Military history



Should that little craft fall into the hands of pirates, one broadside from the Pennsylvania four-decker will clear the road to Washington. Lincoln, if living, will take the oath of office on the steps of the National Capitol on the 4th of March. My State will guarantee him a safe passage to the White House!

—SENATOR SIMON CAMERON of Pennsylvania (later Lincoln’s first secretary of war) on the prospect of Maryland’s secession, January 1861

PINKERTON LOST NO TIME. Felton’s letter landed on his desk on January 19, a Saturday. The detective set off within moments, flashing one of the many courtesy railroad passes he carried as he hopped aboard the next available train. He reached Felton’s office in Philadelphia only two days later, an impressively rapid response for the time.

Felton had only hinted at the scope of the problem in his letter. Now, as Pinkerton settled into a chair opposite Felton’s broad mahogany desk, the railroad president spelled out the details. According to Miss Dix and other reliable sources, he explained, there was a plot afoot among “the roughs and secessionists of Maryland” to destroy the Philadelphia, Wilmington and Baltimore Railroad. If successful, Washington might well fall into the hands of “rebel insurgents.”

Shocked by what he was hearing, Pinkerton listened in silence. For all his commitment to the abolitionist cause, he had been slow to grasp, as he later admitted, that the country stood at the brink of war. “I entertained no serious fears of an open rebellion, and was disposed to regard the whole matter as of trivial importance,” he explained. “I was inclined to believe that with the incoming of the new administration, determined or conciliatory measures would be adopted, and that secession and rebellion would be either averted or summarily crushed.” Felton’s plea for help, the detective said, “aroused me to a realization of the danger that threatened the country, and I determined to render whatever assistance was in my power.”

For the moment, the detective needed time to consider how to attack the problem. Pinkerton and his operatives had thwarted every imaginable type of train robbery by this time, but never a “deliberate and calculated design” to disrupt a railroad for political reasons. As he reviewed the situation from Felton’s office in Philadelphia, the full weight of the dilemma became clear. Much of Felton’s line was on Maryland soil. In recent days, four more states—Mississippi, Florida, Alabama, and Georgia—had followed the lead of South Carolina and seceded from the Union. Louisiana and Texas would soon follow. Maryland had been roiling with anti-Northern sentiment in the months leading up to Lincoln’s election, and at the very moment that Felton poured out his concerns to Pinkerton, the Maryland legislature was debating whether to join the exodus.

There was little reason to hope that the Old Line State would vote to remain in the Union. In the November election, several Maryland counties had recorded only a single vote for Lincoln, and in two districts he had received no votes at all. Even these meager showings stirred indignation. When a band of six intrepid Republicans in Charles County was found to have cast their votes for Lincoln, angry neighbors ordered them to pack up and leave.

The importance of Maryland, with the Mason-Dixon line squaring off its northern and eastern borders, was obvious to all. It now seemed inevitable that Virginia would secede, and many assumed that Maryland would automatically follow its neighbor. The previous year, a joint committee of the Maryland legislature had responded to the first stirrings of secession in South Carolina with a forceful resolution of support: “[S]hould the hour ever arrive when the Union must be dissolved,” it stated, “Maryland will cast her lot with her sister states of the South and abide their fortune to the fullest extent.” If Maryland made good on this promise and pledged her loyalties to the South, Washington would be hemmed in by secessionist territory and entirely cut off from the North. In that case, as General Scott had suggested to Felton, the federal government might have to abandon its capital city and reestablish itself in Philadelphia or New York.

With the Virginia General Assembly calling for a vote on secession, it appeared that Maryland’s decisive moment was at hand. “The people of the District are looking anxiously for the result of the Virginia election,” noted Frederick Seward, who had joined his father in the capital. “They fear that if Virginia resolves on secession, Maryland will follow; and then Washington will be seized. Meantime the anxiety of the citizens is almost ludicrously intense.”

Pinkerton grasped at once that Felton’s “great connecting link” between Washington and the North must be kept open at all costs. If war came, Felton’s PW&B would be a vital conduit of troops and ammunition. The problem, as Felton explained, was the line’s extreme vulnerability at the many points where it crossed over water. The wooden railroad bridges spanning Maryland’s Gunpowder River and smaller streams could be easily demolished, perhaps even at the moment that a train entered the span. The danger was even greater at Havre de Grace, at the headwaters of Chesapeake Bay, where the line traversed a mile-wide expanse of the Susquehanna River. Although a single-track bridge was under construction, it would not be completed for another five years. In the meantime, railcars arriving at Havre de Grace were uncoupled and placed on ferryboats, which shuttled them across to the opposite bank, a slow and painstaking process and one that could easily be scuttled. As soon as the rumors of sabotage reached his ears, Felton understood that any attack would most likely come at one of these crossings.

For all their concern about the railroad, both Felton and Pinkerton appear to have been blind, at this early stage, to the possibility of violence against Lincoln. They understood that the secessionists sought to prevent the inauguration, but they had not yet grasped, as Felton would write, that if all else failed, Lincoln’s life was to “fall a sacrifice to the attempt.” Instead, as Felton recalled, he did nothing more than supply “a few hints” before Pinkerton set to work. The full degree of peril was beyond his imaginings; “The half,” he admitted, “had not yet been told.”

In this climate of rumor and uncertainty, Pinkerton accepted the commission with a somewhat blinkered view of what was at stake. For the moment, his only concern was the protection of Felton’s railroad. He returned to Chicago to consider the problem, drawing up a seven-page report with recommendations on how to proceed. His proposal made it clear that the situation was changing moment by moment, and that as of yet there had been no tangible proof of a threat against Felton’s line.

“Should the suspicions of danger still exist,” Pinkerton wrote, he would assemble a team of operatives and dispatch them at once to “the seat of danger” in Maryland. Once there, they would assess the risk and attempt to confirm the truth of the plot against the railroad. If successful, Pinkerton and his operatives would go undercover to “become acquainted” with the plotters. In this way, they would soon “learn positively who the leading spirits are that would be likely to do theActive Labor.” With this information in hand, Pinkerton could take whatever steps were necessary to thwart the design, either by arresting the plotters or by heightening security at the intended point of attack.

In many respects, the plan Pinkerton presented to Felton was a simple variation on the template he had been using for years, whether pulling shifts as a mail “piler” at the Chicago post office or assigning Kate Warne to pose as the wife of a forger. As Pinkerton explained to Felton, it would be necessary to keep the suspects under the tightest possible surveillance—“an unceasing Shadow,” as he called it—in order to worm out their secrets. This meant placing men in saloons, hotels, and billiard halls to catch the suspects in unguarded moments, when they would be most likely to spill their secrets.

From the outset, Pinkerton realized that he would be racing the clock. If the plotters intended to disrupt Lincoln’s inauguration—now only five weeks away—it was evident that any attack would come soon, perhaps even within days. Given this time constraint, Pinkerton worried that his usual methods would prove ineffective. “The only danger which I perceive to our operating is in the short time we have to work in,” he explained. “Our operations are necessarily tedious—Nay, frequently very slow.” This was to be expected, he said, because the success of his technique relied upon “attaining a controlling power over the mind of the suspected parties,” as when Kate Warne had persuaded Nathan Maroney’s wife to disclose the location of the stolen money. In such cases, however, Pinkerton had had the luxury of time. The capture of Maroney had unfolded at a stately pace over several months. By contrast, Felton’s case would be a wind sprint.

Accordingly, Pinkerton planned to tackle Felton’s problem with an unusually large team of detectives. “Had I plenty of time to work in, I might probably be able to ascertain all that you require with two or three operatives,” he explained. As matters stood, however, “the time is too brief for me to work safely in this manner.” To have any chance of success, he would have to send a wave of men flooding across Maryland, so as to “attack on every point we can find.”

Pinkerton closed his long letter to Felton by urging him to keep the matter entirely confidential, since any indiscretion would likely expose his detectives to danger. “Our strength lays in the secrecy of our movements,” he warned. “As I have before remarked, Secrecy is the Lever of any success which may attend my operations, and as the nature of this service may prove of a character which might to some extent be dangerous to the persons of myself, or any operatives, I should expect that the Fact of my operating should only be known to myself or such discreet persons connected with your Company as it might be absolutely necessary should be entrusted.” Experience had taught Pinkerton that Felton would not be able to keep the matter entirely quiet, so he added a final heartfelt plea: “But on no conditions would I consider it safe for myself or my operatives were the fact of my operating known to any Politician—no matter of what school, or what position.” Possibly this remark struck Felton as a gratuitous swipe, but, in fact, Pinkerton’s distrust of politicians was well founded. He had dealt with shady elected officials for more than a decade, beginning with the corrupt jailer who had released John Craig at the close of his first case. As a result, Pinkerton had learned to play his cards close to the vest.

Felton agreed at once to give his full support and financial backing to Pinkerton’s plan, and the detective departed immediately for “the seat of danger” with a crew of top agents. To a casual observer, Pinkerton and his team would have looked like an ordinary group of travelers as they boarded the train in Chicago that day. The English-born Timothy Webster, with his bright blue eyes and dark, wavy hair, appeared to be just another attentive husband helping his young wife navigate an unsteady set of wooden platform steps. When the compartment door closed behind them, however, the pair quickly separated and took seats on opposite benches. Webster, a married man, was simply playing a role. The young woman was actually a twenty-four-year-old beauty named Hattie Lawton, a recent addition to Kate Warne’s so-called Female Detective Bureau, who would pose as Webster’s bride in the days ahead. “Her complexion was fresh and rosy as the morning, her hair fell in flowing tresses of gold,” Pinkerton wrote of her. “She appeared careless and entirely at ease, but a close observer would have noticed a compression of the small lips, and a fixedness in the sparkling eyes that told of a purpose to be accomplished.”

Kate Warne was also at Pinkerton’s side that day, preparing to play her signature role of the Southern belle with a kindly nature and a sympathetic ear. She had become one of Pinkerton’s most trusted confidants by this time, and it is likely that the two of them spent much of the journey conferring over maps and case files, laying plans for the task ahead. Close at hand was another new recruit, Harry Davies, a fair-haired young man whose ruddy, open face and unassuming manner belied a razor-sharp mind. Davies had traveled widely, spoke many languages, and had a gift for adapting himself to any situation. He had trained as a Jesuit priest, Pinkerton noted, which lent him an “insinuating manner” that proved useful in dealing with sinners. Best of all from Pinkerton’s perspective, Davies possessed “a thorough knowledge of the South, its localities, prejudices, customs and leading men, which had been derived from several years residence in New Orleans and other Southern cities.”

As his team headed east, Pinkerton seized the chance to get the lay of the land. “I took passage on one of the trains of the road, intending to see for myself how affairs stood, and to distribute my men in such a manner as to me seemed best,” he said. “I resolved to locate my men at the various towns along the road, selecting such places where, it was believed, disaffection existed.” Not surprisingly, the signs of political unrest grew more pronounced as the train pushed toward Maryland and crossed the Mason-Dixon line. At Havre de Grace, the vital crossing point of the Susquehanna River, Pinkerton and his operatives mingled among the locals and heard open expressions of hostile intent. When the train pulled away, a Pinkerton man was left behind to conduct further observation.

Across the river in Perrymansville, twenty-seven miles outside of Baltimore, Pinkerton found an even more intensely warlike mood. The village had long been a hub of railroad workers, but the Fort Sumter crisis had transformed it into a staging area for a makeshift unit of armed cavalry. Pinkerton soon realized that these freshly minted soldiers, though “professedly sworn to protect the railroad,” had a different agenda. “Under the influence of bad men the secession movement had gained many supporters and sympathizers,” he noted. “Loud threats were uttered against the railroad company, and it was boastfully asserted that ‘no damned abolitionist should be allowed to pass through the town alive.’” Though he heard much talk of this kind, Pinkerton knew better than to take such pronouncements at face value. “I have always found it a truism that ‘a barking dog never bites,’” he said, “and although I had but little fear that these blatant talkers would perform any dangerous deeds, I considered it best to be fully posted as to their movements.” Accordingly, Pinkerton made a snap decision to post Timothy Webster in Perrymansville. Webster would look for work among the railroad workers, while Hattie Lawton, in her role as his wife, would seek out “useful friendships” among the women of the community. After a few last-minute arrangements, Pinkerton took his leave of the two operatives and pressed on toward Baltimore, where Felton’s line terminated.

As Pinkerton’s train rolled into Baltimore during the first week of February, the detective observed that the mood of opposition to Lincoln’s inauguration became “manifestly more intense.” Pinkerton took rooms at a boardinghouse on Howard Street, near the Camden Street train station, and he and his remaining operatives fanned out across the city, mixing with crowds at saloons and restaurants to listen to the “grumblings and grouses” of the citizenry. “I soon found that the fears of the railroad officials were not wholly without foundation,” he reported, but he insisted that he had no firm evidence of imminent danger. Even so, the depth of secessionist feeling in Baltimore persuaded him that the possibility of some kind of organized plot was very real. “The opposition to Mr. Lincoln’s inauguration was most violent and bitter,” he wrote, “and a few days’ sojourn in this city convinced me that great danger was to be apprehended.”

It was inevitable that Pinkerton’s focus should come to rest on Baltimore. The city, as one of Lincoln’s advisers would note, was “the back door of the National Capital.” Three separate rail lines converged to form a hub at the center of the city, creating a choke point for all passenger and freight traffic moving through the region. Felton’s brick-fronted depot on President Street was the southern terminus of his Philadelphia, Wilmington and Baltimore Railroad; roughly a mile to the south was the Baltimore and Ohio line’s Camden Street Station, running south to Washington; and lying between the two, half a mile to the west, was the Calvert Street Station of the Northern Central line, running up to Harrisburg, Pennsylvania. So long as these three rail lines remained in operation, Baltimore would have unparalleled strategic importance in the event of war.

At the time, Baltimore had a population of over 200,000—nearly twice that of Pinkerton’s Chicago—making it the nation’s fourth-largest city, after New York, Philadelphia, and Brooklyn, which at that time was a city in its own right. As a major port, Baltimore was not only a thriving center of shipping but also the arrival point for huge numbers of immigrants from Ireland and Germany, giving rise to a deeply entrenched gang culture much like that of New York City. Allegiances were forged according to neighborhood, nationality, and trade, and battles were fought on much the same lines. Gangs with colorful names such as the Rip Raps, Blood Tubs, and Black Snakes ruled the streets, and even reached out to form political alliances. On election days, the gangs took to the streets to intimidate voters and stuff ballot boxes. According to the Baltimore Republican, the “gutters flowed with rivers of blood.”

The violence had intensified during the 1856 presidential election: Eight men were killed in the streets and more than 250 others were injured, reducing a proud community to what one observer called “the Pandemonium of American Cities.” Though Mayor George William Brown had launched a series of reforms by the time of the 1860 election, the city’s bloody reputation persisted. Three decades earlier, President John Quincy Adams had praised Baltimore as the “Monumental City.” At the time of Lincoln’s election, it was known far and wide as “Mobtown.”

The city’s prominence as a rail hub guaranteed that it would feature in the planning for Lincoln’s inauguration, since virtually any route that the president-elect chose between Springfield and Washington would necessarily pass through Baltimore. Few people imagined that Lincoln would receive a cordial reception. In April of the previous year, when the Republican State Convention gathered to elect delegates for the Chicago convention, a group of “local roughs” had stormed the meeting and flipped over the desks and benches. The delegates retreated under a shower of ink pots. “The whole scene was extremely disgraceful,” wrote a correspondent for the New York Times. “For God’s sake let every man and all parties—religious, political or otherwise—when respectful, entertain and express their own sentiments free from molestation.”

The plea went unheeded. After Lincoln’s nomination, his supporters in Baltimore were subject to further violence, as a diehard Republican named Worthington G. Snethen reported to Lincoln himself. “Our people behaved nobly,” said Snethen, recounting an assault on a torchlight procession of Wide Awake marchers. “There were some 300 of them. They walked their whole distance amid showers of eggs, brick-bats and injurious epithets from the mob.” Snethen refused to be discouraged. Following the election, he wrote again, in the hope that Lincoln would reward his “gallant little band” of supporters with a stop in Baltimore on his way to Washington. Snethen promised a courteous reception, but the city’s treatment of President-elect James Buchanan four years earlier suggested otherwise. Traveling from his home in Pennsylvania, Buchanan was said to have received a merciless heckling from Baltimore’s street gangs, with the result that he cut his visit short and departed for Washington on an earlier train.

Four years on, there was little reason to hope that Lincoln would fare better. “The city of Baltimore was, at this time, a slave-holding city,” Pinkerton noted, “and the spirit of Slavery was nowhere else more rampant and ferocious.” Horace Greeley concurred, adding that the city’s rich and powerful were particularly eager to see the Republican agenda derailed. If the Union were dissolved, he explained, Baltimore would emerge as a dominant power in the new South: “In a confederacy composed exclusively of the fifteen Slave States, Baltimore would hold the position that New York enjoys in the Union, being the great ship-building, shipping, importing and commercial emporium, whitening the ocean with her sails, and gemming Maryland with the palaces reared from her ample and ever-expanding profits.” For this reason, Greely concluded, the city’s upper classes were “ready to rush into treason.”

This created an additional problem for Pinkerton. It would not be enough simply to infiltrate the violent gangs at the lower end of Baltimore’s social strata; he would also have to find a find a way of moving among members of the wealthier classes, who would be likely to provide the money needed for any large-scale plot. Accordingly, Pinkerton decided to set up a cover identity for himself as a Southern stockbroker newly arrived in Baltimore. It was a canny choice, as it gave him an excuse to make himself known to the city’s businessmen, whose interests in cotton and other Southern commodities often gave a fair index of their political leanings.

In order to play the part convincingly, Pinkerton hired a suite of offices in a large building at 44 South Street, at the center of the triangle formed by the city’s three train stations. From this vantage point, he could easily gather reports from all quarters and send instructions to his agents in the field. It would not be seen as unusual for a stockbroker to receive frequent visitors, but Pinkerton took care to select a location that would help to shield the identities of his operatives. The building on South Street had entrances on all four sides and could be accessed inconspicuously through an alley at the back. Pinkerton’s agents would be able to assemble in his office without being seen in one another’s company as they passed in and out of the building. If one agent should be compromised, the others would not automatically fall under suspicion. This feature would become especially important as the operation grew in size; Pinkerton’s first order of business on South Street was to wire to Chicago for an additional force of men.

Soon enough, Pinkerton was trading under the name of John H. Hutchinson—which he originally spelled as Hutcheson, Hutchesontown being the name of a district in the Gorbals. By all accounts, he played the role with convincing gusto. To all outward appearances, he was now “an outgoing gentleman of southern birth,” with a resolved but sympathetic demeanor that would encourage people to confide in him. “The detective must always be an actor,” Pinkerton wrote, “and nine-tenths of the actors on the stage today would do well to take lessons in their own profession from him.”

From the office on South Street, Pinkerton assigned new identities to each member of his team. “I distributed my Operatives around the City,” he recalled, after giving each one a distinct set of characteristics “for the purpose of acquiring the confidence of the Secessionists.” Harry Davies, the aristocratic former seminarian, was to assume the character of “an extreme anti-Union man” newly arrived from New Orleans, and put himself up at one of the best hotels in the city. From this platform, Davies was to make himself known as a man willing to pledge his loyalty and his pocketbook to the interests of the South. Kate Warne was to assume the identity of “Mrs. Barley,” passing herself off as a visitor from Montgomery, Alabama—drawing on knowledge gained during the Adams Express robbery case. “Mrs. Warne displayed upon her breast, as did many of the ladies of Baltimore, the black and white cockade,” Pinkerton wrote, “which had been temporarily adopted as the emblem of secession.” Her job was to cultivate the wives and daughters of suspected plotters. “Mrs. Warne was eminently fitted for this task,” Pinkerton noted. “She was a brilliant conversationalist when so disposed, and could be quite vivacious, but she also understood that rarer quality in womankind, the art of being silent.”

Not all of Pinkerton’s agents were comfortable with their assigned roles. One operative, to whom Pinkerton gave the name of Charles Williams, was instructed to pass himself off as a transplant from Mississippi. He promptly hit a snag when he ran across a native of Jackson who appeared determined to engage him in a lengthy discussion of their home state. Fearful of being exposed, Williams excused himself and made his way back to South Street, where he duly recorded the incident in his field report. “I was afraid I could not play my part,” he wrote, but Pinkerton assured him that “there was no danger, and all I wanted was self confidence.” After receiving a few additional pointers, Williams squared his shoulders and returned to work. Pinkerton himself suffered no qualms about playing his role. For the moment, the task at hand appeared relatively straightforward. His goal, as he had described it to Samuel Felton, was to forge a relationship with anyone suspected of belonging to a secessionist group of any kind. The next step would be to “apply the necessary test” by expressing opinions and sympathies designed to tease out any plans for violence. Such methods had worked well in the past, he explained, allowing him “to penetrate into the abodes of crime in all classes of society.”

Even as Pinkerton wrote these words, however, the focus of his operation began to shift beneath his feet. From the first, Pinkerton’s plan of action rested on the assumption that Baltimore’s secessionists intended to attack the railroads as part of a larger plan to capture Washington. Many believed that if Lincoln could be prevented from taking the oath of office in the capital, even if he were to be sworn in at Philadelphia or New York, the Union cause would be lost before the new administration had begun. By keeping Felton’s “road” open, Pinkerton would be doing his part to ensure an orderly inauguration, sending a strong message of Lincoln’s resolve. Even as Pinkerton made his initial report to Felton, however, he caught the first scent of a darker design. On January 27, in Springfield, the president-elect offered up the first details of the itinerary for the forthcoming trip to Washington. Until that moment, the specifics of Lincoln’s journey to the capital had been a subject of furious speculation and debate. Would the newly elected president be able to make a public procession to Washington, as his predecessors had done? Would he be able to set foot in his native Kentucky? Would he even dare to show his face in a slaveholding state? Now, with the date of the inaugural fast approaching, Lincoln announced that he would travel in an “open and public” fashion, with frequent stops along the way to greet the public.

The message was clear: Lincoln was standing firm in the face of the secession crisis. As the Baltimore Sun reported:

It is now positively settled that Mr. Lincoln will depart for Washington on the 11th of February. He will go hence via Lafayette to Indianapolis, where he will receive the hospitalities of the Indiana Legislature; thence he will proceed, probably, by way of Cincinnati to Columbus, Cleveland, Buffalo and Albany. From Albany he intends to make for Harrisburg direct, thence to Baltimore and the Federal Capital; but a tour to New York and Philadelphia is not impossible.

Arrangements for special trains all the way through are making. No military escort will be accepted.

In the days to come, the itinerary would be fleshed out and elaborated upon until every moment of Lincoln’s time was cataloged for the public. By the date of departure, it would be known that Lincoln intended to arrive at Baltimore’s Calvert Street Station at 12:30 on the afternoon of Saturday, February 23, and that he would depart from the Camden Street Station at 3:00. “The distance between the two stations is a little over a mile,” Pinkerton noted darkly. “No provision for his reception had been made by any Public Committee in Baltimore. The few Union men that were there at the time were over-awed by the Secessionists, and dared not make any demonstration.”

Instantly, the announcement of Lincoln’s imminent arrival became the talk of Baltimore. Of all the stops on the president-elect’s itinerary, Baltimore was the only slaveholding city apart from Washington itself, and there was a distinct possibility that Maryland would vote to secede by the time Lincoln’s train reached her border. In that case, what sort of reception might the president-elect expect? The Baltimore Sun expressed a hope that the city would rein in any hostile impulses:

It is of great concern to all who love and would honor the State of Maryland and the city of Baltimore that no demonstration whatsoever should be made, even by a single individual, inconsistent with our self-respect. We would a thousand times rather see the most elaborate exhibition of official courtesy, unbecoming as it would be in such a case, than that the slightest personal disrespect should mar the occasion, or blur the reputation of our well-ordered city.… Let it be the part of every man to sustain the honorable status we profess; and so to illustrate before the eyes of the President elect the self-respect of a people who cordially dissent from his political opinions.

No doubt there were many in the city who shared this noble sentiment. As Pinkerton would soon learn, however, there were some who saw Lincoln’s passage through Baltimore as an open challenge, a red rag trailed before a stirring bull. As of yet, Pinkerton had no idea if the angry talk would resolve itself into a credible threat, or what form that threat might take, but he was now convinced that Baltimore’s secessionists could not be ignored. “Every night as I mingled among them I could hear the most outrageous sentiments enunciated,” he wrote. “No man’s life was safe in the hands of those men.”

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