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Imagine it's February 15th, 1861. You're an undercover Pinkerton agent posing as a stockbroker from Georgia, and you're being escorted into a dark and smoky Baltimore bar. You're here to meet the leader of a secret group of pro-slavery rebels aligned with the newly formed Confederacy. You're investigating rumors that they're plotting to kill the president, Abraham Lincoln. A stone-faced man leads you by the arm through the crowded bar and into a quieter backroom parlor.
Sitting at a scuffed table is the leader of the group, Cipriano Ferrandini, a slight, balding man with an enormous mustache.
After immigrating from Corsica, he opened a barbershop here in Baltimore. He also took up the Confederate cause, and his shop became a gathering place for fellow secessionists. Seeing you approach, he nods for you to sit. Can we get you something? A whiskey, perhaps? Yeah, that'd be nice, thanks. You take a seat as a bartender pours you a drink. Ferrandini stares at you with piercing eyes. So our friend here tells me you're one of us.
"'Nod and raise your glass. "'I think it's admirable what you and your men are doing. "'Yours is a noble cause. "'It's more than noble. "'The future of the country's at stake. "'This is life and death.' "'Well agreed. "'May I ask what you're planning to do about the new president?'
The man who helped set up this meeting has assured you that Ferrandini thinks you're a secessionist and a friend of the South. You know his group is in need of funds, and the $25 donation you made helped get you in the door today. You promised to provide even more financial support, but you can tell he's wary and still sizing you up. Well, you seem like a friend to our cause, so I'll tell you. A week from today, the North will need another president.
Lincoln will be a corpse. What about the authorities? Don't worry about them. They're with us. You'd heard the Baltimore Police Department was full of rebel sympathizers. Now you have some proof, but you need more. How can you be so sure? I've spoken with Police Chief Kane. Let's just say he won't shed a tear over Lincoln's body. But surely Lincoln would be protected while he's here in town. We know he'll have bodyguards, perhaps even Pinkerton agents. But we have a plan.
We're going to cause a little riot in the streets outside Calvert Street Station. And when the police respond to that disturbance, we'll be able to get close enough to Lincoln to take action. And who's going to take this action?
Farandini glares at you. You worry maybe you've asked too much and aroused his suspicion. Oh, I can't tell you any more than that. You understand. Oh, well, of course, of course. Just know this. Lincoln will not leave Baltimore alive. And after next week, all Maryland will be free and the South will soon follow. Farandini stands. And now I'll leave you. But be careful, my friend. There are spies everywhere.
You nod as Ferrandini turns to leave. You've been working undercover on this case for weeks and now finally have proof that the president's life is in danger. You just hope you can get a secret message out fast enough to foil the plot. You and your detective agency are the only thing standing in the way of the murder of the president.
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From Wondery, I'm Lindsey Graham, and this is American History Tellers. Our history, your story. American History Tellers
On our show, we'll take you to the events, the times, and the people that shaped America and Americans. Our values, our struggles, and our dreams. We'll put you in the shoes of everyday people as history was being made. And we'll show you how the events of the times affected them, their families, and affects you now.
The Pinkerton Detective Agency was founded in the 1850s by Scottish immigrant Alan Pinkerton. After working as a detective in Chicago, Pinkerton formed a private crime-fighting agency and recruited elite detectives, including a few groundbreaking women, to chase down counterfeiters, bank robbers, train bandits, and jewel thieves. And in 1861, the growing agency undertook a daring operation to prevent the assassination of President Abraham Lincoln.
Undercover Pinkerton agents obtained crucial information from secret secessionist groups in Baltimore that helped foil the plot.
During the Civil War, Pinkerton and his agents often worked for the Union as undercover spies in Washington and behind Confederate lines. And they would lay the groundwork for the first federal law enforcement organization, the Secret Service. After the war, Pinkerton agents turned their attention to hunting the nation's most notorious Wild West outlaws, from Jesse James to Butch Cassidy and the Sundance Kid.
But by the early 1900s, the agency's aggressive tactics on behalf of powerful corporations led the public to question whose side the Pinkertons were really on.
In this series, we'll trace the origins and evolution of the Pinkerton Detective Agency, from its modest start fighting crime in Chicago to its success as a precursor to modern-day private security firms. And if you want to learn more about how the Pinkertons helped save Abraham Lincoln from a pre-Civil War assassination plot, you can read about it in the forthcoming book inspired by American history tellers. The Hidden History of the White House takes readers inside the iconic seat of American presidential power and
We never sleep.
Alan Pinkerton was born in 1819 into a working-class, crime-ridden neighborhood called the Gorbals of Glasgow, Scotland. The youngest of 11 children, Alan's father died when he was 10 years old. His mother worked at a spinning mill but struggled to put enough food on the table and provide for the large family.
To help make ends meet, Allen left school to work as an errand boy and in a fabric shop. At 18, he became an apprentice barrel maker. He joined the Cooper's Union and became active in a left-leaning political movement called Chartism, named for the People's Charter of 1838, a call for better pay and voting rights for the working class of the United Kingdom. Pinkerton raised funds for the Chartists and joined protest rallies, some of which turned violent.
He later claimed that by 1841, his activities as a labor activist made him an outlaw with a price on his head. A year later, at age 23, he attended a fundraising concert for striking mill workers. There he fell for a pretty young singer named Joan Carfrae. The two married in 1842 and soon left Scotland for America.
But at the end of a stormy four-week journey, their ship ran aground off Nova Scotia. Pinkerton, his wife, and the other passengers were forced to row ashore in life rafts, leaving most of their possessions behind. When they finally did make it to America, the couple decided to head west, first to Detroit, then Chicago, before settling 40 miles further west in Dundee, Illinois, where Alan set up shop making beer kegs.
And it was in 1846 that, while collecting wood for barrel staves on an island on the Fox River, Pinkerton stumbled across the secret hideout of a group of wanted counterfeiters. He notified the local sheriff, then joined the posse that arrested the gang. This led the county sheriff to ask Pinkerton to serve as a part-time deputy sheriff and help with occasional investigations and arrests.
Pinkerton enjoyed the work, so in 1847 he sold his cooperage and he and Joan moved to Chicago. He worked there as a deputy in the Cook County Sheriff's Office before taking a job as a detective for the Chicago Mayor's Office. He quickly made a name for himself as a tough, honest lawman and was then hired as a special agent for the Postal Service where he went undercover and helped break a mail theft ring.
A Chicago newspaper praised his investigative work, declaring, We doubt he has any equal in the country.
These early experiences as an investigator taught Pinkerton some tricks of the trade, but also revealed to him the shortcomings of public law enforcement. He soon saw an opportunity for a private enterprise. In the mid-1800s, as American expansion churned westward, trainloads of goods were being transported across the country. This included safes full of cash and gold, which tempted greedy employees and armed robbers. At the time, publicly funded police departments were still in their infancy.
Small-town cops were untrained, unreliable, and prone to corruption. Both corporations and ordinary citizens often distrusted them, and with no national investigative force to stop these robberies and the murderous gangs behind them, local police were often outmanned and outgunned. Seeing an opportunity, around 1853, Pinkerton created his own private security and investigative force called the Northwestern Police Agency.
Pinkerton's timing was ideal. A number of new courier companies, including American Express and Wells Fargo, were moving goods and currency by rail. And because of the lack of assistance from local law enforcement, these companies began to hire private agencies like Pinkerton's to investigate theft and chase robbers.
So throughout the mid-1850s, Pinkerton expanded his operation, assembling a team of young agents, including former police officers and newspaper reporters. By 1856, Pinkerton had a staff of eight, mostly working on retainer for railroad companies and investigating cases of counterfeiting and fraud. And to protect his agency's reputation, Pinkerton required all his employees to agree to a set of ethical guidelines or guiding principles.
Pinkerton wanted his operatives, as he called them, to be pure and above reproach, men of high order of mind. It wasn't unusual that the field of crime detection was almost exclusively a male profession at the time, and initially Pinkerton's agents were all men. But in 1856, a woman walked into his Chicago office.
Kate Warren, a widower in her 20s, was working as a housemaid when she visited Pinkerton's office and asked for a job. Pinkerton responded by telling her he didn't need a secretary. Warren replied that she was applying to be a detective.
At the time, it was rare for women to work outside the home, let alone in a male-dominated business, and Pinkerton had never heard of a female detective. But Warren convinced him that she could get men to trust her, and unlike a male agent, she'd be able to coax out information from the wives and girlfriends of suspected thieves. She said she could worm out secrets in ways that are impossible for male detectives.
Pinkerton decided to take a chance, and Warren became the first female detective in America, quickly establishing herself as a reliable and effective operative. Pinkerton soon assigned her to a high-profile case involving the theft of $40,000 from the Adams Express Company. It would become his company's first big test.
Imagine it's late May, 1858. You're a female Pinkerton detective working undercover in Jenkintown, Pennsylvania. Your mission is to extract information from a woman whose husband is suspected of stealing from his employer, the Adams Express Company. You had a break in the case a few weeks earlier when the woman's young daughter, Flora, fell while she was running on a gravel path. Luckily, you were nearby and rushed over to help her. The mother, Mrs. Maroney, thanked you and you struck up a friendship.
So today you're walking with Mrs. Moroney and her daughter along the same gravel path through the colorful town gardens. You're hoping today might be the day she divulges some useful information. You decide to play on her sympathies. Oh, well, thank you for walking with me today. I've been in such a melancholy mood that I needed someone to talk to. Well, of course, dear. I enjoy our little walks. Tell me, what's been bothering you? Oh, I worry what you'll think of me. Come now, you can tell me anything. Let's sit down over here.
She steers you to a bench and you both sit while Flora plays with a doll in the grass. Well, the truth is my husband was arrested, charged with forgery. I'm sure he's innocent, but the judge won't let me see him. Without his income, I'm penniless. I don't know what to do.
"'I'm sorry to burden you with this.' "'No, not at all. And since you confided in me, I feel I can do the same. I can understand your situation very well. My husband has also been charged with a crime.' "'He has?' "'Yes, and I'm afraid he's in serious trouble. They've charged him with taking $40,000, stealing it from his employer.'
"'I'm worried Flora might never see him again. "'Well, how can our husbands leave us with no means of taking care of ourselves? "'Well, actually, my husband did recently entrust me with a large amount of money. "'He swears he earned it legally, though, and didn't steal it. "'But I'm not so sure. What are you going to do with it? I don't know.' "'Mrs. Moroney looks around nervously. "'I mean, for now, I've wrapped it in a cloth and buried it in the cellar. "'What do you think I should do?'
You pat her arm and give her a reassuring smile. Nothing. You've been smart. Leave it where it is and wait until your husband instructs you otherwise. That's what I would do. You maintain a doleful expression on your face, but secretly you're thrilled your ruse worked. Mrs. Maroney has confessed her husband gave her the money. You're already eager to send word to your boss that you found the missing cash.
In 1856, the Adams Express Company lost $40,000. They contacted Alan Pinkerton seeking his help to recover it. Pinkerton immediately suspected an inside job and came to believe that Nathan Maroney, an Adams Express Company manager, was the thief.
Maroney had been well-liked and respected by his co-workers. But after he started buying expensive clothes and staying in fancy hotels, Pinkerton had him followed and eventually arrested. But Pinkerton still needed more evidence for a conviction, and his primary objective was to find the missing money. So he assigned Kate Warren to go undercover to befriend Maroney's wife. Warren helped break the case and recovered nearly all the stolen money. Maroney was convicted and sentenced to 10 years in prison.
Pinkerton was impressed by Warren's work and later said, "'She succeeded far beyond my utmost expectations, and I soon found her an invaluable acquisition to my force.'"
Warren was smart and confident, tough yet trustworthy, with an honest face that others opened up to. She was at ease in social settings, but equally comfortable in dangerous situations, delivering classified documents or working undercover. She easily adopted accents and could make herself cry at will. She also became a master of disguise, able to pose as a secretary or an aristocrat.
And after her exemplary work on the Adams Express Company case, Pinkerton rewarded Warren by naming her a superintendent of his new female detective bureau, and he authorized her to recruit more female agents.
The success of the Adams Express job also brought Pinkerton more widespread acclaim. He was soon inundated with new business and decided to rename his company the Pinkerton National Detective Agency. His wife Joan came up with a slogan, We Never Sleep, and Allen created a logo of a wide-open eye to go with it. In time, people would refer to Pinkerton as the Eye, and his agents would become known as Private Eyes.
Pinkerton was now a well-known man of the law, but there was one law he declined to uphold, the Fugitive Slave Act of 1850. This legislation required all officers of the law, public and private, to return runaway slaves to their owners. It also imposed heavy fines on anyone who assisted fugitives.
But Pinkerton had a moral objection to the law. He and his wife Joan, who now had two boys and two girls of their own, were devout abolitionists. Their small cottage in Dundee had served as a safehouse on the Underground Railroad, and Allen had been a representative to Illinois' anti-slavery Liberty Party. He called slavery a curse to the American nation.
And even when the Pinkertons moved to Chicago in 1849, they continued to welcome families fleeing enslavement in the South, providing them with food, clothes, and shelter.
And it was in early 1859 that abolitionist John Brown visited Pinkerton. Brown was helping a group of people escaping slavery make their way to Canada and needed more funding for the journey. Pinkerton not only raised money for Brown's group, but used his connections to secure a special railroad car to carry them the rest of the way from Chicago and into Canada.
because by now, Pinkerton had become acquainted with many of the men who led the railroad companies. One of them was a fellow Scotsman, George McClellan, then an executive with the Illinois Central Railroad. McClellan was a handsome West Point grad and a veteran of the Mexican-American War. After the Illinois Central Railroad hired Pinkerton to investigate a string of robberies, the two men became fast friends. Through McClellan, Pinkerton also met a tall, skinny lawyer who did legal work for the railroad.
Eventually, that lawyer, Abraham Lincoln, was elected president in 1860. And in early 1861, Lincoln made plans for an 11-day railroad tour from his home in Springfield, Illinois, through New England and to Washington, D.C., where he would be inaugurated on March 4th.
Lincoln planned to stop in 70 cities and towns along the way, but despite the contentiousness of his election, Lincoln declined to bring a military escort, and he insisted that his schedule be announced to the public so that crowds could greet him. But then Samuel Felton, president of the Philadelphia, Wilmington, and Baltimore Railroad, heard rumors of a plot to sabotage his rail lines and possibly even harm Lincoln. Felton hired Pinkerton to investigate these rumors.
And after he confirmed that there was an assassination plot, he tried to get Lincoln to cancel the public tour. But the president-elect refused. Pinkerton then came up with a secret plan that he hoped would deliver Lincoln to Washington safely. He assigned his star agent, Kate Warren, to go undercover and play a key role in the mission to keep the president safe. ♪
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The election of Abraham Lincoln in November 1860 brought long-simmering tensions over slavery to a boil. Within a month, South Carolina seceded from the Union, and other southern states soon followed. Lincoln became the target of vicious attacks in the press. Critics and politicians saw him as a threat to their enslaved workforce and their economic power.
But as a lifelong abolitionist, Alan Pinkerton was a strong supporter of Lincoln. So when he discovered that in Baltimore there were threats to Lincoln's safety, Pinkerton sent his best agents and launched an investigation hoping to infiltrate radical organizations rumored to be plotting to kill Lincoln ahead of his inauguration in March. Pinkerton also went undercover himself, posing as a stockbroker from Georgia named John Hutchinson.
In this role, he befriended members of a secret rebel group whose leader, Cipriano Ferrandini, told Pinkerton of their plot to kill Lincoln.
Armed with details about the would-be assassin's scheme, Pinkerton came up with a plan to allow Lincoln to complete his whistle-stop tour, but with extra precautions as he passed through Baltimore. Pinkerton then assigned Kate Warren to pose as a Southern belle named Mrs. Barkley, and on the night of February 23rd, she and Pinkerton traveled by train with Lincoln from Philadelphia into Baltimore. There they had to transfer to another train, and Pinkerton had arranged for Lincoln to be disguised as an elderly invalid where
wearing a large overcoat and a wool cap instead of his trademark top hat. Warren posed as his caretaker and sister, and calling the president brother, she and Pinkerton led Lincoln across a few blocks of downtown Baltimore to the train that would carry him to Washington.
Lincoln traveled the rest of the way in a private room with the shades drawn to prevent anyone from seeing him. And finally, at 6 a.m. on February 24th, Lincoln reached D.C. safely. Pinkerton confirmed the operation's success via telegram, using the codenames assigned to both him and the president, Plums Has Nuts.
Not long after Pinkerton safely shepherded the President to his inauguration, the United States descended into civil war. In April of 1861, Pinkerton wrote to Lincoln, offering his services, stating, I am at your command. Lincoln responded by inviting Pinkerton to come to D.C. to meet with his cabinet. Soon after that meeting, Pinkerton received a letter from his friend in Illinois, the railroad executive George McClellan, who Lincoln had named Commander of the U.S. Army in Ohio.
McClellan asked Pinkerton to join him and create a military intelligence unit in Cincinnati. The goal was for Pinkerton and his agents to gather information on Rebel troop sizes and plans which they'd delivered to McClellan and his generals. Knowing the size and position of Rebel troops was essential to McClellan's military decision-making, and McClellan instructed Pinkerton to travel behind enemy lines and gather intelligence on roads, bridges, and the general feeling of the people residing in the South.
And when McClellan was promoted that summer to lead the larger Army of the Potomac, he named Pinkerton the head of his secret service. Pinkerton's detectives, including Warren and other female operatives, began conducting undercover operations, risking their lives to infiltrate rebel groups and at times traveling deep into Confederate territory.
At one point, Pinkerton posed as a Confederate soldier, calling himself Major E.J. Allen. He traveled alone on horseback, but after being recognized in Memphis, he was forced to flee and barely escaped with his life. Meanwhile, the South had its own spies, and as Pinkerton reported to Lincoln, they were invading the North like locusts. Among the Confederacy's spy ring in Washington, D.C., was a beautiful widowed socialite known as the Wild Rose.
Imagine it's August 23rd, 1861. You're walking up the steps to the front porch of your home in Washington, D.C., two blocks north of the White House. You had hoped to go on a bit of a stroll and deliver a secret message to another spy for the Confederacy. But two men on the street aroused your suspicion, so you abandoned your mission and made your way back to your brick home on K Street. You're about to open the front door when you hear footsteps.
You turn to see the same two men coming up the steps behind you. You recognize one of them, Detective Alan Pinkerton. You decide to confront them. Who are you, and what are you doing here? The man you recognize as Pinkerton speaks up. I'm Major E.J. Allen with Union Army, ma'am. Please step inside.
You know he's lying. By now, half the city knows what Pinkerton looks like, and he works for that Yankee scoundrel, General McClellan. I will not step inside except by myself. You have no business here. Doesn't your government have better things to do than bother defenseless women? We're here to search your house. Now move aside. By whose authority? Pinkerton ignores you.
Nodds to the other man who grabs your arms and pushes you inside. You stumble into the parlor, trying to pull free of the man's grasp. Your mind races. The house is full of evidence of your spying. You try to remember all the places you've hidden letters, messages, and secret codes.
Need to find a way to get into your bedroom alone. Oh, get your hands off me. This is outrageous. You have no right. Madam, we've been watching you, and we know who you've been meeting with. We intend to find the proof we need to lock you away for aiding and abetting the enemies of the Union. Suddenly, the door flings open, and four more men and a woman enter. Pinkerton begins barking orders. All right, check everything. Under the beds and furniture, inside books, picture frames, all of it.
Pinkerton leads you up to your bedroom as the others ransack your home. In your room, you shut the door and rush to your dresser, opening the secret compartment where you've hidden maps, letters, and notes on McClellan's army.
You quickly tear the notes and letters to pieces and throw them into your unlit stove, mixing them with the ashes and hoping they won't be discovered. You strip off your dress and open the door, giving Pinkerton a glimpse of you in your underclothes. You hope it will distract him and he won't discover the shredded secret documents in the stove or any other evidence of your deceit.
In August of 1861, after conducting weeks of surveillance outside the home of Rose O'Neill Greenhow, Alan Pinkerton arrested her on suspicion of spying for the Confederacy. After a raid on her home, Greenhow was held under house arrest and charged with sending vital information about Union troop movements to Southern generals.
In their raid, Pinkerton agents had found plenty of evidence to build a case against her. Secret letters, maps, a small diary, and unburned scraps found in her bedroom stove. All of this proved that Greenhow had been providing intelligence to the Confederacy. So, too, did love letters to Greenhow from Southern sympathizers in Congress. And these findings led to other subsequent arrests of spies and abettors.
Newspapers across the country carried the high-profile arrest of Rose Greenhow and other conspirators, earning Pinkerton more publicity and further bolstering his agency's status. But starting in late 1861, these successes turned to setbacks, including the loss of one of Pinkerton's favorite agents.
Timothy Webster was a British-born spy who had helped Pinkerton uncover the plot on Lincoln's life. Later, in 1861, Webster posed as a Confederate sympathizer and infiltrated the Knights of Liberty, a secret group in Baltimore that was planning an attack on the Capitol. When Webster learned of the plot, he reported it to Pinkerton, who raided the group on Thanksgiving night. Pinkerton even arrested Webster to help maintain Webster's cover.
Later, in 1862, Webster and Hattie Lawton, one of Kate Warren's recruits, were working undercover in Richmond, Virginia, posing as husband and wife. Webster had managed to become a mail courier for the Confederate Secretary of War, Judah Benjamin. He was untrusted with delivering secret messages from Benjamin to Southern sympathizers in Washington. But before delivering these letters, Webster would read them and report his findings to Pinkerton.
But just as this scheme was beginning to bear fruit, Webster fell ill. Pinkerton sent two other agents, Price Lewis and John Scully, to check in on Webster. On February 26, 1862, Lewis and Scully visited Webster at his Richmond hotel. But they were recognized by a Confederate detective and arrested and charged with espionage. In April, Lewis confessed to his captors that he was a Pinkerton agent, which led to charges against Webster, who was sentenced to death.
Webster was hanged by the Confederates on April 28, 1862. Hattie Lawton and the two other Pinkertons were imprisoned for months, but their executions were delayed and they would eventually be released in a prisoner exchange.
Webster's death was a personal blow to Pinkerton, but also a strategic blow to the Union army. Webster had not yet obtained sufficient information on Confederate troops, nor had he managed to recruit Union sympathizers to provide such intelligence. Even worse, some of the preliminary information Webster had been sending Pinkerton turned out to be inaccurate.
One of Webster's reports, sent shortly before his arrest, estimated that there were 116,000 Confederate troops outside Richmond. In fact, there were roughly 75,000. And this meant Pinkerton's friend and head of the Union Army, George McClellan, often had an unclear picture of what his army was up against.
and McClellan's lack of clarity on his enemy's strength often led him to delay military action. McClellan soon developed a reputation for hesitating when he suspected his men were outnumbered, and this indecisiveness created a rift between him and President Lincoln. By early 1862, Lincoln was worried that McClellan was too cautious. Lincoln once said in frustration, If General McClellan does not want to use the army, I would like to borrow it for a time.
So on March 11, 1862, Lincoln removed McClellan as General-in-Chief, but allowed him to remain head of the Army of the Potomac. A week later, McClellan led 120,000 Union troops on a planned assault on the southern capital of Richmond. But at the city of Yorktown, McClellan once again slowed his advance, believing an overwhelming force of Confederate troops were ahead.
Lincoln prodded his general by telegraph to break the enemy line and implored him with an urgent order, you must act. But McClellan again waited. In truth, there were fewer than 10,000 rebel troops at Yorktown, but McClellan's hesitation gave Confederate generals time enough to send reinforcements and meet McClellan's stalled army. McClellan's failure to act at Yorktown and elsewhere stemmed partly from his reliance on estimates of troop size that he had been receiving from Pinkerton spies.
But by summer of 1862, President Lincoln had enough. McClellan's days as the head of the Army of the Potomac were numbered. For Pinkerton, this was a troubling turn of events. The U.S. War Department had become the primary employer of his agents. With McClellan's job in jeopardy, Pinkerton's income and his reputation as the nation's top spy were also on the line. And soon, Pinkerton's loyalty to the president and the Northern cause would face a decisive test.
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On September 22, 1862, Abraham Lincoln issued a preliminary draft of his Emancipation Proclamation. This executive order gave notice to the South that after January 1 of the coming year, millions of African Americans enslaved in Confederate states would be forever free.
Pinkerton had been a vocal and active abolitionist, and he and his wife opened their home to people escaping slavery as a stop on the Underground Railroad. So news of Lincoln's proclamation thrilled him. But his loyalty to his friend McClellan now put him at odds with the president.
McClellan had recently scored a strategic victory at the bloody Battle of Antietam, which ended with Confederate General Robert E. Lee's troops in retreat. But Lincoln had had enough of his overly cautious and impertinent general. In November, Lincoln relieved McClellan of command.
But in support of McClellan, Alan Pinkerton resigned from his Secret Service duties. He and his agents continued to work for the War Department throughout the rest of the war. But Pinkerton returned to Chicago, setting his sights on getting back to what his agency did best, catching thieves. Meanwhile, Pinkerton's departure from military service coincided with a rising star of Lafayette Baker, a Union spy who ran a rival agency, the National Detective Bureau.
In the years to come, both Pinkerton and Baker would take credit for having created the U.S. Secret Service. In reality, it was Lincoln's doing. Shortly after Lee surrendered to Grant at Appomattox, Lincoln approved legislation creating the Secret Service as a federal agency to combat counterfeiters and signed the agency into existence on April 14, 1865.
Later that very night, Lincoln was assassinated. Pinkerton was in New Orleans when he got the news. He immediately wrote to the War Department, expressing his regret that he wasn't able to protect Lincoln as he had in February of 1861. He noted that had he been there with Lincoln, I might have been able to arrest it.
And by 1866, Pinkerton fully put his Civil War service behind him. He called his agents back from Baltimore and Washington and refocused their attention on the West. He also collected Timothy Webster's body from Richmond and had his friend and agent buried in Chicago.
With trains back in business after the war and with the transcontinental railroad connection nearing completion, Pinkerton was soon busier than ever chasing outlaws. And by this time, his sons William and Robert had joined the growing agency. Their new nemesis was a murderous gang of brothers from Indiana who began terrorizing banks, trains, post offices, and other businesses throughout the Midwest.
Imagine it's late evening in early October 1866. You're a courier for the Adams Express Company on board an Ohio and Mississippi Railroad train as it departs Seymour, Indiana.
you're glad to have Seymour behind you. It's a notorious town full of outlaws that a newsman recently called a carnival of crime. The Seymour Times even posted a notice in the paper warning visitors to be wary of thieves and assassins. So it's not a comfortable place for a man like you, one who's responsible for two locked safes full of nearly $50,000 in cash, gold, and bonds.
So as the train picks up speed, you heave a sigh of relief. But just a few miles out of town, someone starts banging on the lock door of your express car, yelling for you to open up. No, no, go away. This is a private car. No passengers allowed. Hey, look, we can come in the easy way or the hard way. Your choice. You realize whoever is banging on the door are not lost passengers. No, don't try. I'm warning you. I'm armed. Yeah, we'll see about that.
Suddenly, the door crashes inward, and you wish you actually had a firearm.
You're facing three masked men, one of whom aims a pistol at your head. Hey, look, we ain't your passengers, son. We're your worst nightmare. Now unlock these safes. What safes? Look, I don't know. The man slaps you across the face. He's clearly angry. Don't waste my time. I know there are two safes on board. Now where are the keys? Here. Here are the keys for the small safe. But I don't have the key for the bigger one. I swear, it's company protocol. Company what? What?
The man slugs you in the face and you drop to the floor. Then he kicks you in the stomach. Come on, boys. We'll take the damn safes with us. Ready? The robbers drag the two safes to the open door and heave them out into the night. One of the men pulls the rope for the emergency belt and the engineer starts to bring the train to a stop. Now you just stay on the ground till we're gone, you hear? Tell your boss to leave you the keys next time. Maybe then you won't get hurt. You stay curled up on the floor as the men escape.
Then you hear the sound of gunfire. They're probably trying to shoot open the big safe, but you know bullets won't do a thing. Maybe they'll leave it behind, happy with the $15,000 from the small safe. Either way, you'll probably get fired once your boss learns you've just been robbed.
In the early years after the Civil War, the Pinkerton Detective Agency found itself in high demand. Post-war crime soared, especially along the railroads that continued to expand westward. Trains carrying passengers, mail, and money throughout remote farmlands at 10 miles an hour made easy targets for gangs on horseback.
The quickly infamous Reno Brothers Gang were the obvious suspects in the Adams Express robbery of 1866 outside Seymour, Indiana. One witness stepped forward to identify two of the Reno Brothers who had been seen on the train. But after that witness was shot and killed, others refused to testify and charges were dropped. The Reno Brothers Gang was considered the nation's first organized band of train robbers.
John, Frank, Bill, and Simi in Reno were petty crooks as teens. But their crimes escalated after the war, when they terrorized towns throughout southern Indiana, robbing banks, merchants, and trains. Alan Pinkerton called them the worst gang of scoundrels in the country. They once threw an Adams Express manager off a moving train, killing the man.
So Pinkerton pledged to stop them, insisting that he was the worst enemy they've got. But it would take years to bring them down, and would nearly cost Pinkerton his own life.
In 1867, one of Pinkerton's agents managed to infiltrate the Reno gang. Using a pseudonym, Dick Winscott posed as a bartender at the Reno's Favorite Saloon in Seymour, Indiana. Winscott gathered enough information for Pinkerton to arrest John Reno, who was convicted of robbery in 1868. Pinkerton's older son, William, then captured a few more gang members in Iowa, but they all escaped from jail. Others of the gang were captured and lynched by vigilante mobs or died in shootouts.
But when Alan Pinkerton learned that the gang's leader, Frank Reno, was holed up in Windsor, Canada, he traveled there to make the arrest himself. He raided Reno's hideout and arrested four gang members. Unable to extradite the men, though, Pinkerton was returning to Detroit when a gunman tried to kill him. Luckily, the man's gun failed to fire, and Pinkerton tackled and held him until police could arrive. Pinkerton speculated that this man was hired by a rival detective agency or possibly the Renos themselves.
But although Pinkerton escaped this episode with his life, his agency was about to experience a great loss. In late 1867, Pinkerton's top agent, Kate Warren, fell sick with tuberculosis. Pinkerton was by her side when she died in her sleep in January of 1868. She was only 35. Pinkerton had her buried in Chicago's Graceland Cemetery beside fellow agent Timothy Webster. He later said, Miss Warren never let me down and called her brilliant, intelligent, and accomplished.
The Philadelphia Press praised her as a fearless, pure, and devoted woman who proved that females are useful in a sphere to which the wants of society have long been loath to assign them. But that was not the only loss Pinkerton was to suffer that year. Only months later, his brother Robert died. Pinkerton wrote in a telegram, The old group is slowly dying off.
Then, in 1869, bad luck came for him when the 50-year-old Pinkerton suffered a debilitating stroke. He managed to recover, walking miles every day and returning to working at his desk, but he would never quite be the same. From that point onward, he walked with a limp and had difficulty speaking.
And even then, tragedy was not done with him. On October 8, 1871, a fire broke out on the west side of Chicago and spread to the Central Business District. Pinkerton's office was destroyed. He was a meticulous record keeper and had amassed thousands of case files. The fire burned them all. The Chicago Tribune summed up the loss by declaring, "...most complete and extensive records of criminal history in America destroyed."
But despite this devastating loss, Pinkerton offered to help Chicago police patrol the streets and prevent looting after the fire. He even posted a notice in the papers declaring that while his agents weren't authorized to arrest potential thieves, they would still shoot to kill. Then, as the city recovered from the fire, Pinkerton began rebuilding his office. He wrote in a letter, "'I will never be beaten. Not all the furies in hell will stop me from rebuilding immediately.'"
By 1872, Pinkerton and his agency had fully recovered and were back to chasing down bank and train robbers. Pinkerton had made his name on such cases, but soon he'd face his most elusive foe yet, the outlaw Jesse James.
From Wander E, this is episode one of our series on the Pinkerton Detective Agency for American History Tellers. In the next episode, Alan Pinkerton's son began to take more control of the agency and expand further. But these new ventures strain the relationship between father and sons, and the agency begins to draw criticism from the public.
If you like American history tellers, you can binge all episodes early and ad-free right now by joining Wondery Plus in the Wondery app or on Apple Podcasts. Prime members can listen ad-free on Amazon Music. And before you go, tell us about yourself by filling out a short survey at wondery.com slash survey. If you'd like to learn more about the Pinkertons, we recommend The Hour of Peril by Daniel Stashower and Liar, Temptress, Soldier, Spy by Karen Abbott.
American History Tellers is hosted, edited, and produced by me, Lindsey Graham, for Airship. Audio editing by Christian Paraga. Sound design by Molly Bach. Music by Lindsey Graham. This episode is written by Neil Thompson. Edited by Doreen Marina. Produced by Alita Rosansky. Our production coordinator is Desi Blaylock. Managing producer, Matt Gant. Senior managing producer, Ryan Moore. Senior producer, Andy Herman. And executive producers are Jenny Lauer-Beckman and Marshall Louis for Wondery.
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