing witnesses. Later, when members of the Wild Bunch such as Kid Curry hit a Great Northern train near Malta, Montana, and escaped with tens of thousands of dollars, railroad and express companies once again leaned on Pinkerton experience.
The detectives didn’t always get clean courtroom victoriessome outlaws fled, some disappeared, some died in shootoutsbut the relentless pursuit contributed to the end of the romantic “open frontier” era. Train companies beefed up security, and the mere hint that Pinkertons were on the case was enough to panic some would-be bandits into early retirement.
8. The Steunenberg Assassination and the Big Labor Trial
McParland Returns
In 1905, former Idaho governor Frank Steunenberg was killed by a bomb rigged to his front gate. Suspicion quickly fell on radical elements within the Western Federation of Miners, which had clashed with mine owners and state authorities in earlier violent labor disputes.
Once again, James McParland of Molly Maguire fame took center stage as a Pinkerton agent. A suspect named Harry Orchard was arrested and, under intense pressure, confessed to the bombing and implicated top union leaders, including WFM president “Big Bill” Haywood.
The resulting trial was front-page news. Orchard, guided by McParland, testified against Haywood and others. The defense, led by famed lawyer Clarence Darrow, poked holes in his story and painted Orchard as an unreliable self-confessed assassin trying to save his own neck. In the end, Haywood was acquitted, but Orchard received a commuted death sentence and spent the rest of his life in prison.
The case showcased both Pinkerton skill in building sprawling conspiracy investigations and the deep distrust many Americans had developed toward private detective agencies used to police labor conflicts.
9. Cracking the Big Express Safe Robbery
Early Forensics and Follow-the-Money Work
Not every famous Pinkerton case involves gun smoke and train rooftops. In 1866, thieves stole an enormous sumhundreds of thousands of dollars in bonds and cashfrom a train safe. The robbery rattled banks and insurance companies that had built their business models around the supposed safety of express shipments.
Pinkerton detectives stepped in with a methodical, almost forensic approach that felt unusually modern at the time. They studied safe-cracking techniques, examined the crime scene, and tracked suspicious financial movements and sudden spending sprees. Instead of relying solely on confessions, they built a case based on patterns of behavior, timing, and access to the cars and vaults.
The thieves were eventually identified and arrested, and much of the stolen value was recovered. Newspapers played up the story of brainy detectives who used patience rather than pistols, helping to brand the agency as something more than muscle for hire.
10. Building America’s First Private Crime Database
“We Never Sleep” Meets Paperwork
Behind the headline-grabbing exploits, the Pinkertons quietly built an enormous archive of criminal intelligence. They collected mugshots, physical descriptions, handwriting samples, modus operandi notes, and correspondence on outlaws ranging from train robbers to counterfeiters.
Over time, this trove became one of the most comprehensive private criminal records systems in the world. Long after the Old West era ended, the agency’s files on figures like Jesse James, Butch Cassidy, and the Reno Gang were donated to the Library of Congress and other repositories, where historians still study them today.
In an era before a national police force or FBI, this private card-catalog of crime helped railroads, banks, and law enforcement agencies recognize repeat offenders and connect crimes across state lines. It’s not as cinematic as Pinkerton agents shooting it out on river barges, but it may be the agency’s most influential exploitthe groundwork for modern criminal intelligence and record-keeping.
What These Pinkerton Tales Feel Like Up Close
Myth, Morality, and a Whole Lot of Gray
Step back from the gunfights and train whistles for a moment, and the Pinkerton story gets much more complicatedand more interesting. If you binge their history as if it were a long-running crime drama, you’ll notice the show keeps changing genres.
Early on, you’re basically watching a superhero origin story. Pinkerton sniffing out counterfeiters in the woods, racing the clock to protect Lincoln, building a spy network for the Union Armythese are classic “lone genius versus chaos” episodes. The agency looks like a scrappy force for order in a country that’s literally coming apart at the seams.
Then the series shifts. Once the railroads and industrial giants start writing the checks, the Pinkertons become something closer to a corporate security army. The same skills that made them brilliant at undercover work and surveillance now get aimed at labor unions and radical organizers. The Homestead Strike sequence feels less like “detective adventure” and more like a cautionary tale about what happens when private force collides with democratic rights.
If you dig into the details of cases like the Molly Maguires or the Steunenberg assassination, you also start to see how fragile “truth” can look when it’s being filtered through undercover reports, pressured confessions, and trials soaked in politics. Were Pinkerton agents exposing murderous conspiracies? Inflating threats for their clients? A bit of both? Reasonable people still argue about it.
From a modern perspective, the most relatable part of the Pinkerton legacy may be the tension it highlights: Who gets to control information and force? Governments? Corporations? Private contractors? When tech companies hire private intelligence firms to investigate cyberattacks or employee leaks today, they’re walking a path Allan Pinkerton helped clearwith all the same questions about oversight, accountability, and bias.
If you’re a history nerd, reading Pinkerton’s own memoirs and then comparing them with court records and newspaper accounts is a strangely fun exercise. The official agency story often leans heroic; other sources remind you there were scared workers, grieving families, and sometimes very messy facts in the background. It’s like comparing a glossy true-crime podcast with the unedited police files.
And if you’ve only ever met the Pinkertons as the relentlessly annoying pursuers in movies, TV shows, or video games, the real history adds depth. Yes, they really did chase train robbers and outlaws across the West. Yes, they really did serve as early intelligence officers and presidential bodyguards. But they also helped shape labor policy, fueled debates about private policing, and left behind an archive that still feeds historians, novelists, and game developers.
In other words, the Pinkerton Detective Agency wasn’t just a gang of stoic men in bowler hats. It was a powerful, evolving machine operating at the intersection of law, money, and politics. Its “legendary exploits” are excitingbut understanding who hired them, who feared them, and who fought them is where the real story lives.
