by Eamon Javers
Pinkerton developed a code of ethics for his operatives, to establish the boundaries of the work the company would do, and the clients it would work for. Some of the same ethical dilemmas Pinkerton was attempting to stave off still recur in today’s private intelligence outfits. In his “General Principles,” written in the 1850s, Pinkerton wrote that the role of a detective is “a high and honorable calling.” He laid out some rules to help keep it that way:
The Agency will not represent a defendant in a criminal case except with the knowledge and consent of the prosecutor; they will not shadow jurors or investigate public officials in the performance of their duties, or trade-union members in their lawful union activities; they will not accept employment from one political party against another; they will not report union meetings unless the meetings are open to the public without restriction; they will not work for vice crusaders; they will not accept contingent fees, gratuities or rewards; the Agency will never investigate the morals of a woman unless in connection with another crime, nor will it handle cases of divorce or a scandalous nature.
Pinkerton’s modern-day successors have broken nearly every one of these rules. Pinkerton’s own agency sometimes found the rules hard to follow, especially those regarding unions, and the agency became a combatant in the epic battles between labor and capital during the late nineteenth century. Despite their pro-union rules, the Pinkertons would come to be seen as the enemies of the labor movement in the United States.
OVER TIME, ALLAN Pinkerton became an expert in every type of crime that afflicted his corporate and individual clients. His book Thirty Years a Detective (1884)* is divided into chapters detailing the criminals he saw, including “the society thief,” “hotel thieves,” “steamboat operators,” “confidence and blackmail,” and something he called “the Boodle Game,” in which con men sent anonymous letters enticing their targets to engage in financial shenanigans.† The boodle game seems to have been a forerunner of the Nigerian e-mail scams of today. People who’d been suckered into losing money on the schemes were often so embarrassed that they didn’t report the crime to the police.
The Pinkerton Agency battled corporate thieves, stalked bank robbers, and chased Butch Cassidy and the Sundance Kid and the Jesse James gang across the Wild West. During the Civil War, Pinkerton agents foiled an early attempt to assassinate President Lincoln and sent spies into the Confederacy to monitor its military strength and political developments. One of Pinkerton’s agents, Timothy Webster, was hanged in Richmond in 1862 as a Union spy. He was the first American executed for espionage in nearly 100 years.
Pinkerton was already at the height of his powers in the 1850s when he sent undercover agents to nail Nathan Maroney, manager of the Montgomery, Alabama, office of the Adams Express Company, which transported goods by railcar. In 1855, Pinkerton received a strange letter from Edward Sanford, an executive at Adams. Sanford told Pinkerton that $40,000 had been stolen from a company pouch somewhere between Montgomery, Alabama, and Augusta, Georgia. Sanford’s letter included key details of the company’s own internal investigation, including that the leather bag containing the money had been locked when the cash went missing. With nothing to go on but the details contained in the letter, Pinkerton made an educated guess that the thief was Maroney, who would have had access to Adams’s pouch keys. He mailed back his hunch.
Sanford summoned Pinkerton to Alabama and told the detective that he’d already had Maroney arrested and charged with theft. But the company had nothing other than circumstantial evidence against him, and the arrest caused an uproar among the leading citizens of Montgomery, who supported Maroney. After all, Adams Express was a Yankee company and this was the eve of the Civil War. Maroney was a local man, and he had local support. He got out on bail. The situation was verging on disaster for Adams Express.
Pinkerton brought in a five-person team, including Kate Warne, who is widely credited with being the nation’s first woman detective.* The group suspected that Maroney had stashed the money in a safe place until the heat blew over. They needed to figure out where the money was and prove that Maroney had stolen it. They tailed Maroney’s wife as she dropped off a letter to Philadelphia, which tipped them off that she had relatives in that area. When she relocated to the outskirts of Philadelphia, Pinkerton dispatched agents to Jenkintown, Pennsylvania. One operative set up a watch-repair shop in the village as a cover operation and began gathering information on the Maroney family’s activities.
Pinkerton sent in Kate Warne, posing as a society wife. Supplied with a lavish wardrobe, she played her part to the hilt, and wangled an introduction to Mrs. Maroney. Over the course of their chats, Warne pretended to confide in her, claiming that her own husband had gotten rich as a counterfeiter.
Meanwhile, Pinkerton maneuvered to have authorities rearrest Maroney, and when they did, Pinkerton placed an operative, John White, undercover in the same jail cell, ostensibly charged with forgery. Pinkerton then unleashed an elaborate scheme of psychological warfare against the hapless, imprisoned Maroney. An undercover agent was assigned to court Mrs. Maroney in Jenkintown, and to make sure he was seen with her in public. Pinkerton began to barrage Maroney, still in jail in Alabama, with anonymous letters claiming that his wife was having an affair. On her next visit to the prison, Mrs. Maroney admitted she’d been out with the stranger, confirming Maroney’s darkest suspicions.
Sitting right there in the jail cell was Pinkerton’s operative John White, ready to serve as a shoulder for Maroney to cry on over his wife’s supposed infidelity. White hinted to Maroney that it was possible to bribe the authorities to get out of jail early, and when White’s “lawyer”—another of Pinkerton’s actors—showed up to release him, Maroney took the bait. He begged White to help him get out, too, no matter how much it cost. Maroney was desperate to reach his wife. White agreed to help once he’d gotten out of jail, and he encouraged Maroney to get word to his wife that he’d need the stolen cash for bribe money. Maroney sent a message to his wife to dig up the money from its hiding place and give it to White, who Maroney thought would bring it to Alabama and help arrange his release from prison.
When she got the message, Mrs. Maroney wasn’t sure that the scheme was a good idea. After all, Maroney was under suspicion of theft, and getting caught with the cash might seal his fate. But Pinkerton had foreseen that Mrs. Maroney might balk, and had a plan to encourage her along. The anxious woman turned to her new best friend and asked what to do. Kate Warne advised her that paying the money was the best plan. The couple could head out west with their booty, and escape the Alabama authorities.
When Mrs. Maroney handed the money over to White, only $400 of the total amount stolen was missing.
In late 1855, Maroney went on trial in Montgomery, White never having returned to release him. He was shocked to see White called to the stand to testify against him. Realizing he’d been set up and the state had all the evidence it needed to convict him, Maroney pleaded guilty, and was sentenced to ten years in prison. Adams Express put the Pinkertons on an annual retainer, and the Maroney case led to a wealth of new business for Pinkerton.
AS THE NATION collapsed into the Civil War, the Pinkerton Agency was the premier intelligence operation in the country. It had a nationwide force in place, and had developed unparalleled investigative techniques. An avowed abolitionist who worked to spirit escaped slaves to Canada, Pinkerton even helped raise money for the militant antislavery agitator John Brown’s escape from lawmen. When hostilities broke out in 1861, Pinkerton was well positioned and motivated to serve the Union. He knew President Lincoln—who, as a lawyer and budding politician, had drawn up Pinkerton’s contract with the Illinois Central railroad in 1855—and he was close to an energetic young railroad executive named George McClellan.
When McClellan reentered military service (he had once been at West Point) to lead the Ohio state volunteers, he summoned Pinkerton to his side as the head of a military “secret service.” In those days, there was no
separate intelligence service, and individual military leaders gathered battlefield and political intelligence on their own. Using the nom de guerre “E. J. Allen,” since by then “Pinkerton” had become almost synonymous in the public imagination with detective work, the great investigator entered military service.
There’s no question that Pinkerton was an American patriot and a true believer in the Union cause. He’d put his career and life on the line more than once to help slaves escape to freedom. But much like his contemporary successors, Pinkerton was a private intelligence contractor who found war a profitable business. In his comprehensive history The Eye That Never Sleeps (1982), Frank Morn notes that Pinkerton earned what was then a princely sum of $38,567 for his government work between September 1861 and November 1862. After the war, he wrote in a letter to his son that he had been relatively poor before combat began, but that during the war, he “amassed considerable money, which was all invested in property of one kind or another in Chicago.”
To this day, selling private intelligence services to the government in wartime can be a profitable enterprise. An entire industry has evolved around it, and many of these enterprises have headquarters outside Washington, D.C., where the other “Beltway bandits” set up shop selling services to the feds. Among the intelligence contractors of today are well-known names such as Booz Allen Hamilton, with 19,000 employees and more than $4 billion in annual revenue, which depends on consulting work for the U.S. intelligence community. At the other end of the scale is the relatively small corporation Abraxas, which, the Los Angeles Times revealed in 2006, creates fake identities and dummy companies for undercover CIA employees around the world. Some of today’s intelligence contractors have gotten into trouble. The CEO of an obscure contractor, MZM, was found in 2005 to have paid more than $1 million in illegal bribes to a powerful congressman in exchange for classified contracts. And the role of the security contractor Blackwater drew attention during congressional hearings in 2007 on the conduct of the firm’s employees in Iraq, who had been accused of murdering innocent civilians.
But first there was Pinkerton.
AFTER LINCOLN WAS elected president of the United States in November 1860, planning began for his triumphal journey from Illinois to the capital. Cities all along the rail route offered the president-elect the chance to speak to large, adoring crowds. But the route was scheduled to go south from Philadelphia to Baltimore, Maryland—an area with thousands of people, known as copperheads, who sympathized with the South. At that moment, it wasn’t clear whether Maryland would end up in the Union or as a Confederate state. Debate raged in the state capital at Annapolis. Lincoln would have to traverse this dicey geography on his way farther south to Washington, D.C. Samuel Morse Felton, the president of the Pennsylvania Central Railroad, was in charge of organizing the logistics of the trip, including arranging for special presidential trains and setting schedules. He called on Allan Pinkerton, saying he’d heard that Maryland’s secessionists were planning violent reprisals if the state voted to stay in the Union.
Pinkerton put together a plan to protect the president-elect. James Mackay has laid out the detailed preparations in his book Allan Pinkerton: The First Private Eye. The Pennsylvania Railroad organized rail workers and drilled them as a kind of a railway militia. Concerned that copperheads would try to burn train bridges, the workers covered the bridges with coats of fresh paint and fireproof materials. Felton sent men to infiltrate the Maryland militia, to figure out which units might stay loyal and which tilted toward the Confederacy.
Meanwhile, Pinkerton sent in a top team of detectives, including Timothy Webster, Hattie Lawton, and Pinkerton’s own assistant, Harry Davies. Pinkerton trawled the bars of Baltimore using an undercover alias—“J. H. Hutcheson” of Charleston, South Carolina—looking to identify copperheads and their supporters. At the same time, Davies befriended one transplanted southerner during nights of carousing at Anne Travise’s house of prostitution in Baltimore. The man bragged to Davies that he was plotting with a recent immigrant to assassinate President-Elect Lincoln as his train rolled through town. Webster enlisted undercover in the Confederate militia, and heard that it, too, was planning an assassination.
This was enough to convince the team that Lincoln would be in real danger as he passed through Baltimore. Eventually, Pinkerton and his team ferreted out the details of the plot—a small band of men would strike at the Calvert Street train depot. Lincoln heard similar rumors of a plot against him from law enforcement agents as well, and weighed whether to travel to Baltimore as planned or skip the city on his way from Harrisburg, Pennsylvania, to Washington, D.C. As Lincoln’s train left Harrisburg, the American Telegraph Company cut all the telegraph lines running out of the city. That shut down communication into and out of Harrisburg, but it also prevented any southern spies from alerting colleagues in Philadelphia and Baltimore that the president-elect was on the move.
Pinkerton knew that the presidential train would be an irresistible target. He decided to bring Lincoln to Washington ahead of schedule on a regular passenger train, instead, and roll the presidential train though on its regular timing as a decoy. Incredibly, he left Mary Todd Lincoln and her sons aboard the decoy train. Perhaps that was to lend a sense of realism to the procession, or maybe this was simply an era in which no one could contemplate that the assassins might strike at a woman and children.
The undercover Pinkerton agent Kate Warne rented the two rear sleeping cabins of the regular southbound passenger train out of West Philadelphia, telling ticket agents that she needed to transport her brother, who she claimed was an invalid. Felton and a small squad of Pinkertons spirited Lincoln into the cabin. Allan Pinkerton stood by Lincoln’s door, and handed the tickets to the train conductor, never revealing who was in the cabin with him.
Pinkerton deployed agents along the train’s route, to watch for saboteurs trying to blow up the tracks or assassins preparing to assault the train. They waited in preset positions with lanterns to signal the train that all was well in each sector. Allan Pinkerton stood on the rear platform monitoring progress, sector by sector. The train left Philadelphia late in the evening, and pulled into Baltimore at 3:30 A.M., where it paused at the platform. This stop was the moment of highest danger. Only a few armed Pinkertons stood between the roiling population of Baltimore and a vulnerable Abraham Lincoln.
All they heard, though, was a drunk on the platform singing “Dixie” at the top of his voice. After an agonizingly long wait at the Baltimore station, the train rolled on to Washington, arriving at 6 A.M.
Later, when the decoy presidential train rolled into Baltimore, a menacing crowd of thousands gave lusty cheers for Jefferson Davis and the Confederacy. But all they could do was holler.*
THE PINKERTONS STAYED in government service throughout the Civil War, and the company continued to operate its corporate service out of its Chicago offices. The Pinkerton precedent of intertwining private-sector intelligence agencies with government service continues to this day.
Allan Pinkerton went to work for General George McClellan’s army of Ohio, taking the rank of major. He turned to Timothy Webster, one of his most trusted agents, to help infiltrate the Confederacy. An Englishman who’d begun working for Pinkerton in 1853, Webster was dressed in the classy outfits of a dapper Brit, posing as a rebel-loving copperhead. At this point, the British were teetering toward full diplomatic recognition of the Confederate government, which would have been a blow to Union hopes for reconciliation.
Webster set up shop in Baltimore and cultivated copperhead contacts. He soon met the members of a secret society of Confederate loyalists called the Sons of Liberty, and heard from them about plans to stir up trouble for the federal government in Maryland. Thanks to Webster’s spying, Pinkerton agents pinned down the date of a large copperhead gathering. Webster himself, still undercover, was one of the keynote speakers, haranguing the audience with anti-Union rhetoric. But just as he reached fever pitch, Allan Pinkerton, a squad of de
tectives, and dozens of federal troops burst into the room and arrested the leaders of the plot.
Later, Webster made his way south, and reached out to the Confederate government, brazenly offering his services as a spy against the North. The Confederates employed him, giving him access to high echelons of their government and all kinds of Confederate facilities.
Now working as a double agent, he compiled detailed reports on the military installations he saw, including fortifications in the strategically significant town of Yorktown, Virginia, which sits at the southern end of Chesapeake Bay and might have offered invading waterborne Union troops quick access to the Confederate capital, Richmond. The fortifications, he wrote, were “of split-pine logs with a 64-pounder [cannon] with a traverse of 180 degrees,” and the town’s landing was “in front of a hill with a slope of five feet above the beach.” He also included the price points for various goods in the town, giving the Union military leaders a sense of the troubled economy there.
Despite this detailed and accurate reporting—which he risked his life to deliver—many historians have highlighted Webster’s one great failure, which was also the signal failure of the Pinkerton agency during the war. Webster guessed in his reports that the Confederate troops near Richmond numbered 116,430. But it appears that his estimate was too high by far—there were actually 40,000 fewer troops in the area. That miscalculation may have contributed to General McClellan’s reluctance to attack the southern force. That in turn led to intense political antagonism between McClellan and Lincoln, who was pressing for an onslaught against the Confederate positions.
