City on Fire

City on Fire

The night violent anti-government conspirators sowed chaos in the heart of Manhattan.

By Betsy Golden Kellem

The first fire bell rang out at the St. James Hotel at a quarter to nine in the evening. A guest had noticed smoke curling under the door of the room next to his and rushed to the front desk to report it. Upon entering the room, hotel staff found flames spreading across the bedding, which reeked of turpentine. Matchsticks littered the floor alongside a black satchel holding a small glass bottle of liquid. The fire, which was still small, was quickly put out. The man who was staying in the room, who had given his name as John School, was nowhere to be found.

Ten minutes later, a similar discovery was made nearly two miles away at the St. Nicholas Hotel. A bystander claimed to have seen two mysterious men hurrying out of the lobby. Soon after, a fire was discovered on an upper floor of the nearby Lafarge House hotel.

It was November 25, 1864, a clear, cool Friday just after Thanksgiving, and New York City was thick with crowds of people headed out for the night or just enjoying a downtown stroll. The jovial mood shifted sharply as the sounds of alarms erupted in the streets of Manhattan. Frantic guests and staff found rooms aflame at hotel after hotel, including the Metropolitan, the Belmont, Lovejoy’s, Tammany Hall, and the Fifth Avenue. At most of these establishments the particulars were largely the same: sheets, blankets, and furniture piled atop mattresses in a tinder heap; apothecary vials left behind at the scene; guestbook listings indicating that a young man with a generic name had checked into the room.

Disinclined to lose paying customers to the mounting terror outside its walls, the management at Niblo’s Garden, a theater next to the Metropolitan Hotel, sent a young boy onstage with a sign hastily painted with “NO FIRE” in large letters. Nearby, P. T. Barnum’s American Museum wasn’t so lucky. Around 9 p.m., someone broke open a vial of flammable liquid in the museum’s fifth-floor stairwell, and a fire instantly ignited. Thousands of people had gathered for Barnum’s promise of extra performances on Evacuation Day, the anniversary of British troops’ departure from Manhattan after the American Revolution. Among other offerings, Barnum had lined up “three mammoth fat girls,” a collection of French automata, Native tribespeople, and live capybaras and kangaroos. Staff were able to extinguish the flames in the stairwell before any real damage was done. Still, a cry of “Fire!” sent Barnum’s audience running for the exits.

Over at the Winter Garden theater on Broadway, the house was full for a one-night-only performance of Julius Caesar, a benefit intended to raise money to purchase a statue of William Shakespeare to be placed in Central Park. The play’s cast featured the three thespian sons of the legendary Shakespearean actor Junius Brutus Booth: Junius Jr., Edwin, and John Wilkes, on stage together for the first (and only) time. The Great Booth Benefit was the hot ticket of the season; orchestra seats, normally less than a dollar, went for five.

The crowd of 2,000 roared when the brothers made their entrance in the first act. The audience may not have noticed the distant sound of fire-engine bells at the start of act two, but soon enough the din was overwhelming. Someone saw firefighters outside the theater’s windows, near the Lafarge House next door. A man in the dress circle registered his assumption out loud. “The theater is on fire!” he shouted. He was wrong, but it was enough for alarm to spread through the house. Theatergoers abruptly stood, scanning their surroundings for flames and a path to the nearest exit. Edwin Booth stepped to the front of the stage to calm the audience, assuring them in his trademark low tone, “There is no danger.”

The performance resumed, and the New York Herald’s reviewer later dubbed it an example of the “high standard of our public entertainments”—no other theater scene, the reviewer said, could purport to offer “three tragedians, or even one, comparable to any one of the Booths.” Still, a lot more had transpired outside the theater than the audience at the Winter Garden suspected: While the Booth brothers played out Caesar’s untimely end on stage, Confederate arsonists were attempting to burn New York City to the ground.

The next morning’s New York Times reported that the city had been “startled last evening by the loud and simultaneous clanging of fire-bells in every direction, and the alarming report soon spread from street to street that a preconcerted attempt was being made by rebel emissaries … to burn New-York and other Northern cities, in retaliation for the devastation of rebel territory by Union armies.” Coverage suggested that the as yet unidentified arsonists’ plan had been to set fire to various buildings filled with people, divide the authorities’ attention, and then sow further chaos with additional fires, including at the city’s harbor.

The Booth brothers bickered over the news during breakfast the next morning at Edwin’s home in Manhattan. Junius offered that in San Francisco, vigilante groups would have dragged the arsonists into the street and hanged them by now. Abraham Lincoln had only just been reelected for a second term as president, and Edwin, who had cast his ballot for Lincoln, proudly stated that his vote was surely for the Union and an end to the Civil War, now in its fourth terrible year. At this, John Wilkes could not keep silent. His brothers had no idea that, in the weeks leading up to their benefit performance, he had met with Confederate operatives to devise a plan to kidnap the president and hold him hostage. Now John Wilkes spat angrily that Lincoln would make himself king of America, and that the fires were fair retribution for Union general William Tecumseh Sherman’s recent campaign in the Shenandoah Valley.

Edwin goaded his brother, asking, “Why don’t you join the Confederate army?” John replied bitterly, “I promised mother I would keep out of the quarrel, if possible, and I am sorry that I said so.”

At that, Edwin kicked him out of the house.

As with the attack on the U.S. Capitol on January 6, 2021, the lead-up to the arson campaign on November 25, 1864, was long, ugly, and both actively and tacitly encouraged by powerful men.

It is easy to think of Civil War politics dividing neatly along the Mason-Dixon line, and to assume that New York City, jewel of the North, was a Union stronghold immune even to the suggestion of Confederate agitation. This was not the case. The city was turbulent, the site of sometimes violent clashes over issues of class, race, and national allegiance. Some of these events would echo through time: As with the attack on the U.S. Capitol on January 6, 2021, for instance, the lead-up to the arson campaign on November 25, 1864, was long, ugly, and both actively and tacitly encouraged by powerful men.

By the mid-19th century, the Era of Good Feelings was in America’s rearview mirror, and nowhere was this more apparent than in New York. Financial speculation, unstable commodities pricing, and both British and U.S. monetary policies led to the Panic of 1837 and a period of economic depression during which the city saw mass unemployment levels and riots over the price of flour. The elite were too far ahead in white-glove excess to offer any sort of attainable example of prosperity—nor would they wish to—and explosive growth in immigration made it harder for people in New York’s tenements to compete for available jobs. White working-class New Yorkers increasingly felt not only alienated but also motived to express their dissatisfaction.

City politicians manipulated communities and their loyalties to this end. Chief among these individuals was mayor Fernando Wood, described by his own biographer as “almost dictatorial.” Wood was not above using the largely Irish Dead Rabbits gang for his own muscle, even as his political sympathies lay with the anti-immigrant Know-Nothing Party. His municipal police were so corrupt that the state authorities put the city’s law enforcement under their control. Three years later, speaking in Syracuse at a gathering to select New York’s delegates for the Democratic National Convention, Wood boomed with pride that “not one man in this delegation has ever been tainted with free-soil heresies or abolition proclivities,” and that the best course of action was clear: “Let the South alone.” The same year, Wood purchased the New York Daily News (a now defunct paper, not to be confused with the current publication of the same name) and installed his brother Benjamin as its head, assuring himself a friendly mouthpiece throughout the war.

By January 1861, when South Carolina had formally seceded, Wood’s message grew bolder. He recommended that New York secede as well, so that, “as a free city, [it] may shed the only light and hope of a future reconstruction of our once blessed Confederacy.” In language eerily similar to that used by right-wing policy architects in 2024, Wood warned, “We are in the midst of a revolution bloodless as yet.” That November, Wood spoke before constituents at the Volks Garten, a German beer hall on the Bowery. A huge bonfire raged outside the building, clogging the air with thick smoke. Inside, members of the German Democratic Club made sure that the press table was well stocked with frothy mugs of lager and wine by the bottle, and a band played “I Wish I Was in Dixie.” Wood whipped up the crowd with a speech in which he claimed that the Union government had far exceeded its authority, interfering with daily liberties and subsuming citizens under tyranny.

Wood’s bravado was typical of Northern dissenters against the Union. The movement was not especially uniform: Some advocates called themselves Peace Democrats, others Copperheads. Still others considered themselves Sons of Liberty, in the vein of their Revolutionary forebears. They included Southern transplants, states’ rights enthusiasts, businessmen who depended on the South’s cotton crops, and racist opponents of the “Black Republican” party, as they called it. What this wide-ranging bunch shared was deep dissatisfaction over Union policy. They made Lincoln the common target of their rage, and in New York they were powerful: The city twice snubbed Lincoln at the presidential ballot box, even as the rest of the state gave him the votes needed for electoral victory.

In 1863, after two years of war, the federal government instituted a draft for the Union army. Not only was this unappealing to many New Yorkers who opposed the war or supported the Confederacy, but draftees were allowed to pay $300 to avoid service, and much of the public was furious that wealthy residents would be able to buy their way out of the army. There were riots for the better part of a week—“a saturnalia of pillage and violence,” as one paper put it—during which white mobs killed at least 12 Black residents and terrorized thousands more.

Public opinion about the war was also shaped by covert operations. The Union and the Confederacy each engaged in secretive maneuvers, and every time an incident rose to the level of media attention, readers became livid. In March 1864, Colonel Ulric Dahlgren was shot dead in a failed undercover Union attack on Richmond. At first glance Dahlgren, only 21 at the time, may have seemed too young to be leading a secret raid. The leg he had left behind at Gettysburg spoke to greater steel and experience. Papers purportedly found on Dahlgren’s corpse detailed his mission. “The men must keep together and well in hand,” read Dahlgren’s orders, “and once in the city it must be destroyed and Jeff. Davis and Cabinet killed.” Questions soon arose about the papers’ authenticity. Still, the documents stirred outrage among supporters of the Confederacy. Reports that Dahlgren’s body was displayed at the rail station in Richmond in turn incensed Unionists.

By the fall of 1864, when Sherman had taken Atlanta and General Philip Henry Sheridan was running rampant over the Shenandoah Valley, Confederate sympathizers were angrier than ever. If the Union meant to play dirty, they felt, retribution was all but necessary. The Richmond Whig suggested burning Union cities, and claimed that support for the Confederacy was sufficiently strong north of the Mason-Dixon that one need only walk the streets of New York or Philadelphia and offer to pay recruits to assist in the covert task. And if that seemed too risky, there were plenty of “daring men” in Canada who were willing to help.

Robert Cobb Kennedy was one of those men.

Raised in a reasonably well-off Louisiana family, Kennedy entered West Point as a cadet in 1854. (At the time, the superintendent was none other than Robert E. Lee.) Kennedy was a magnet for demerits and a poor student. When grades were posted heading into the cadets’ third year, Kennedy had flunked a fair share of courses. The last straw for West Point administrators was when Kennedy and his best friend, Stephen DeWitt Clinton Beekman, great-grandson of New York’s first governor, decided that if they were headed for dismissal, they might as well go out in grand style. The pair downed a bottle of whiskey and hurled rocks and verbal abuse at the facade of Cozzens’s hotel, situated near campus. Officers dragged the young men away, and they were asked in no uncertain terms not to return to West Point.

Stung by rejection, Kennedy had something to prove by getting involved in the Confederate cause once the war broke out. As soon as he could manage, he enrolled in the First Louisiana Regular Infantry regiment. The First Louisiana was hit hard at the battle of Shiloh and Kennedy was injured, leaving him with a permanent limp. In 1863, he was captured in a Union ambush and spent his 28th birthday in a prison transport headed north.

It was November by the time Kennedy boarded a steam tugboat in Sandusky, Ohio, for the 20-minute ride to Johnson’s Island, a prison camp for Confederate officers located in Lake Erie. The island was spare and unforgiving; a man incarcerated there once commented that “nature had made it an ideal prison.” Escape plans were inevitable but difficult to carry out. The island was a mile from nearest landfall, and a warship patrolled the surrounding waters. Because the prison sat on solid limestone, attempting to tunnel one’s way to freedom was useless. Some escapes failed when a fellow detainee leaked a man’s intentions in exchange for a prisoner swap with the Union or for better perks behind bars.

Still, Kennedy was determined to get out. In the end, he climbed over a prison fence on a moonless night, relying on a fellow detainee to say his name at roll call. After finding a small boat, he made his way to Canada.

The Province of Canada, then a British colony, was officially neutral on the matter of America’s war. Nonetheless, Confederate soldiers and spymasters believed that the territory had much to offer from a tactical standpoint, most of all a thousand-mile border with the Union and thus the possibility of a second front in the war. Men began to gather in secret in Canada and created a satellite secret service for the Confederacy in Toronto. They strategized about seizing ships on the Great Lakes and undertaking guerrilla missions to free imprisoned Confederate soldiers. They even devised an intricate plan to create what they called a Northwest Confederacy. In October 1864, a group of operatives carried out a raid in St. Albans, Vermont, hoping to sow discord and rob banks for the benefit of the Confederate treasury.

At the head of the Confederacy’s Canada contingent was Jacob Thompson, who at one point had been U.S. Secretary of the Interior but resigned in protest a few months before the attack on Fort Sumter in South Carolina. As inspector general of the Confederate army, he supervised covert operations in Canada at the behest of Jefferson Davis himself. Thompson was eager to activate young men who’d found themselves in Canada and were bubbling over with ego, anger, and enthusiasm for the Southern cause—men like Robert Cobb Kennedy. When he came to Thompson’s attention, Kennedy was given a choice: He could try his best to get home to his family and farm, not knowing what condition he’d find them in, or he could become part of this gadfly secret service. “If it is in the service of my country,” Kennedy said, he would stay.

Kennedy agreed to sign on for the latest of Thompson’s plans, which called for small cells of Confederate operatives to travel to New York City, Chicago, and Boston. Once there they would use Election Day 1864 as an opportunity to commit violence, draw in local groups of Confederate supporters, and ultimately seize control of the cities. This was to be a crucial first step toward the formation of a Northern outpost of the Confederacy.

New York was of special interest to the operatives, since it seemed primed for their flavor of discord. The draft riots in 1863 had proven that the city’s population was volatile and that the police could be easily overwhelmed. There were many known Copperheads who might be receptive to Thompson’s plan, and both the mayor’s office and the Daily News seemed well in hand. Indeed, Confederate leaders said that they had been assured of Mayor Wood’s support for the action, noting in a report: “We were told that about 20,000 men were enlisted in New York under a complete organization; that arms had been provided already for the forces in the city, and we would be expected to take military supervision of the forces at the vital moment.”

In other words, operatives expected that, after they set fires across Manhattan, Copperheads in solidarity with their efforts would seize the chaotic moment to take over the city’s federal infrastructure and free Confederate prisoners from nearby Fort Lafayette. As for Major General John Adams Dix, a sometime rail baron, postmaster, and politician who commanded the Union army’s Department of the East, based in New York, the operatives hoped to toss him into the tiniest, clammiest cell they could find.

Secrecy was of the essence; only a few men in Toronto knew about the plan. In addition to Kennedy, who was fresh out of prison, there was Confederate colonel Robert M. Martin of Kentucky, the designated leader of the group, and lieutenant John Headley; John Ashbrook, James Harrington, and James Chenault of Kentucky; and John Price of Virginia. (An additional conspirator’s name has been lost to time.) The men traveled in pairs to avoid suspicion, arriving in New York about two weeks before the election to get the lay of the land. Headley bore a letter of introduction to their principal contact, James McMaster, a states’ rights enthusiast and editor of the Catholic Freeman’s Journal. McMaster believed that the Lincoln administration wanted to “turn loose upon the country a horde of negroes utterly unfit for liberty.” He went so far in his criticism of the federal government at the outset of the Civil War that he was arrested and briefly imprisoned for producing a seditious paper.

The conspirators arrived from Canada and registered under false names at hotels and boarding houses around New York. Occasionally, they changed locations to avoid anyone becoming too familiar with their faces or routines. Kennedy went to the Belmont Hotel with papers identifying him as a college boy “spending his vacation in the city.” After three days, he moved on to a boarding house on Prince Street owned by a woman named Lydia Oatman.

Martin and Headley met with McMaster for a Sunday dinner to plan the operation in more detail. “It was determined that a number of fires should be started in different parts of the city,” Headley later recalled, “which would bring the population to the streets and prevent any sort of resistance to our movement.” McMaster told the men that he had privately arranged for a supply of so-called “Greek fire” to be made. Though the name originated with a flammable compound used in the Byzantine world, by the 19th century Greek fire was a catch-all term for any volatile incendiary material that burst into flames when exposed to air.

Choosing fire was a signal that the men intended to cause both fear and ruin. Tinderbox construction, unregulated industry, and building density in New York meant that fire, once sparked, tended to spread fast. Residents still shuddered at the memory of the city’s worst conflagrations. In September 1776, while New York was under British occupation, a blaze took down more than a fifth of the city; each side of the Revolutionary War blamed the other for starting it. The great fire of 1835 occurred on a night so cold that the East River froze over. As firefighters tried in vain to draw water, flames burned 50 acres of Manhattan in 24 hours, resulting in the equivalent of half a billion dollars in damage. Ten years later, a fire inside a whale-oil factory spread to other buildings and caused a massive warehouse of saltpeter to explode.

Support for the operation was as important as the method of destruction. McMaster claimed that in addition to gaining the mayor’s support, he had secured a meeting with New York governor Horatio Seymour’s private secretary, whom he was certain would extend “the support of the governor’s official neutrality.” (It was well-known that Seymour loathed Major General Dix, and he was on record criticizing Lincoln’s leadership as “ignoble tyranny which now degrades the American people.”) After the insurrection, McMaster was sure that friendly representatives from neighboring states would meet in New York to formulate a political strategy for cementing the power of the Confederacy in the North.

In the meantime, it was decided that the operatives would use a wholesale piano store as a storage site for their supplies. It was owned by Augustus McDonald, a brother of Confederate explosives expert Lawrence McDonald. The conspirators’ trunks were hauled from the train depot to the store for safekeeping. In the run-up to the Election Day strike, some of the men decided to enjoy themselves. They visited theaters, took in pre-election debates at Tammany Hall, and watched as a massive torchlight procession made its way down Broadway under the review of General George McClellan.

Kennedy didn’t join them. He worried that his limp would make him identifiable, and that former friends and West Point classmates in the city might recognize him. Besides, he had embarked on something of a fling with Lydia Oatman’s chambermaid.

Confederates wreaking havoc on New York in the midst of Thanksgiving festivities could still devastate the city and humiliate the president.

When the conspirators read the papers on November 3, they learned of a potential complication to their plans. The Union government was apparently aware of the threat they posed: A telegram from Secretary of State William Seward had alerted municipal leaders that “there is a conspiracy on foot to set fire to the principal cities in the Northern States on the day of the Presidential election.” The conspirators’ alarm grew the following day when they heard rumors that Union general Benjamin Butler, whose stern command of New Orleans had earned him the nickname the Beast, was on his way north and would temporarily assume Dix’s role in New York.

By November 5, Butler had indeed assumed command at the Union army’s New York headquarters, and he intended to keep the peace with the 3,500 troops he had at his disposal. On November 7, the day before the election, the front page of the New York Times read:

TO-MORROW’S ELECTION

Gen. Butler in Command in the State of New-York

GENERAL ORDERS NO. 1

Troops Detailed to Preserve the Peace and Prevent Rebel Incursions

NO INTERFERENCE WITH THE ELECTIONS

Raiders and Rebels and Ballot-box Stuffers Warned

Butler’s arrival caused shock and anger among Confederate leaders in Toronto, and some paranoia, too. Thompson and others worried that someone on the inside had let their plans slip. If so the operatives might be in danger of arrest or worse. Thompson and his colleagues sent word to McMaster in New York on the eve of the election that they should postpone the action. McMaster followed orders, directing the operatives to stand down.

On Election Day, Lincoln won a second term. Governor Seymour was voted out of office. And in Chicago, the papers reported that several Confederate operatives who had been assigned by their superiors in Canada to carry out that city’s takeover effort had been arrested. (Covert action in Boston never materialized.)

It seemed as if the moment for a coordinated insurrection had passed. Nonetheless, members of the New York crew were champing at the bit. They had come to the city to take action, and they were determined to do so. The men decided that the upcoming Thanksgiving weekend was a good time to carry out a revised plan. The Lincoln administration had made Thanksgiving a national holiday only the year before, with the express intention of celebrating, among other “blessings,” the fact that “the theatre of military conflict … has been greatly contracted by the advancing armies and navies of the Union.” Perhaps they couldn’t seize the city, but Confederates wreaking havoc on New York in the midst of Thanksgiving festivities could still devastate the city and humiliate the president.

The operatives insisted that they could regroup and complete their new mission, and the Confederate leadership in Canada appeared supportive. But the men’s local contacts resisted. McMaster withdrew from having any direct connection with the operation, and the gentleman who was supposed to oversee procurement of the Greek fire, one Captain Longmire, threw up his hands and left town, renting a cottage in the country where he planned to remain until things blew over.

Still, Longmire gave Headley a street address and told him that the Greek fire had already been paid for, should he wish to pick it up. If they chose to, the men could act on their own.

The conspirators agreed to set fires in various hotels, hoping to cripple the city’s business district, which was centered on Broadway. The plot had two phases. In the first, the men would check in to hotels across the city, carrying cheap black satchels with long overcoats rolled up inside. They would give a false name at the front desk, then make their room appear occupied before donning the overcoat and exiting the premises quietly, leaving the empty satchel behind. Each man would do this at three or four hotels. The second phase would begin a few days later, around 8 p.m. on November 25. The men would return to the hotels, this time with Greek fire and turpentine. They would set the room aflame and then leave.

Headley was tasked with procuring the Greek fire. He knocked on the door of a house in Washington Place on Thanksgiving Day, and was met in the basement by an old man with a thick beard. Headley told the man that he was there for Captain Longmire’s valise. The man said nothing in return but handed Headley a leather bag, about two feet long and heavier than it looked. Headley tried not to draw attention to himself as he left the house and boarded a streetcar uptown, but the chemicals in the bag reeked of rotten eggs. Passengers reseated themselves farther down the car and shot him nasty looks. One man said as he got off at his stop, “There must be something dead in that valise.”

Headley met with the other conspirators in a cottage near Central Park to strategize. His valise held 12 dozen glass bottles, weighing four ounces each and sealed with plaster of Paris. Inside the bottles was a clear liquid that looked like water—in fact, it was white phosphorus, a highly flammable substance, dissolved in carbon disulfide. The men considered the clinking glass vials and agreed, as Headley later put it, that they were “now ready to create a sensation in New York.”

Before embarking on the mission, the men looked at one another across the table in the cottage. Kennedy said that from there on out, it was all or nothing. In an era when cutlery was sometimes carved from rams’ horns, a saying had emerged to describe those occasions when an effort was sure to be either a great success or a terrible failure. Kennedy used it now: “We’ll make a spoon or spoil a horn.”

Upon completion of phase one, most of the men reconvened at the cottage early in the evening of November 25. Two conspirators were no-shows. Those who gathered slapped one another on the back for encouragement and filled their pockets with vials of Greek fire wrapped in plain paper. They resolved to meet back at the cottage the next day to debrief. Just after 7 p.m., they walked into the bustling fall night.

Headley arrived at the Astor House hotel about 20 minutes later, asked for the key at the front desk, and went upstairs to his room. Locking the door behind him, he turned around and lit the room’s gas jet. He took a moment to enjoy the view of Broadway from the window and then got to work. After stripping the bed with a yank, Headley piled the sheets against the headboard, then stacked chairs, dresser drawers, and anything else made of wood onto the mattress. He added newspapers to the pile, produced a bottle of turpentine, and shook its contents over the heap.

Headley unlocked the door in case he had to get out in a hurry, then opened the vial of Greek fire and poured it onto the bed. Flames leapt to life, accelerated by the turpentine. Headley stepped into the hall, closed and locked the door, then walked briskly to the front desk, where he left the key before exiting into the street.

Kennedy and the other men did the same at more than a dozen hotels around Manhattan. When Headley finished with his hotels, he turned his attention to the city’s waterfront. Barges bobbed in the harbor barely 20 yards from the street, close enough for a man with a good arm to hurl bottles of Greek fire onto the vessels’ decks one by one. The Merchant, a barge near Franklin Street, was loaded with 2,000 bales of hay and made a particularly seductive target. The hay burned fast and bright, sending reflections rippling across the surface of the Hudson River.

Before long fire bells were ringing across the city. Around 9:15 p.m., Headley “concluded to go and see how my fires were doing.” There was no panic at the Astor House hotel, oddly, but he saw crowds pouring out of Barnum’s American Museum at the intersection of Broadway and Ann Street nearby.

Headley learned what had happened when he came across Kennedy near City Hall a little while later. Kennedy said that he had set fires at his assigned hotels as planned, then figured he’d enjoy himself until all hell broke loose. He had a few drinks and strolled to Barnum’s Museum, where he gazed up at the looming white facade with its paintings and banners, then put down 30 cents and went inside. After roaming the galleries for a few minutes, an inebriated Kennedy noted that the fifth-floor stairway was clear of people and decided it “would be fun to start a scare.” Drawing a leftover bottle of Greek fire from his pocket, he broke it open on the edge of one of the stair treads as if it were an egg. As flames spread, he watched the ensuing terror among museumgoers with amusement.

The Confederate operatives were high on adrenaline and satisfaction, but this was quickly replaced by the wobbly feeling that they’d been had. Sure, the city was in a bit of a panic, but it seemed as if all the fires had been discovered promptly and put out. Barnum later wrote in a letter to the New York Times that his museum hadn’t been damaged in the slightest. “So speedy was the extinguishment of the flames arising from the liquid ignited on the stairs,” the letter read, “that not even a scorch is visible.”

Where was the uncontrollable inferno? Headley theorized that Longmire and the chemist who’d made the Greek fire had conspired to thwart their plans. In fact the failure was simpler: The men didn’t understand that fire required good airflow to reach its destructive potential. Had they opened the windows of the rooms they set ablaze, the hotels and adjoining buildings may have been reduced to ashes. New York had been saved by insufficient ventilation.

The men—exhausted, and in Kennedy’s case still drunk—found lodgings at a hotel around 2 a.m. and retired for the night. The next morning, Kennedy was sitting in the lobby with his colleague Robert Martin, reading the papers, when a familiar figure entered. Kennedy went white when he realized that it was the city’s chief of detectives, John Young. The chief chatted with the front desk attendants, advising them to add extra watchmen while the investigation into the fires was ongoing. He then plopped down in a chair right next to Martin. The thought occurred to Kennedy that he might be detained or, worse, killed right then and there. He was relieved when a patrolman called from outside, prompting Young to get up and leave the lobby.

Kennedy was not keen to leave the hotel, but Martin was hungry enough to meet Headley for a late breakfast at Broadway and 12th Street. The place was crowded and everyone was murmuring with shock about the prior evening’s events. The men ordered food and grabbed a selection of newspapers, which had already reported that “rebels were at the head of the incendiary work.” By that afternoon, editors were beginning to print a list of every false name the men gave at the hotels, where staff had been all too willing to describe the pseudonymous guests to reporters.

The arsonists decided that it was time to get the hell out of New York. That evening they reconvened at the cottage, relieved to discover that none among their ranks had been arrested. They decided to leave town on a train departing the city at 11 p.m. They bought tickets for a sleeper car, which began boarding at nine, and when the hour arrived the men slipped into their car together. Unwilling to let down their guard until the train left the depot, the men looked out the windows for signs of police. Finally, the steam whistle blew and the engine lurched forward.

Kennedy and his cohort arrived in Albany just before dawn and spent the day in their hotel rooms, since connecting trains wouldn’t be departing until later in the evening. That night they rode in a sleeper car to Canada, arriving in Toronto in the next afternoon. Their work had not gone as planned, but crossing into Canadian territory had surely been a relief. The feeling would be short-lived.

Unknown to the arsonists, New York police had been aware of their conspiracy for weeks. An anonymous informant in Canada had provided information about the original Election Day plot, and requested a hefty reward in return. The Union government was not about to pull out its checkbook without clear proof, but it was willing to pay up if a cursory investigation revealed that the story was true. So detectives had tailed Kennedy, Martin, Headley, and their collaborators upon arrival in New York. But as Election Day came and went, and their activities failed to align with the intelligence tip, the police disregarded them as a threat.

After the attacks, the police made a handful of arrests of suspicious individuals, including a woman from Baltimore who had been seen at the Metropolitan and another hotel the night of the fires (a coincidence, she claimed). The suspects had no relevant information to share and were soon released. A note found at the Astor House then pointed police in the right direction; it was written on stationery from McDonald’s piano store and loosely described a Thanksgiving-night meeting. The store was put under surveillance.

On November 29, at a meeting chaired by William “Boss” Tweed, the city’s board of supervisors unanimously voted to authorize a $5,000 reward for the capture of the arsonists, and further resolved that the police could use their discretion in tapping municipal funds “to procure the arrest and conviction of criminals and others endangering the safety of the community.” Major General Dix, who by then had resumed his role as commander of the Union army’s Department of the East, was determined to do his part to root out the suspects. Though in his mid-sixties and too old for combat, Dix would let no one mistake his wavy white hair and grandfatherly bearing for weakness. By November 27, he had issued General Orders assuring the public that “all such persons engaged in secret acts of hostility here can only be regarded as spies, subject to martial law, and to the penalty of death…. If convicted, they will be executed without the delay of a single day.” All residents of the “insurgent States” present in New York City were commanded to report and register themselves with Dix’s department or be treated as a spy. Dix would have attempted a Union invasion of Canada, too, had the War Department in Washington not in a panic persuaded him otherwise.

The police superintendent at the time was John Alexander Kennedy, a Tammany Hall member and the son of Irish immigrants. (He was not a known relative of the Confederate operative with the same last name.) Kennedy was a reform-minded Republican who had been beaten bloody in the 1863 Draft Riots, and he was eager to get to the bottom of the arson plot. Anonymous letters flooded into his office with theories and misinformation—it was hard to tell the two apart—and the local papers engaged in all manner of speculation. When the initial arrests didn’t pan out, and Dix’s registration line for Southern residents proffered no leads, Kennedy concluded that the men responsible must have fled north to Canada. He immediately sent a trio of detectives to Toronto, including Chief Young, who had all but brushed shoulders with the conspirators in the Manhattan hotel lobby. Based on investigation intelligence and the earlier Election Day plot tip, the detectives set out to learn anything they could about the men’s whereabouts and activities.

On a snowy night shortly after the conspirators had returned to Toronto, Colonel Thompson, the Confederate spymaster north of the border, contacted Headley to alert him that several detectives from New York had also arrived in the city. One of them had asked for the conspirators by name at the Queen’s Hotel, where Confederates were known to stay. Thompson advised Headley and his comrades to keep a low profile.

But the detectives were doing more than asking around—they were also actively working to infiltrate the Confederate organization in Toronto. It was not a terribly difficult task: Young and the other detectives only had to spout the right talking points over a drink or two to be welcomed into the fold. Presenting themselves as “bitter Secessionists,” according to the New York Times, the detectives “made it convenient to curse ‘Beast Butler,’ ” who had guarded New York through the election, and “styled the President the great Illinois ape.”

Young gained the confidence of Larry McDonald, whose brother owned the piano store in New York, and got him to spill the whole boastful story of the arson plot. McDonald also mentioned that two of the conspirators, one of whom was Kennedy, were at that very moment planning to leave Canada and return to the South. They considered trying to run marine blockades down the East Coast, but decided it would be safer to obtain train passage to Kentucky, the gateway of the Confederacy.

Arresting the arson suspects in Canada was a dicey prospect, given that the territory’s government would have to agree to extradite them to the U.S. to stand trial. Now McDonald’s information presented the detectives with a grand opportunity: As soon as the conspirators set foot on American soil, they were fair game for law enforcement. So the detectives left Toronto, crossed the border to Michigan, and waited for inbound trains to arrive.

In closing Kennedy warned, “Burn this. Stationery is dangerous.”

After saying farewell to their friends in Toronto, Kennedy and his co-conspirator John Ashbrook boarded a train on the Grand Trunk Railroad line bound for St. Clair, Michigan. Kennedy was dressed in a plain gray suit and dark overcoat with a Confederate $20 bill sewn into the lining. His papers identified him as Richard Cobb of Illinois. On December 29, Ashbrook and Kennedy trudged through bitter cold and thick snow to catch a connecting train in St. Clair, this one bound for Detroit. The train was crowded. Kennedy swung into the first open spot he could find, and Ashbrook continued on to a window seat at the rear of the car.

Accounts differ as to what happened next. Despite not being present at the scene, Headley later claimed that detectives boarded the train and made their way straight to Kennedy. When Ashbrook saw what was happening, and that he’d be unable either to help his friend or to exit safely through the train’s doors, he threw open the window by his seat, allowing a rush of cold air into the car. He threw one leg out the window, pulled his body through, then leapt from the moving train, rolling into a snowbank.

Detective James Bennett told a different story: He said that Kennedy had been arrested, by himself and his colleagues, outside the train depot in Detroit. Bennett reported that he and his partner, Christian McDougal, sidled up to Kennedy in the chilly street and asked him for identification. McDougal examined the papers, looked Kennedy in the eye, and said, “Your name is Stanton”—the alias Kennedy had used in New York. Kennedy reached for a gun, but before he could grab it the detectives had his arms pinned to his body.

Either way the story ends the same way: Ashbrook escaped and eventually made it to Kentucky; Kennedy ended up back in New York City, where he was held for processing and interrogation at police headquarters at 300 Mulberry St. The holding cell’s turnkey, Edward Hays, struck up a conversation with Kennedy and mentioned that a prisoner had once offered him $1,500 in gold for a chance to escape. Kennedy wasn’t sure he could trust Hays, but he knew that he needed to flee—if convicted, he faced a death sentence. So he told Hays that he knew where to rustle up some cash. Could he have a pen and paper?

On January 11, 1865, Kennedy wrote two letters. The first was addressed to Hiram Cranston, the keeper of the New York Hotel and a man with known Southern sympathies. Kennedy did not know Cranston personally, but he was aware of his reputation and means. Introducing himself as “a Capt. in C.S.A.,” Kennedy asked if Cranston might raise $1,500 in gold for his release. Kennedy assured Cranston that if he and his father couldn’t repay the amount in cotton, “the C.S. Agent in Canada, Hon. J. Thompson, I know would cheerfully refund the amount.” His second letter was to Benjamin Wood, Mayor Wood’s brother and owner of the Copperhead-friendly Daily News. Kennedy again asked for funds, pleading, “If I could only see you I am satisfied I could convince you of my ability to make it ‘all right.’ ”

Hays left, letters in hand, and later returned to the damp cells on Mulberry Street to inform Kennedy that neither Wood nor Cranston was willing to give him any money. Kennedy then resorted to more personal—and riskier—tactics. On January 15, he dispatched Hays with a letter he had written to McMaster. Pretending to be a stranger lest he implicate McMaster in the arson plot, Kennedy wrote:

My Turnkey the bearer of this, I have bribed to release me if I can get some responsible man in the City to be my security, or guarantees that the money will be forthcoming— He says if he can get such guarantee for five hundred dollars he will get me out tonight. I have not time to explain matters or make suitable apologies for thus addressing you—an entire stranger— Question him as regards my condition. Do not promise him any money in advance for I believe him to be a scoundrel—any arrangement you may make to effect my release will entitle you to my eternal gratitude. I can refund any sum under $1500 as soon as I reach Canada.

In closing he warned, “Burn this. Stationery is dangerous.”

Two days later, Kennedy was still locked up at Mulberry Street. He had privately admitted to Hays that he set fires in the lower part of the city, but he wouldn’t name the hotels he targeted. Dix, eager to see the case move forward, issued orders appointing a military commission to conduct Kennedy’s trial. Convinced of the increasing gravity of his situation, Kennedy scribbled a second letter to McMaster, begging for his assistance. “I submit this business to you,” Kennedy wrote, “if you can aid me without injuring yourself I ask you to do it but if you have to place yourself in the hands of any son of a bitch why? refuse altogether + leave me to my fate.” He signed the letter with a desperate postscript, daring to put his pseudonym to paper: “You remember Stanton do you not?”

The letter had only just left Mulberry Street when army officials entered Kennedy’s cell, accompanied by Major John Augustus Bolles, the judge advocate assigned to prosecute him. They informed Kennedy that he would be tried as a spy, that he was entitled to counsel, and that he could enter a statement into evidence with the hope of persuading the military commission to offer mercy. Kennedy gave a mundane summary of his time in New York, claiming that he had visited the city to “spend a few weeks, have some fun, & run the blockade to Wilmington.” He added, “I decline to state whether I had any errand in N.Y. other than I have stated.”

Proceedings against Kennedy began on January 31. Kennedy entered a plea of not guilty, but he had been correct when he noted that “stationery is dangerous.” At the trial, Hays appeared as a witness for the prosecution. It turned out that he was a tool of the police department. Offering a seemingly friendly ear, Hays would talk to prisoners, offer to carry their letters, and then show the correspondence to his superiors. Kennedy’s letter to Cranston, on review, had been “deemed advisable not to send.”

As for the other letters, police superintendent Kennedy testified that he and Dix had reviewed them, made copies for themselves, and allowed Hays to take them to their intended recipients. The copies were entered into evidence, and Hays confirmed that in his conversations with Wood and McMaster, the men had been unwilling to jeopardize their standings or fortunes for a foot soldier in a misdirected plot. Hays testified that Wood had opened the letter and huffed that he did not recognize any such business. Turning his head away, he tore the letter in half.

McMaster got to say his piece in person, when he was called as a trial witness. He claimed not to know Kennedy. As for the arson scheme, he said that no military officer he knew would have done such a harebrained thing. “It was rather the work of some half-crazy women or noncombatants,” he argued.

After several days of testimony and the submission of evidence, the commission came to its decision on February 27: Kennedy was found guilty and sentenced to death.

If the New York arson plot seems especially resonant with recent events, it’s in part because swaths of the American people and some of the country’s most powerful institutions have failed to reckon with the nation’s history of right-wing violence. There is a tendency to close the book on past horrors, rather than consider their causes and grapple with their impact. The result is a sanitization of U.S. history, in which we’re taught to forgive or rationalize the sins of violent white men, if we’re taught about them at all.

Most everyone involved with the conspiracy to burn New York moved on with their lives in peace. John Headley was pardoned for his Confederate service shortly after the Civil War by President Andrew Johnson; he became secretary of state in Kentucky, and in 1906 published a full-length memoir, entitled Confederate Operations in Canada and New York, that described the arson conspiracy. Robert Martin was also pardoned, and later worked in the tobacco industry. John Ashbrook became an insurance agent. James McMaster died in 1886, and a lengthy New York Times obituary praised him as a “commanding figure” and theologian, barely mentioning that he had once been jailed for sedition.

No doubt the arsonists hoped that they would be remembered as bold heroes, and for a time, in some circles, they were. They benefited from the Lost Cause myth, according to which the South fought to preserve states’ rights and liberty rather than the institution of slavery, and the Confederacy was a land of heroism and honor. This mythology would hold strong for decades, and not just in the South. Only after the murder of George Floyd in 2020, and months of subsequent protest and dialogue about systemic racism in America, did the federal government arrive at the decision to remove Confederate generals’ names from U.S. military bases—more than 150 years after the end of the Civil War. Today, many right-wing politicians still spout Lost Cause rhetoric and advocate a vision of America rooted in white supremacy and Christian Nationalism.

In the end, Robert Cobb Kennedy was the only man brought to account for the arson plot. He was imprisoned at Fort Lafayette, on a small island in the Narrows between Brooklyn and Staten Island, and scheduled to be hanged on March 25, 1865. Up until that day, according to press accounts, Kennedy was energetic in his bearing. He would go from cursing his foes from the fort’s damp casements to bargaining for reprieve; from getting drunk on whiskey smuggled in by his lawyer to chatting casually with the prison chaplain. He swore that the Union would never dare provoke Southern retaliation by hanging him, and repeatedly attempted to escape the island fortress. (The prison’s commander caught him trying to jimmy a lock with a red-hot poker.) But after an appeal to President Lincoln himself failed, Kennedy finally agreed to sign a confession for his crimes. At the very least he wanted to tell his side of the story.

Lieutenant Colonel Martin Burke visited Kennedy’s cell the night before his execution to secure his testimony. Kennedy acknowledged his role in the plot with alarming lightness, calling it “a huge joke on the fire department.” Of Barnum’s Museum, he said it “was set on fire by merest accident, after I had been drinking, and just for the fun of a scare.” Turning serious for a moment, he said to Burke, “We wanted to let the people of the North understand that there are two sides to this war, and that they can’t be rolling in wealth and comfort while we at the South are bearing all the hardships and privations.” He also claimed that “we desired to destroy property, not the lives of women and children,” before shrugging and admitting, “that would of course have followed.”

On the day of his execution, Kennedy ate a hearty breakfast and packaged up photographs of himself with locks of his hair, to be sent to family and friends as mementos. He then proceeded to the gallows. The appointed executioner was a Union army deserter whose offense was pardoned in exchange for his new line of work. An officer read a summary of the charges, and Kennedy spat in response to each that it was “a damned lie.” Just before Kennedy dropped to his death, making him the last Confederate soldier executed by the Union during the Civil War, he shouted the words of an old ballad:

Trust to luck, trust to luck,

Stare fate in the face,

Sure your heart will be easy

If it’s in the right place.

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