Lincoln's Spies: Their Secret War to Save a Nation

Lincoln's Spies: Their Secret War to Save a Nation

by Douglas Waller
Lincoln's Spies: Their Secret War to Save a Nation

Lincoln's Spies: Their Secret War to Save a Nation

by Douglas Waller


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A major addition to the history of the Civil War, Lincoln’s Spies is a riveting account of the secret battles waged by Union agents to save a nation. Filled with espionage, sabotage, and intrigue, it is also a striking portrait of a shrewd president who valued what his operatives uncovered.

Veteran journalist Douglas Waller, who has written ground-breaking intelligence histories, turns his sights on the shadow war of four secret agents for the North—three men and one woman. From the tense days before Abraham Lincoln’s inauguration in 1861 to the surrender at Appomattox four years later, Waller delivers a fast-paced narrative of the heroes—and scoundrels—who informed Lincoln’s generals on the enemy positions for crucial battles and busted up clandestine Rebel networks.

Famed detective Allan Pinkerton mounted a successful covert operation to slip Lincoln through Baltimore before his inauguration to foil an assassination attempt. But he failed as General George McClellan’s spymaster, delivering faulty intelligence reports that overestimated Confederate strength.

George Sharpe, an erudite New York lawyer, succeeded Pinkerton as spymaster for the Union’s Army of the Potomac. Recruiting skilled operatives, some of whom dressed in Rebel uniforms, Sharpe ran highly successful intelligence operations that outpaced anything the enemy could field.

Elizabeth Van Lew, a Virginia heiress who hated slavery and disapproved of secession, was one of Sharpe’s most successful agents. She ran a Union spy ring in Richmond out of her mansion, with dozens of agents feeding her military and political secrets she funneled to General Ulysses S. Grant as his army closed in on the Confederate capital. Van Lew became one of the unsung heroes of the war.

Lafayette Baker was a handsome Union officer with a controversial past, whose agents clashed with Pinkerton’s operatives. The unscrupulous Baker assembled a retinue of disreputable spies, thieves, and prostitutes to root out traitors in Washington, D.C. But he failed at his most important mission: uncovering the threat to Lincoln from John Wilkes Booth and his gang.

Behind these secret operatives was a president, one of our greatest, who was an avid consumer of intelligence and a ruthless aficionado of clandestine warfare, willing to take chances to win the war. Lincoln’s Spies, as Waller vividly depicts in his excellent new book, set the template for the dark arts the CIA would practice in the future.

Product Details

ISBN-13: 9781501126840
Publisher: Simon & Schuster
Publication date: 08/06/2019
Pages: 624
Sales rank: 861,131
Product dimensions: 6.20(w) x 9.10(h) x 1.80(d)

About the Author

Douglas Waller is a former correspondent for Newsweek and Time, where he covered the CIA, Pentagon, State Department, White House, and Congress. He is the author of the bestsellers Wild Bill Donovan, Big Red, and The Commandos, as well as critically acclaimed works such as Disciples, the story of four CIA directors who fought for Donovan in World War II, and A Question of Loyalty, a biography of General Billy Mitchell. He lives in Raleigh, North Carolina.

Read an Excerpt

Lincoln’s Spies
Though they were still traveling through territory infested with secession sympathizers, the ride from Baltimore to Washington early the morning of February 23, 1861, proved uneventful. Allan Pinkerton finally relaxed. He joined Ward Hill Lamon in sipping from a liquor bottle. Pinkerton had not been particularly thrilled with Abraham Lincoln’s hard-drinking Illinois law crony tagging along—the fewer people involved in this operation the better, he believed—but Mary Lincoln had insisted that the burly bodyguard accompany them as the detective escorted her husband on the dangerous trip to the nation’s capital. The blustery Lamon, who sported a uniform he designed for himself, brought along two pistols, a large bowie knife, a pair of brass knuckles, and a thick hickory stick. Though Pinkerton usually abstained from alcohol (he told his son it made him grumpy), the detective could become a cigar-smoking whisky drinker if he needed to play one working a case.

Friends and associates believed Allan Pinkerton was gifted with courage and unusual powers of observation. As a young man he had been a labor agitator, falling under the spell of Scottish revolutionaries. He now hated slavery and had become a fanatical abolitionist. He thought his parents had been atheists and he considered himself one as well. He had honed a sixth sense to anticipate criminal activity before it happened. He was stubbornly persistent, refusing to be worn down by adversity. Yet he could be a tiresome prig, who harangued employees, friends, and relatives about the virtues of honesty, integrity, and courage. He was a tyrant at home, completely dominating his wife and children. He had dark, brooding eyes set deeply under a wide brow with a heavy beard that covered his face, save for his upper lip that he occasionally shaved. He was usually dour and humorless, only occasionally showing a sense of humor. He was a master publicist, skilled at promoting his business and shameless about air brushing his image. He was a disciple of phrenology, the pseudo-medicine that determines a person’s character and intellect from measurements of the head’s size and shape. A phrenologist examined him, writing that the detective’s brain measured twenty-three inches (“very large,” the professor reported) and concluding that he was blessed with “earnestness, enthusiasm, heartiness, whole-souledness, impetuosity and excitability.”

The head of Pinkerton’s National Detective Agency had reason to feel satisfied with himself that Saturday morning, February 23. His covert mission had begun a little more than a month earlier when Samuel Morse Felton, a kindly-looking Massachusetts man, hired him to investigate threats to Felton’s Philadelphia, Wilmington and Baltimore Railroad from prosecessionist saboteurs. The line was a vital rail link from the North to Washington, over which Federal troops and supplies would travel if war broke out with the South. Pinkerton, whose Chicago agency specialized in tracking and capturing train robbers, arrived in Baltimore on February 1 with a squad of his best detectives. Quickly his undercover operatives infiltrated Baltimore’s secret societies and paramilitary organizations that supported southern secession from the Union. Each agent was identified on intelligence reports they delivered to him by code names or simply with their initials. Using the pseudonym John H. Hutchinson, Pinkerton posed as a chatty stockbroker from Charleston, South Carolina.

It soon became clear to him that the danger was far more serious than railroad vandalism. Practically from the day they arrived, Pinkerton and his detectives began picking up the stories swirling around Baltimore of plots to assassinate the president-elect when he passed through the city. Lincoln, who by tradition remained secluded during his successful 1860 presidential campaign while others stumped for him, had departed Springfield, Illinois, on February 11 for a twelve-day, 1,904-mile, roundabout trip to Washington, D.C., with frequent halts in key states he had won to greet the public and introduce himself to the country before his inauguration the next month as the sixteenth president of the United States. He was scheduled to arrive in Baltimore shortly after noon on February 23.

One of four loyal slave states, Maryland had 90,000 blacks in bondage and a determined minority that favored seceding from the Union. The state, which bordered Washington on three sides, had to be kept open to Union resupply for the nation’s capital to survive. But Maryland was unstable. A tinderbox rife for assassination plotting, Baltimore, the South’s largest and northernmost city, was a logical site to spring the trap. Visitors could reach Washington by train, steamship up the Potomac, or on one of six highways that ran through Virginia or Maryland. The Old Dominion state was far too dangerous to transit through for this president-elect. To reach Washington for his swearing-in, Lincoln had to pass through Maryland and more particularly Baltimore, the key center for railroads that were the most efficient means of moving northern troops in the future to the nation’s capital. The best way for secessionists to nullify the election, perhaps to seize Confederate independence quickly, was to kill Lincoln in Baltimore. Pinkerton and his agents infiltrated the city’s wealthy class, who they suspected would fund such an assassination plot, as well as its lower-class gangs likely to carry out the murder. They discovered what they believed was compelling evidence that when Lincoln changed trains in the city for the Baltimore & Ohio Railroad line that would take him to Washington, a dense and hostile crowd would surround him from which assassins would emerge to shoot or stab him. As near as Pinkerton could determine, the local police planned no escort or if they did have one it would be with disloyal officers sympathetic to the killers.

Pinkerton intercepted Lincoln at Philadelphia’s luxurious Continental Hotel the night of February 21 and briefed him on the assassination threat he believed he had uncovered. Lincoln knew the detective and thought highly of his agency. Outwardly the president-elect refused to appear alarmed by personal threats. But there was evidence he was taking them more seriously than he let on. Lincoln began receiving death threats as early as October 1860, when his election victory seemed certain. After the vote, hate mail from all over the country piled up in Springfield. Warnings came that he would be poisoned. Several packages of tainted fruit arrived from the South. Newspapers were filled with stories of sinister forces that would prevent Lincoln from taking office. Washington was alive with rumors of assassination plots and conspiracies to burn down the city. One report out of New Orleans had a $40,000 bounty placed on his head. Lincoln’s stepmother worried he never would return home alive from his presidency. So did Springfield friends.

It had been a logistical nightmare arranging the president-elect’s travel. There was no direct rail line from Springfield to Washington. Instead, he had to chug along at thirty miles per hour over a hodgepodge of fifteen different lines, some of which were run by powerful railroad executives who sympathized with the South. His protection during the trip was woefully inadequate. There was no federal secret service to guard him. Lincoln refused to have an Army escort, believing it made him look like a warlord. No one traveling with him was even officially designated to be responsible for his security, so protection was handled by a makeshift detail of friends and military men aboard the train. In Baltimore, against a large angry crowd and hostile cops, the puny security detail would be easily overpowered.

Lincoln agreed to Pinkerton’s complex plan to sneak him into Washington ahead of his announced travel schedule while his would-be Baltimore assassins slept. The evening of February 22, the president-elect, with only Lamon to guard him, quietly slipped away from his traveling party of more than a dozen in Harrisburg, where he had delivered an address to the state legislature, and boarded a special Pennsylvania Railroad train that Pinkerton had arranged to take him 110 miles east to Philadelphia. Pinkerton joined the pair in Philadelphia and took them in a carriage shortly after 10 p.m. to the station for Felton’s Philadelphia, Wilmington and Baltimore Railroad on the south side of town, where they boarded the rear of a sleeping car. Kate Warne, one of Pinkerton’s female operatives, had reserved four double berths partitioned off from other passengers, which she told the conductor was for her sick brother.

At 3:30 a.m. on February 23, Lincoln, Pinkerton, and Lamon arrived in Baltimore, where the sleeping car was unhitched and pulled by a team of horses to the Baltimore & Ohio Railroad’s Camden Street Station a mile away. As dawn was about to break, the B&O’s Washington-bound train finally arrived, much to the relief of Pinkerton, who dreaded the thought of the president-elect stranded in a wide-awake Baltimore with just him and Lamon for protection. Lincoln’s sleeper car was hooked up to it for the final thirty-eight-mile leg to Washington.

After his shot of whisky with Lamon, Pinkerton stretched out on the sleeping car’s back platform. The cold wind buffeting his face, he watched as their southbound train sped by quiet hamlets and dingy farmhouses. Pinkerton was not a man given to deep introspection. But it was remarkable, if he ever stopped to think about it, that he had risen from roots as humble as Lincoln’s to reach the point where he was now rescuing a future president.

Pinkerton could trace his line to seventeenth-century Gorbals, a Scottish burgh on the south bank of the River Clyde, annexed by Glasgow in 1661, which by the nineteenth century had become a bustling factory and workshop center for more than 35,000 people living in squalid thatched houses and multistory tenements along narrow streets.

William Pinkerton was a grim-faced muscular man, with a gloomy personality and a modest amount of schooling, who stood about six feet tall and was “straight built,” according to his son Allan. He likely supplemented his falling income as a home handloom weaver by serving as a Glasgow city jail trustee, which gave him some standing in the community. Allan Pinkerton, who was prone to fabricating parts of his biography, claimed that his father died as a police sergeant battling rioters, but that story appears to have no basis in fact. William’s first marriage was to Isabella Stevenson, who bore him seven children (five of whom lived beyond childhood) and who, according to family legend, died after delivering the last one in 1807. In his mid-forties, William married a thirty-three-year-old cotton mill worker named Isabella McQueen, who had Allan and another son, Robert, who survived to adulthood. Allan was born in 1819 in the couple’s third-floor tenement apartment on Muirhead Street. The exact day is in dispute. Biographers have it variously as July 21, August 21, and August 25.

Little can be confirmed about Allan’s childhood. Pinkerton’s later accounts of it are riddled with inaccuracies. He claimed the household was “completely filled with the tensions of two families existing in a few rooms,” but that may not have been the case. William was a stern father, but by the time Allan was five, the children of the first marriage had all left home and only Allan and his brother Robert remained in the apartment. Allan attended elementary school until age nine or ten, when his father died. With a firm grounding by then in reading, writing, and arithmetic he was considered adequately educated for that time. He later regretted not having any more formal schooling and thought he suffered because of it.

After several years of odd jobs for pennies a day, Pinkerton at age twelve decided to apprentice with William McCauley, a Gorbals barrel maker, to learn how to be a cooper. Six years later he had earned a journeyman’s card. By then, he was five feet eight inches tall with powerful shoulders and arms from hours spent each day pounding iron barrel hoops with a ten-pound hammer. But he described himself as a “tramp cooper,” roaming Scotland and northern England the next four years finding short-term work that ended each time with layoffs.

Industrial unrest swept Glasgow by the end of the 1830s, fueled by a downturn in the British economy, with cotton mill owners cutting wages, thousands of their workers striking, and union leaders being marched off to jail. In 1838, Pinkerton became a Chartist, named for a popular working-class movement whose six-point People’s Charter called for democratic reforms and broader suffrage for men. Pinkerton, who became the Glasgow coopers’ representative to the Chartist Convention in Birmingham, joined the grassroots revolt because “I was free in name, but a slave in fact,” he recalled. He came to worship the frail yet charismatic George Julian Harney, a London communist among the Chartist leaders, and became Harney’s strongman as he traveled through Scotland delivering fiery speeches. On November 4, 1839, Pinkerton joined 5,000 men armed with mostly spears and clubs in the Newport, Wales, uprising to free Henry Vincent, an imprisoned Chartist orator. He escaped being among the twenty-two Chartists whom soldiers killed and the sixty-two whom police arrested after scattering the mob with a volley of musket fire.

In April 1841, while organizing a concert at O’Neil’s Public House to raise money for striking spinners in Glasgow, Pinkerton couldn’t take his eyes off fourteen-year-old Joan Carfrae, a bookbinder’s apprentice who was singing soprano in the event. An Edinburgh orphan, Joan had been reared by her aunt, who educated her. She was a kind young girl, who sang in Glasgow’s Unitarian Church on Center Street and was as committed as Pinkerton was to workers’ rights. Allan courted her for almost a year before they married on March 13, 1842, when Joan was fifteen. She may have misled Pinkerton into believing she was eighteen. He was twenty-two.

The next month, Joan shared a filthy cabin with other women and Allan wedged into the crew’s quarters aboard the merchant ship Kent, sailing for America and what the young couple hoped would be a better life. Pinkerton paid for their passage by working as the ship’s cooper. Their first stop was to be Montreal, but storms blew the Kent far off course and she foundered 250 miles south on ice and reefs at Sable Island, southeast of Halifax, Nova Scotia. A lifeboat carried them to shore, where Indian raiders promptly robbed them of the few possessions they carried, including Joan’s wedding ring. In May, they finally reached Montreal with only twenty-five pennies in Pinkerton’s pocket. Allan and Joan found a room in a boardinghouse and Allan scratched out a living in Montreal making beef barrels until he was laid off several months later. Giving up on Canada, the couple planned to book a steamer south to Chicago, but they changed their minds and moved instead to the village of Warsaw, in western Illinois. Calamity struck once more—they were robbed of everything but the clothes on their back—so they decided to return to their original plan and move to Chicago.

Chicago in 1842 was a growing frontier town of 1,200 hardy people and some two dozen businesses, packed along muddy rutted streets with cattle herded on them to slaughterhouses and reeking gutters filled with garbage. Robbie Fergus, an old Glasgow friend who had settled there, let the couple stay in one of his rooms and helped Pinkerton find a job at Lill’s Brewery, at the corner of Pine Street and Chicago Avenue, working for fifty cents a day making beer barrels as a cooper.

Fed up with how little money he took home after a year of slaving away at Lill’s, Pinkerton moved thirty-eight miles northwest to Dundee, a settlement of some three hundred Scots and their dairy farms on the scenic Fox River in Kane County, Illinois. Dundee had a few country stores, a post office, several blacksmith shops, a mill, and two small taverns. Pinkerton built a one-story frame cabin at the edge of the village on a grassy knoll near a wooden bridge spanning the river and became the town’s only cooper. Waking each morning at four thirty and laboring seven days a week, he built the business up with eight apprentices on his payroll by 1847, offering quality work at a lower cost for area farmers fed up with Chicago’s high prices for barrels and churns. In 1846, Joan delivered their first child, William. Five would follow. Pinkerton named them all without consulting her.

A life-changing event occurred in June 1846. Always looking for ways to save money, Pinkerton poled his raft to a small island on Fox River a few miles above Dundee to cut wood for his barrel staves instead of buying them. He discovered hidden in the island’s forest later that night what would turn out to be a band of counterfeiters hammering out coins around a roaring fire. Pinkerton hurried back to Dundee and told Luther Dearborn, Kane County’s sheriff, who together with Pinkerton staked out the campsite for a night. Dearborn eventually brought in a posse and arrested the counterfeiters with their bag of bogus dimes.

Pinkerton became a local celebrity after the bust. Dearborn began dropping by to solicit his advice on cases. The next month, two Dundee merchants, Henry Hunt and Increase C. Bosworth, talked Pinkerton into trying to catch another counterfeiter. Wildcat bank currency was a problem in the rural Midwest. Laws regulating the national currency did not cover the growing number of states and independent institutions that issued banknotes backed by their gold reserves. Unreliable currency flooded the region and counterfeiters made the problem worse by printing phony versions of the bills these institutions issued. Little money circulated in Dundee—a barter system covered most transactions—but one institution that did issue high-quality currency in Kane County was George Smith’s Wisconsin Marine and Fire Insurance Company, which had secured banking privileges in that state and had a branch in Chicago. His bills were nicknamed “George Smith’s money.” The Dundee merchants wanted Pinkerton to catch the scoundrel who had passed at least two phony ten-dollar bills of George Smith’s money in Dundee. Pinkerton, who had never seen a bill as high as ten dollars, met and began ingratiating himself with the man the merchants suspected was the counterfeiter—John Craig, a tall, well-heeled, and swarthy-looking newcomer in his sixties who said he was from Vermont.

For a barefoot cooper in overalls, Pinkerton hatched an elaborate sting to try to catch Craig, eventually showing up with $125 of the merchants’ silver as bait to buy fifty of Craig’s bogus $10 bills. But the trap Pinkerton set ended up failing. The wily Craig, who always had surrogates do the dirty work so he could not be directly linked to the counterfeit money, eventually was arrested but he managed to escape from jail after bribing an officer. When Pinkerton visited the irascible George Smith in Milwaukee to be reimbursed at least for the time he spent running off Craig, the bank president griped but paid, warning that if the upstart cooper ever played detective again without his authorization, he wouldn’t get a dime from George Smith. Pinkerton learned a hard lesson: always have a written contract before you take a case.

Pinkerton moved back to Chicago in 1848. He had become restless and Dundee had grown too conservative for his tastes. After chasing John Craig, he had taken a job on top of his cooper’s business as a part-time Kane County deputy sheriff, but when he ran for sheriff on an abolitionist ticket in spring 1847 and the next year ran as a candidate on the Liberty Party ticket for the state’s constitutional convention, Dundee’s Baptist Church minister fiercely campaigned against him, accusing him of being a drunkard and an atheist. Pinkerton was not a drunkard but he was an atheist. He lost both elections.

In the five years Pinkerton had been away, Chicago had exploded to nearly 30,000 people, with new residential homes, business houses, hotels, and theaters being built, rail connections arriving, and ships lining up at the shores of Lake Michigan. Pinkerton, whose Dundee policing had made him well known around the state, became a deputy sheriff in Cook County, whose seat is Chicago. He built a two-room, clapboard frame house, painted white, on Adams Street near the lakeshore for his family. Pinkerton became the law enforcement agency’s first detective, earning a reputation as a tough, fearless, and honest lawman, which in Chicago could be dangerous. While he walked up Clark Street one night to his home, a pistol-wielding thug he had likely once rousted shot him in the left arm.

Pinkerton remained on the force for about five years. He claimed he resigned because of “political interference,” which may have been the case since the city’s Democratic mayor did not take kindly to officers like Pinkerton who advocated the abolition of slavery. Pinkerton also may have left the Cook County position to pursue more lucrative detective work. The U.S. Post Office gave him a job as a mail agent to probe a rash of mail thefts plaguing the city. He posed as a mail clerk and found that the nephew of the Chicago postmaster, who had been given a sorter’s job with the service, was stealing bank drafts and money orders from envelopes.

Needing more money for his growing family, Pinkerton around 1855, or perhaps earlier, formed with a lawyer named Edward Rucker the North-West Detective Agency and set up a tiny office at 89 Washington Street. Rucker, always a silent partner in the venture, dropped out of the arrangement the next year. Before resigning from official police work, Pinkerton had polled railroad executives on whether he should form a private detective firm. They thought it was an excellent idea. Crime plagued the region and no state or federal law enforcement agency existed. Local police forces often were filled with incompetent or corrupt officers their citizens considered no better than accomplices for the criminal class. Businessmen, who distrusted local cops even more, needed some type of protection and crime detection organization to guard their companies. The agency Pinkerton was forming would be the closest thing to a national investigative organization—his trademark soon becoming “We Never Sleep,” under a drawing of an eye. He adopted the expression “private eye,” which eventually became the nickname for detectives.

From his Chartist background, Pinkerton showed a genius for organizing and attention to detail—but often becoming an ironfisted micromanager and not delegating. He perfected policing and detection techniques sophisticated for the time, such as employing undercover disguises, exploiting the latest technology like the telegraph and photography, and compiling a vast picture gallery of criminals (Pinkerton’s became the largest in the world). He paid his detectives $3 a day, a supervisor cost a client $8 a day, and Pinkerton charged $12 a day for his services. For the comfortable salaries they received, Pinkerton expected his operatives to abide by high ethical standards—an innovation at the time when the public considered most private detectives little different from the criminals they hunted. Pinkerton did not allow his employees to drink, smoke, play cards, or frequent “low dives.” They had to wear “somber dress,” could not cash in on their exploits with newspaper or magazine stories, and were forbidden from accepting rewards for the criminals they caught. That last prohibition helped Pinkerton maintain good relations with police forces throughout the Midwest.

The first man Pinkerton hired for his agency was the talented and patrician George Bangs, who had started out as a reporter and then drifted into police work before Pinkerton spotted him. A tall and handsome man with a commanding presence, Bangs was an efficient business manager as well as a skilled detective and quickly became Pinkerton’s general superintendent. Other men were recruited, like Adam Roche (a pipe-smoking German who had worked on a lumber barge), John White (whom Pinkerton thought adept at catching con men because he looked like one), and John Fox (a talkative New Englander who had been a watchmaker).

Kate Warne, slender, brown-haired, and a widow at twenty-three, barged into Pinkerton’s office one day and announced she wanted to be a detective, arguing that a woman could worm her way into situations males couldn’t and glean valuable information. A startled Pinkerton had never considered a female for detective work, but after mulling it over for a day he decided to hire this graceful and self-assured woman. Warne proved to be a courageous and trusted operative. Men found her fascinating. She became expert at playing roles to entice suspects to divulge their secrets, posing once as a clairvoyant with costume and makeup to convince a superstitious woman to admit to poisoning her brother. Soon Warne headed Pinkerton’s “Female Department,” composed of several women. Some family members suspected that in later years Pinkerton and Warne had an affair.

He took all kinds of cases at the outset—except for divorce and infidelity investigations. He considered them undignified. But Pinkerton was not shy about unconventional methods, such as braying into the night like an angry ghost near the bed of a suspect to scare him into confessing. A Chicago newspaper questioned a $700 bill Pinkerton submitted to the city, which included $139 the paper considered a staggering amount for arresting what must have been a “multitude” of pickpockets. Within a short time Pinkerton had branch offices in neighboring states with agents investigating murders, counterfeiters, and mail thieves. He also started a uniformed guard service to protect Chicago meatpackers. As his reputation spread he began taking on more complicated interstate cases, infiltrating spies to protect companies from their enemies: robbers, thieving employees, and organized labor (he set aside the idealism of his Chartist days to become a well-paid tool of business interests).

A large part of his agency’s income soon came from protecting railroads and the express companies that shipped freight, packages, and money on the trains. The vast railroad expansion of the mid-nineteenth century quickly exposed a serious security weakness for the industry; police could not protect the trains as they traveled from one jurisdiction to another. Six Midwest railroads paid Pinkerton $10,000 annually by 1855 to protect their lines. He signed security contracts with Wells Fargo, American Express Company, and Adams Express Company. His retainer for security work for one company, the Illinois Central Railroad, was drafted by its attorney, Abraham Lincoln, who was impressed with the work Pinkerton did for the company. Pinkerton never said anything about what he thought of the Illinois Central’s lawyer. He became much closer to its vice president, George McClellan, whom he admired greatly.

Pinkerton’s agency soon began attracting nationwide and even international attention. He chased train robbers and spied on conductors suspected of pocketing fares they collected from passengers. For Adams Express, his undercover agents set up an elaborate sting—which included Kate Warne posing as the wife of a shady businessman and John White pretending to be a big-city forger—to catch the Montgomery, Alabama, branch manager, who had stolen $40,000. Pinkerton changed the business’s name to Pinkerton’s National Detective Agency to reflect the fact that his Midwest company was evolving into a national one.

Pinkerton’s aggressive tactics and incorruptibility made him hated by the criminal underworld. But it never cowed him. He found crooks, whom he studied intensely, generally to be an unimaginative lot with predictable patterns, who could not keep their mouths shut about the crimes they committed and who could easily be defeated, he said, by anyone with “a moderate amount of intelligence.”

The champion lawman, however, was a lawbreaker in one respect. Pinkerton routinely aided runaway slaves, a violation of the Fugitive Slave Act that could have landed him in jail if he was caught. He allowed the attic and cellar of his house to be a way station for runaways coming up the Mississippi or Ohio Rivers to reach Canada, he became an emissary for John Brown, who visited his home with runaways, he met Frederick Douglass, and he raised money for the Underground Railroad. He found America’s slaveholding class as repulsive as the “one against which I had rebelled across the ocean,” he wrote. After Brown was captured in the abortive 1859 raid on the federal arsenal at Harpers Ferry, Pinkerton raised money for his legal defense fund.

As the sun rose on February 23, 1861, Pinkerton gave no thought to how Lincoln would be protected once he arrived in Washington. He should have. Remnants of prosecession paramilitary groups that had been openly drilling in Washington remained in the city. At 6 a.m. the B&O train pulled in to the dirty and cheerless Washington Depot with its tower and clock, which stood at New Jersey Avenue and C Street within sight of the Capitol. Buses and hacks lined up at the station’s entrance, their drivers yelling at the top of their lungs to attract the attention of early-morning arrivals who needed rides. Lincoln stood up in the sleeper car, stretched his tall frame, gave a weary smile, and said to no one in particular: “Well boys, thank God this prayer meeting is over.”

No one had slept during the nightlong train ride. It would have been difficult for Lincoln even if he had wanted to. The wooden beds in the rustic sleeping car, partitioned by curtains, were too small for his six-foot-four-inch frame. Most of the time he had sat on a padded bench and whispered an occasional joke to Pinkerton and Lamon to break the silence. He routinely spun stories not only because he thought they were funny or to impart a broader message, but also as a defense mechanism to deflect criticism or questions he did not want to answer. That night the stories may have helped turn his mind off to the strategic catastrophe unfolding before him. As Lincoln’s train headed to Washington, seven southern states had already seceded from the Union and four more would eventually follow. Jefferson Davis had been inaugurated president of the Confederacy and had begun establishing his government in Montgomery, Alabama, ahead of Lincoln forming his in Washington. Lincoln would face 750,000 square miles of his country cleaved away to form a rebel nation controlling most of the federal government’s military assets in that territory. The president-elect was left with aging generals like Army commander Winfield Scott leading a pitifully small force of 1,108 officers (one-third of them from the South) and 15,259 soldiers mostly scattered around the country in outposts watching Indians.

Lincoln was beginning his presidency with a sophisticated clandestine operation—ironic, perhaps, considering he was one of the least experienced men to enter that high office. The son of a poor Kentucky family who was distant from his father, he had only the briefest of formal schooling, which he never was proud of. He was largely a self-taught lawyer, who had served only four terms in the Illinois state legislature and one term in Congress, had failed twice in bids for the U.S. Senate, and had no administrative experience in a senior government position. He cultivated for political purposes the image of a simple frontier “rail splitter,” but disliked the nickname “Honest Abe” (preferring to be addressed as Mr. Lincoln); he was ambitious, and he would assume the presidency not totally unfamiliar with the dark arts of subterfuge and intrigue that Pinkerton practiced.

Lincoln had a slight brush with military service in the 1832 Black Hawk War—no combat but it did give him a taste of leading men. (At one point during that conflict he also spent three weeks in a unit called the Independent Spy Company, which carried out reconnaissance operations.) Often writing political columns under aliases, in 1842 he used one of them to attack an Illinois state auditor in a newspaper. When the angry auditor learned it was Lincoln and challenged him to a duel, Lincoln found a way to back out and came away with a valuable lesson that black propaganda and publishing under a pseudonym could have unintended consequences. He paid close attention to the messaging and mechanics of his few political campaigns. He secretly bought a German-language weekly newspaper to print puff pieces on him for that important voting bloc in Illinois, and during the 1860 campaign for the presidency he had favorable stories about him planted in the press. At the Republican Party’s nominating convention in Chicago, Lincoln’s political team printed duplicate tickets to pack the Wigwam hall with his supporters in order to create the appearance of a groundswell for him. And during the race afterward he was a careful reader and evaluator of political intelligence.

Congressman Elihu Washburne, who had been alerted that Lincoln might arrive early, stood by a pillar on the platform, craning his neck to see if he was among the passengers climbing off the train. The Illinois Republican had funneled back-channel letters from Lincoln to Scott and had organized an informal “Public Safety Committee” to investigate threats to the future president. Washburne finally spotted Lincoln emerging from the rear sleeper car accompanied by two other men. He was wearing an old overcoat with a traveling shawl over his shoulders. To make himself less recognizable during the clandestine trip, Lincoln had left his signature stovepipe hat in Pennsylvania and wore instead a soft felt “Kossuth” hat a New York hatter had given him, which was popular then and looked like a flattened bowler with a wide brim. No one else around the station seemed to recognize the president-elect.

Washburne ran up waving his arm. “How are you, Lincoln!” he shouted. Pinkerton, thinking he was an attacker, jumped in front of the president-elect and delivered a sharp blow with his elbow to the congressman’s chest, causing him to stagger backward. “Don’t strike him, don’t strike him—this is my friend Washburne!” Lincoln said, grabbing the detective by the shoulder. An embarrassed Pinkerton apologized for punching him.

The four men walked quickly out of the depot to the street, where Washburne had a carriage and driver waiting to take them to the Willard Hotel, a mile away. The Lincolns would stay there until the inauguration. The president-elect gazed out the carriage window as they rode over cobblestones, passing by the Capitol’s unfinished steel dome surrounded with scaffolding and derricks, by street vendors setting up stands and shop owners opening their stores for the morning. A shabby stench hung over the city from the odorous B Street Canal and Tiber Creek, which ran through its center.

A block from the Willard, Pinkerton ordered the carriage driver to stop and climbed out with Washburne and Lincoln to walk the rest of the way. Lamon rode ahead with the driver to scout out the hotel’s entrances for their arrival. When they reached the Willard, Lamon told them to take Lincoln through the less crowded ladies’ entrance on the 14th Street side, where he had one of the Willard brothers standing to meet them. When Lincoln arrived in 1861, the Willard Hotel on Pennsylvania Avenue was considered more the center of Washington life than the Capitol or White House. Expanded three years earlier with a six-story addition built on the southwest corner of 14th and F Streets, the hotel had elegant gentlemen’s and ladies’ dining rooms serving as many as 2,500 customers a day, lavish parlors with pianos, sofas, and easy chairs, three large halls, and two broad oak staircases. Low-income clientele took the cheaper top-floor rooms while the well-heeled and foreign dignitaries occupied the better quarters of the lower floors. Now with escalating tensions, northern and southern guests stayed on different floors and were directed to separate exits to avoid clashes.

The hotel management had not expected Lincoln until the afternoon, and parlor number six, where he and his family would stay, was not yet ready, so he was ushered to a receiving room for the moment. Senator William Seward, whom Lincoln had picked to be his secretary of state, arrived shortly and the two men compared notes on the threat that may have existed in Baltimore. Word quickly spread through the hotel that Lincoln had arrived and guests from the drawing rooms began crowding halls to catch a glimpse of the future president. Exhausted, Lincoln retreated to the room the staff finally had ready for him.

Pinkerton also was worn out and checked in to a room, registering as E. J. Allen, for a hot bath and breakfast. Refreshed, he walked over to the telegraph office and sent coded messages that they had made it to Washington to Norman Judd, a Springfield lawyer with Lincoln’s traveling party who had acted as a de facto chief of staff for the president-elect during the trip, and Edward Sanford, an American Telegraph Company executive who had helped with the operation in Pennsylvania. “Plums arrived here with Nuts this morning—all right,” read the one to Sanford. “Plums” stood for Pinkerton. “Nuts” stood for Lincoln.

When he returned to the Willard, Pinkerton found an excited Lamon eager to tell the press about Lincoln’s secret journey. Pinkerton angrily tried to talk him out of that bad idea. The detective still had operatives undercover in Baltimore, whose lives would be put at risk if the papers had the story. Pinkerton also suspected Lamon would spin the story to inflate his role and deflate Pinkerton’s. Later, when the Baltimore operation was wrapped up, Pinkerton talked freely to reporters to make sure he had a prominent place in their accounts. Lamon, who was angling for a plum job in the new administration, wasn’t about to keep quiet. Pinkerton later found him liquored up in the Willard’s bar talking to a New York Herald reporter. He angrily confronted Lamon, reminding him that Lincoln had promised to keep quiet about the operation; he would go to the president-elect to make sure the blackout remained.

Lincoln broke free from a session with a congressional delegation to meet with Pinkerton about 2 p.m. and thank him. He agreed to keep Pinkerton’s role secret. An hour later, Pinkerton climbed aboard the B&O train back to Baltimore to monitor the situation there with his agents until the inauguration, as he told Lincoln he would do. Three hours earlier, at 12:30 p.m., the train bearing Mary Lincoln, her two younger sons, and the rest of the traveling party left behind arrived in Baltimore, whose residents by then knew that her husband had slipped through the city and was safe in Washington. There were conflicting stories about how Baltimoreans reacted to Mary passing through their city. The New York Times reported that a rude and dangerous crowd of thousands greeted Mary at the station; aides kept her locked in a room as thugs, who thought reports of Lincoln already coming through a ruse, roamed through the cars looking for the president-elect. John Nicolay and John Hay, who would become Lincoln’s closest White House aides and had been traveling with Mary, claimed the party encountered “no incivility” in Baltimore. But nobody disputed that the future first lady was still steaming over being left behind.

Pinkerton said Baltimore was “swearing mad” when he arrived about 5 p.m. as a cold rain pelted the city. Assassination conspirators he and his operatives had cultivated in the city were cursing over Lincoln’s escape and vowing to hunt down the spies they thought had infiltrated their organization and tipped him off. Still keeping to his cover as a Charleston broker, Pinkerton pulled a ten-dollar bill out of his purse and gave it to one of the conspirators to help find the traitors.

One of Sanford’s agents arrived from Philadelphia two days later with a copy of the New York Herald, which had run a story naming Pinkerton as part of a secret operation to spirit Lincoln through Baltimore. Furious, Pinkerton telegraphed Judd that Lamon had leaked the story and he needed to shut him up. But Pinkerton also became sloppy with security; he received letters at the Baltimore post office, some possibly from Chicago, with his real name on the envelope.

Pinkerton on March 19 sent Felton his bill. He charged the railroad man $10 a day for his time ($2 less than his usual fee) and $6 a day each for the work that five of his detectives did on the case (which was double what he paid them). It totaled up to $1,400 but he deducted $509.38 for expenses he decided not to charge Felton, bringing the final bill down to $890.62. Pinkerton continued to muscle for recognition, engaging in a long-running feud with New York City police chief John Kennedy, who had sent three undercover officers to Baltimore at the request of Seward to investigate the threat against the president-elect. Pinkerton accused Kennedy, who ran one of the best law enforcement agencies in the country, of trying to hog credit for the operation that took Lincoln through the city. But Pinkerton’s larger problem became a growing political chorus that claimed he averted a threat that never existed.

Newspaper editorials excoriated Lincoln for the cowardly way he had sneaked into Washington. Baltimore police chief George Proctor Kane insisted his force would have provided ample protection. The New York Times reported that he had slipped through Baltimore wearing a Scotch plaid cap and long military cloak—a false story, but one that stuck when cartoonists drew “fugitive sketches” mocking him. Lincoln’s presidency had taken a body blow before it had even begun, with all the hard work of his get-acquainted journey undone in one fell swoop. With just nine days before his inauguration, Lincoln, instead of preparing himself for a difficult presidency, was having to cope with a PR disaster—accused of coming “to the capital like a clown,” as historian Bruce Catton put it, and further sowing misgivings among northern leaders that he was not up to the job.

Pinkerton came under fire as well. Lamon, hardly a fan of the detective, claimed Pinkerton’s operatives swallowed a lot of harmless boasting by hotheads, which Pinkerton then used to concoct a conspiracy in order to drum up business for his agency. “How much longer will the people of this country be the dupes of these private detectives?” railed the Chicago Democrat. Lamon claimed that Lincoln later told him he regretted letting Pinkerton talk him into sneaking through Baltimore. The postwar memoirs of other members of his traveling party suggested that Lincoln realized he had been poorly advised in the matter. Tellingly, Lincoln, a serial storyteller, never told an anecdote or joke about his secret passage through Baltimore, perhaps because he considered it a sore subject. If a plot had existed, many twentieth-century historians have asked, why was no one ever arrested, tried, and punished for it? The known Baltimore plotters—like ringleader Cypriano Ferrandini, a Corsican barber in the city’s Barnum’s Hotel—were all easy to find and the Lincoln administration would soon demonstrate that it was not shy about throwing enemies of the government in jail.

Lamon later recanted somewhat, indicating in a memoir that the Baltimore plot may have been for real. Lincoln also sent mixed signals. Washburne said the Lincoln he picked up at the train station was neither “mortified” nor “chagrined” about how he got to Washington. Near the end of the Civil War, Lincoln told a congressman he thought a plot existed. The fact that Ferrandini and the others weren’t tried does not necessarily mean they were innocent. Baltimore was in a turbulent state in early 1861. It was unlikely federal authorities would have pursued an investigation with war on the horizon and so many other urgent matters to attend to. It was also not a given that the conspirators would have been convicted if they had been arrested. The plotters would have had to have been tried in Baltimore, which would have alarmed its citizens at a time when Lincoln desperately wanted to keep Maryland in the Union. Lincoln also wanted to put the entire episode behind him—not eager for a trial that would bring him more political grief.

How close the alleged conspirators came to carrying out their plan can be argued, but what is not debatable is that the threat of them carrying it out was credible. For Pinkerton to have staged such an elaborate fabrication he would have had to have a lot of detectives in on the scheme, and none of them ever said it was a hoax. Moreover, Kennedy had independently uncovered evidence of the plot. Crowds in Baltimore erupted in anger when they discovered Lincoln had slipped through. Two months later riots, killings, and bridge burnings did occur in Baltimore when a Massachusetts regiment tried to make its way through the city and clashed with a mob. Besides, whether the evidence of a Baltimore plot ultimately proved true “was not the question,” Nicolay and Hay wrote after the war. Lincoln had no right to ignore the danger Pinkerton uncovered. Not only his personal safety but “the fate of the government of the nation” hung in the balance. Lincoln had to take the threat seriously.

The fabrication charges deeply wounded Pinkerton, who until the day he died had no doubt that the Baltimore conspiracy was real and his operation averted a catastrophe. In the 1940s Pinkerton’s family lobbied everyone from the New York Times to FBI director J. Edgar Hoover to recognize his role in preventing the assassination of Lincoln.

Table of Contents

Cast of Characters xi

Time Line of Major Events xvii

Maps xix

Note to Readers xxiii


1 Allan Pinkerton 3

2 George Sharpe 23

3 Elizabeth Van Lew 29

4 Lafayette Baker 39

5 Secret Service 47

6 Bull Run 55

7 The Ohio Department 64

8 Washington 80

9 "Enemies of the State" 102


10 Richmond 123

11 "I Have the Honor to Report" 141

12 The Peninsula Campaign 157

13 Second Bull Run 194

14 Antietam 207

15 Fredericksburg 221


16 "The Great Game" 233

17 Chancellorsville 249

18 Gettysburg 267


19 Muckraker 313

20 The Richmond Ring 322

21 Ulysses S. Grant 340

22 The Richmond-Petersburg Campaign 354


23 Richmond's Fall 379

24 Assassination 399

25 Peace 415

Acknowledgments 445

Selected Bibliography 449

Source Notes 475

Index 571

Photo Credits 595

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