Military history



John Brown’s effort was peculiar. It was not a slave insurrection. It was an attempt by white men to get up a revolt among slaves in which the slaves refused to participate.… That affair, in its philosophy, corresponds with the many attempts, related in history, at the assassination of kings and emperors. An enthusiast broods over the oppression of a people till he fancies himself commissioned by Heaven to liberate them. He ventures the attempt, which ends in little else than his own execution.

—ABRAHAM LINCOLN at Cooper Union, February 27, 1860

THE KNOCK ON THE DOOR came at 4:30 A.M. on March 11, 1859. Allan Pinkerton swung open the door in his nightshirt, a revolver in hand. The sight that greeted him was all too familiar: a group of eleven newly liberated slaves—men and women alike—in tattered clothing and worn boots, exhausted after an arduous trudge across miles of frozen prairie. One of the women cradled a cold, hungry baby in her arms, having given birth on the journey, and she and her fellow travelers, according to one man who helped them on their way that night, formed “a portrait of human misery.”

Pinkerton stepped back and waved the travelers inside, his eyes darting up and down the street before he shut the door behind them. His wife, Joan, still in her nightclothes and robe, set to work preparing breakfast while Pinkerton turned to the man who had brought them north after a raid in Missouri. Even in his soiled, ragged clothing, the visitor retained the stern and fiery appearance of an Old Testament prophet. Tall and angular, he carried himself with a crisp, military air. He had piercing blue-gray eyes under bristling brows, and a flowing white-gray beard framing his sharp, craggy features. Pinkerton stepped forward and grasped his hands. “John Brown,” he said. “We had not expected you, but you are welcome all the same.” The notorious fire-and-brimstone abolitionist returned Pinkerton’s greeting with uncommon warmth—“more than that,” said a friend, he embraced the detective as “brother to brother.”

“Old Brown of Osawatomie,” as he was known at the time, was no stranger to Pinkerton’s home on Adams Street. “John Brown,” Pinkerton would write, “was my bosom friend, and more than one dark night has found us working earnestly together in behalf of the fleeing bondsman who was striving for his liberty.” Not all abolitionists had such high regard for Brown, who advocated a “holy crusade” of armed insurrection as a means to end slavery. Abraham Lincoln would label him a “misguided fanatic.”

The abolitionist John Brown, Allan Pinkerton’s “bosom friend.” Courtesy of the Library of Congress

Pinkerton had come to know Brown at the time of the “Bleeding Kansas” crisis, a series of shockingly brutal clashes between abolitionist forces and pro-slavery “Border Ruffians” over the issue of whether Kansas would enter the Union as a free or slave state—a prospect that threatened to tip the balance of political power. In May 1856, Brown had led a raid into Kansas that left five pro-slavery Southerners dead—hacked to death with swords—an act he characterized as a response to recent violence against abolitionists, and a signal of his unflinching stand against the weak and conciliatory policies of the North. The “Pottawatomie Massacre,” as the assault came to be known, established Brown’s grim resolve to tear apart the increasingly fragile relations between North and South.

Now, warming his hands at Pinkerton’s fire, Brown appeared more than ever to be, as Frederick Douglass described him, a man whose “soul had been pierced with the iron of slavery.” For all his ferocious passion, he came to Pinkerton as a wanted outlaw. The governor of Kansas was reported to have offered a three-thousand-dollar reward for his capture. President Buchanan had ordered his arrest, and had added $250 to the bounty. As one newspaper declared, John Brown had become “the most notorious brigand our land has yet produced.”

Brown’s fugitive status did nothing to undercut the support offered him by Pinkerton, America’s top lawman. If anything, Pinkerton’s growing fame had added heat to his convictions. Even as he gained national renown as a tough and ruthlessly efficient lawman, Pinkerton continued to operate as an agent of the Underground Railroad. Having established himself as a detective, albeit a private one, Pinkerton found that his clandestine activities now carried a serious threat of legal consequences. The Fugitive Slave Act of 1850, intended to bolster earlier legislation that had fallen into disuse, sought to force federal marshals and other officers of the law in the free states to return runaway slaves to their masters. The new law overturned many of the “personal liberty laws” that had been passed in Northern states, and carried a one-thousand-dollar fine for any official who failed to enforce it. At the same time, any person charged with providing food or shelter to a fugitive would be subject to six months in prison and a one-thousand-dollar fine. As the stakes rose, Pinkerton found that he had become a lawbreaker with a badge—“half horse and half alligator,” in Edward Sanford’s phrase. The contradiction did not trouble him. “I have not a single regret for the course I then pursued,” he wrote in later years. To Pinkerton, John Brown was a hero to be emulated, a courageous figure “who almost single handed threw himself into a fight against the Nation.” So long as Brown was in Chicago, Pinkerton made sure he would not fight alone.

Pinkerton’s two-room clapboard house on Adams Street was now crowded with children, and not as well-suited to Underground Railroad traffic as the cooperage in Dundee had been. There were two sons, twelve-year-old William and ten-year-old Robert, and two younger daughters, Joan—born in 1855 and named after her recently deceased older sister—and the sickly Belle. Even so, Joan Pinkerton worked tirelessly to feed and clothe a steady stream of fugitives, who sometimes appeared in such great numbers that she was forced to find room in the cramped space beneath the floorboards and in the half attic below the roof. When the house overflowed, she enlisted friends and neighbors into the cause. Often, when her husband’s detective work took him away from home for long stretches of time, the duty of seeing the runaways safely on to their next destination fell to her. She would have been barely twenty-one years old when the family took up residence on Adams Street, but she threw herself into the struggle, according to one Chicago abolitionist, “as vigorously as did her husband.”

With John Brown’s latest unannounced arrival, the Pinkertons set to work once again. Joan gathered fresh clothing while her husband took the fugitives who would not fit under their roof and “got them under cover” with sympathetic friends. Brown himself was taken to the home of John Jones, a self-educated black man who was campaigning tirelessly against the state’s restrictive “Black Laws.” Jones listened along with Pinkerton as Brown informed them that he had arrived in Chicago “without a dollar” and could not continue his journey without financial help. Both Jones and Pinkerton pledged to do what they could. “There is a Democratic meeting in the city today,” Pinkerton said. “I’ll go down and make them give me enough money to send you and these slaves to Canada.”

Pinkerton recalled that he left the house in a “determined frame of mind,” but he soon realized that his plan had a serious flaw. The Democratic meeting he had mentioned was, in fact, a session of the Chicago Judiciary Convention. Although many of the participants would undoubtedly be sympathetic to the plight of Brown’s runaways, few of them would want to pledge support openly in a legal forum. Pinkerton made some concession to the delicacy of the situation by declining to make the request himself. “I was too well known as being an anti-slavery man,” he said, “and I thought my absence from the meeting would be the best thing.” Instead, he dispatched a pair of friends to circulate what he called a “subscription list” among the delegates. When they returned without a single donation, however, Pinkerton took the matter into his own hands. “I decided that I must have the money,” he said. “I was willing to pay something myself but I could not pay the whole.”

Pinkerton’s new tactic was nothing if not direct. Bursting into the meeting hall, he jumped to the stage and motioned for silence. “Gentlemen,” he began as a stunned silence fell over the room, “I have one thing to do and I intend to do it in a hurry. John Brown is in this city at the present time with a number of men, women and children. I require aid, and substantial aid I must have. I am ready and willing to leave this meeting if I get this money; if not, I have to say this. I will bring John Brown to this meeting and if any United States Marshal dare lay a hand on him he must take the consequence. I am determined to do this or have the money.” Folding his arms, Pinkerton stepped back and waited.

For several moments, the audience of “astonished jurists” simply stared at Pinkerton in uncomfortable silence. Then, with a conspicuous clearing of the throat, a young politician rose and made his way forward, holding out a fifty-dollar bill. With a curt nod of thanks, Pinkerton took off his hat and held it out. One by one, the others formed a line and filled the hat with bills. Within minutes, Pinkerton had collected nearly six hundred dollars. When the last man had passed, Pinkerton inclined his head. “Thank you, gentlemen,” he said. Placing the hat back on his head, he left the hall without another word.

Later that afternoon, Pinkerton and his elder son, William, collected John Brown and his fugitives from the various homes where they had been lodged the night before and prepared to send them on their way. Pinkerton made arrangements with railroad superintendent C. G. Hammond—“a friend to me and also to the colored people”—to have a special passenger car readied at the Chicago depot. As a grateful John Brown took his leave, he turned and offered a warm farewell, along with a pregnant word of warning: “Friends, lay in your tobacco, cotton and sugar because I intend to raise the prices.” When the abolitionist was safely aboard the train, Pinkerton laid a hand on his son’s shoulder. “Look well upon that man,” he said. “He is greater than Napoleon and just as great as George Washington.”

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THIS OPINION REGARDING JOHN BROWN would be sorely tested in the months to come. Though Pinkerton had received strong support from Hammond and other powerful railroad men, not all of his colleagues were so sympathetic to the abolitionist cause. One of Pinkerton’s closest friends during these years was the vice president and chief engineer of the Illinois Central, a young West Point graduate named George Brinton McClellan. Pinkerton and McClellan were an unlikely pair. In contrast to the rough-hewn Pinkerton, McClellan was sleek, handsome, and dashing, and had led something of a charmed life. Born in Philadelphia in 1826, McClellan had entered the University of Pennsylvania at age thirteen, then transferred to West Point two years later, graduating second in his class. Upon leaving the academy, he served with distinction in the Mexican-American War, even performing reconnaissance missions for Lt. Gen. Winfield Scott, a close family friend. Following the war, McClellan joined Randolph Marcy’s expedition to discover the sources of the Red River, only to find upon his return that all the members of the expedition had been given up for dead. The following year, he put his engineering skills to work for Secretary of War Jefferson Davis, exploring possible routes for the transcontinental railroad. In 1855, at the height of the Crimean War, McClellan was dispatched as an official observer of the European armies, later producing a manual on cavalry tactics and a design for a “McClellan saddle,” which became standard U.S. Army issue.

When Pinkerton met him in 1857, McClellan had resigned his military commission, capitalizing on his engineering and railroad experience to secure a lucrative position with the Illinois Central. Though McClellan was seven years younger than Pinkerton, his remarkable catalog of achievements made a forceful impression on the detective, who adopted the young officer as a mentor and role model. Soon enough, their relationship would take a new shape on the battlefields of the Civil War, amid lasting controversy. To the end of his life, Pinkerton would be one of McClellan’s staunchest supporters, declaring himself “proud and honored in ranking him foremost among my invaluable friends.” In terms of political beliefs, however, it is difficult to understand how the seeds of that bond were sown so deeply during their early association in Illinois. Many of McClellan’s views would have struck Pinkerton as shortsighted and timid. McClellan had no particular sympathy for the institution of slavery, and he hoped to improve the condition of “those poor blacks,” but there were clear limits to his resolve. As he told his wife, “I will not fight for the abolitionists.” Even so, Pinkerton embraced him as a kindred spirit. “From its earliest incipiency,” the detective wrote, his working relations with McClellan had been of “the most agreeable and amicable nature.”

Pinkerton was oddly silent about another of his Illinois Central colleagues of this period. Like Pinkerton, Abraham Lincoln was on retainer with the railroad during these years, and the career of the circuit-riding lawyer—like the detective’s—was inextricably linked to the fortunes of the company. Having returned to practice law in Springfield after serving a term in the U.S. House of Representatives, Lincoln often found himself engaged in the legal issues arising from the rapid spread of the railroads across the state, and by the mid-1850s the bulk of his practice was devoted to railroad law.

George McClellan recalled crossing paths with Lincoln on many occasions during these years. “More than once I have been with him in out-of-the-way county-seats where some important case was being tried,” wrote McClellan, “and, in the lack of sleeping accommodations, have spent the night in front of a stove listening to the unceasing flow of anecdotes from his lips. He was never at a loss, and I could never quite make up my mind how many of them he had really heard before, and how many he invented on the spur of the moment. His stories were seldom refined, but were always to the point.”

Whatever his personal feelings may have been, McClellan made his political views clear during the fateful election campaign of 1858, when Lincoln, as the candidate of the newly formed Republican party, challenged incumbent Stephen Douglas for his seat in the U.S. Senate. McClellan and many other Illinois Central men threw their support behind Douglas, a fact that made itself felt during the famous series of debates that decided the contest. As the candidates had agreed to meet in seven different congressional districts, a great deal of travel on the Illinois Central was required. “At all points on the road where meetings between the two great politicians were held, either a special train or a special car was furnished to Douglas,” noted Lincoln’s friend Ward Hill Lamon, “but Lincoln, when he failed to get transportation on the regular trains in time to meet his appointments, was reduced to the necessity of going as freight.” Lamon recalled one ignominious occasion when a freight car carrying Lincoln was shunted off the main track to allow Douglas’s special to thunder past. “The passing train was decorated with banners and flags, and carried a band of music which was playing ‘Hail to the Chief.’ As the train whistled past, Mr. Lincoln broke out in a fit of laughter and said, ‘Boys, the gentleman in that car evidently smelt no royalty in our carriage.’”

At times, Lincoln left a similar impression with the gentlemen in his own car. One passenger who traveled along with him to a debate was startled by the “uncouth, not to say grotesque” appearance of the candidate: “That swarthy face, with its strong features, its deep furrows, and its benignant, melancholy eyes, is now familiar to every American [but] at that time it was clean-shaven and looked even more haggard and careworn than later, when it was framed in whiskers. On his head he wore a somewhat battered stovepipe hat. His neck emerged, long and sinewy, from a white collar turned down over a thin black necktie. His lank, ungainly body was clad in a rusty black frock-coat with sleeves that should have been longer; but his arms appeared so long that the sleeves of a ‘store’ coat could hardly have been expected to cover them.”

It is likely that Pinkerton also crossed paths with Lincoln at some stage during his travels on the Illinois Central, but if so, he did not record it. Pinkerton did, however, follow the debates closely. “The famous contest absorbed public attention throughout the country,” he recalled. “The two candidates indulged in open discussions of public policy, which were remarkable for their brilliancy and for the force and vigor with which their different views were uttered. It was during this canvass that Mr. Lincoln made the forcible and revolutionizing declaration that: ‘The Union cannot permanently endure half slave and half free.’”

In fact, Lincoln first made the famous statement while accepting his party’s nomination at the start of the race: “A house divided against itself cannot stand. I believe this government cannot endure, permanently, half slave and half free. I do not expect the Union to be dissolved—I do not expect the house to fall—but I do expect it will cease to be divided. It will become all one thing or all the other.” Lincoln went on to warn that recent shifts in national policy, including the Dred Scott decision and the Kansas-Nebraska Act, would lead to the spread of slavery throughout the Union if left unchecked.

Even Lincoln’s closest allies recognized that these sentiments, which suggested that conflict between the North and the South was inevitable, sounded a note that was far too pointed and clamorous for the times. “It is true,” said William Herndon, Lincoln’s law partner at the time, “but is it wise or politic to say so?”

Though Lincoln ultimately went down to defeat in the Senate race, his ideas—and the eloquence with which he expressed them—captured the attention of the nation, raising him to national prominence. Lincoln, wrote Herndon, had now become centrally entwined in the issues facing the nation. “His tall form enlarged,” said Herndon, “until, to use a figurative expression, he could no longer pass through the door of our dingy office.”

Lincoln’s increasing prominence signaled what Pinkerton called “a growing sentiment of abolitionism throughout the North,” which, in turn, “aroused the advocates of Slavery to a degree of alarm.” As a result, the new year of 1860 “opened upon a scene of political agitation.” In February, at Cooper Union in New York, Lincoln attempted to elaborate his opposition to slavery while offering reassurance to fractious elements in the South. While he insisted that slavery was “an evil not to be extended” into the new territories of the West, Lincoln acknowledged that the institution was protected by the Constitution where it already existed. He urged his fellow Republicans to “calmly consider” the demands of the Southern states and to “yield to them if, in our deliberate view of our duty, we possibly can.” The address ended on a soaring note: “Neither let us be slandered from our duty by false accusations against us, nor frightened from it by menaces of destruction to the government nor of dungeons to ourselves. Let us have faith that right makes might, and in that faith, let us, to the end, dare to do our duty as we understand it.”

The speech received a rapturous reception and helped to establish Lincoln in the East as a possible contender in the upcoming presidential contest. “Mr. Lincoln is one of Nature’s orators,” wrote Horace Greeley, “using his rare power solely and effectively to elucidate and to convince, though their inevitable effect is to delight and electrify as well.” Though he had not yet declared himself as a candidate for the Republican presidential nomination, his aspirations were becoming clear. “I will be entirely frank,” Lincoln admitted to a friend. “The taste is in my mouth a little.”

*   *   *

BY THAT TIME, tensions had been further inflamed by John Brown’s abolitionist crusade, raising what Pinkerton called “a spirit of fierce opposition in the minds of the Southern leaders.” On October 16, 1859—seven months after Pinkerton had put him on a train in Chicago—John Brown led his notorious raid on the federal arsenal at Harper’s Ferry, Virginia, in the hope of sparking a slave revolt throughout the South. Brown’s tiny force of eighteen men was quickly overwhelmed by a detachment of marines under the command of Col. Robert E. Lee, and six weeks later—on December 2, 1859—Brown went to his death on a scaffold in Charles Town, Virginia. “I am waiting the hour of my public murder with great composure of mind, & cheerfulness,” he had written to his family a few days earlier, “feeling the strongest assurance that in no other possible way could I be used to so much advance the cause of God; & of humanity.”

During the long weeks that Brown spent awaiting execution, there were many rumors to the effect that armed supporters would descend from the North to liberate him and bear him back in triumph. In a memoir written nearly twenty-five years later, Pinkerton would offer his thoughts on the matter: “[H]ad it not been for the excessive watchfulness of those having him in charge, the pages of American history would never have been stained with a record of his execution.” These words have been taken by some to suggest that Pinkerton himself planned to rescue Brown from his prison cell, and it has even been reported that he traveled to Harper’s Ferry with the intent of thwarting the execution order. There is no firm evidence of this, and Pinkerton himself would likely have waved off the speculation. He admitted only to having been “unceasing” in his efforts to win a stay of execution.

Then as now, John Brown was a controversial and divisive figure; Abraham Lincoln’s “misguided fanatic” was Allan Pinkerton’s “bosom friend.” Even allowing for Pinkerton’s lifelong opposition to slavery, his unflinching support of Brown’s methods is difficult to reconcile with his dedication to upholding the law. His complaint of “excessive watchfulness” on the part of Brown’s jailers must be counted as extraordinary, coming from a professional watchman whose logo was an unblinking, hypervigilant eye. Though Brown’s death was mourned throughout the North with black bunting and prayer meetings, many added a note of remorse over the abolitionist’s many acts of horrific violence. Pinkerton entertained no such qualms. The man who had marched with the physical-force Chartists in his younger days believed that violence was, at times, a necessary tool for effecting social change. As he so often said, “The ends justify the means, if the ends are for the accomplishment of Justice.”

The “Eye” had its blind spots.

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