Disunion follows the Civil War as it unfolded.

In the waning days of the Civil War, as a Northern victory became both obvious and inevitable, the Confederate government of President Jefferson Davis financed what it hoped would be a drawn-out war of attrition, with the intention of driving President Abraham Lincoln to the bargaining table. A large part of that strategy involved members of the South’s Secret Services, who hatched a series of plots against Union territory that featured Canada as their operations site and relied on an impressive network of hundreds of soldiers, agents and operatives. Their most ambitious plot? To burn New York City.

The South hoped to foment an uprising of disenchanted Northerners: Copperheads, the rabidly anti-Republican Order of American Knights and its subset, the Sons of Liberty. To this end, the Davis government sent weapons and money to ensure support in several of the North’s major cities. The plan was for this alliance to first make itself known in Chicago and New York City in early November 1864 – on Election Day. With the promised support of New York’s Democratic governor, Horatio Seymour; the former New York City mayor Fernando Wood; and the Illinois Democratic Congressman James C. Robinson, squads of handpicked Rebel operatives traveled from Canada to New York and Chicago, to rally their supporters.

According to the plan, several small fires were to be set, to distract the authorities while the Rebels and their Northern sympathizers seized each city’s treasury and arsenal and liberated Confederate prisoners of war – from Fort Lafayette in New York, and camps Chase and Douglas in Illinois.

Eight Rebels, all veterans, had been assigned to New York under the command of Col. Robert Martin, a hard-core combat officer. As Martin saw it, “The way to bring the North to its senses [is] to burn Northern cities.” Although the original plan had called for several small distraction fires, Martin planned to burn Gotham to the ground, and he determined to wait out federal troops under the command of Gen. Benjamin Butler. John W. Headley, a member of the team, later wrote that they were resolved in “our purpose to set the city on fire… and let the Government at Washington understand that burning homes in the South might find a counterpart in the North.”

The Rebels had secretly contracted a retired druggist to make 12 dozen four-ounce bottles of the volatile incendiary substance known as Greek fire. Headley later recalled that with their 144 bottles, “we were now ready to create a sensation in New York.” They planned to set fires in the various hotels, “so as to do the greatest damage in the business district on Broadway.” According to Headley, they agreed to begin the operation at 8 p.m., to give the hotel guests the opportunity to escape, “as we did not want to destroy any lives.”

But when the time came to actually bear arms, few stepped up. And, as had happened in earlier plots, word of the planned revolts leaked, all the way to Washington. Secretary of State William H. Seward sent a telegram to New York City’s mayor on Nov. 2, advising him of “a conspiracy on foot to set fire to the principal cities in the Northern States on the Day of the Presidential election.”

Shortly thereafter, thousands of federal troops marched into New York with General Butler, who established a perimeter around the city. The troops were supported by gunboats stationed at various points on the rivers surrounding Manhattan. Meanwhile, in Chicago, a former Confederate spy informed on the agents positioned there, and most of the ringleaders were captured. Ancillary plans for fires and rallies in Boston and Cincinnati were betrayed and abandoned as well. By Nov. 15, General Butler reasoned that New York was secure from sabotage, and marched his troops out of the city.

The New York raiders weren’t done, though. They got back together, and agreed to attempt their strike again in another 10 days, by which time two of their number had lost heart and deserted. The remaining plotters would each be responsible for burning four hotels. Each man was to place 10 bottles of Greek fire, wrapped in paper, in his coat pockets. At the appointed time, they would go from hotel to hotel, firing the rooms and escaping before the alarm sounded. They would meet again the next evening, and make their way back to Canada.

The scheme was a sound one. As The New York Times later observed, “The plan was excellently well conceived, and evidently prepared with great care, and had it been executed with one-half of the ability with which it had been drawn up, no human power could have saved this city from destruction.”

On Nov. 25, James Headley began his part of the operation in his room at the famous Astor House. He later described the event in great detail, illustrating how he “hung the bedclothes loosely on the headboard and piled the chairs, drawers of the bureau and washstand on the bed.” He covered everything with newspaper, doused it in turpentine and emptied a bottle of Greek fire on the pile. Immediately, the bed was aflame. Headley rushed out of the room, locking the door behind him. He followed the same method at the City Hotel, the Everett House and the United States Hotel. Looking back at the Astor House, Headley could see flames in the window of his room. By this time fire bells were sounding all over the city, “great crowds were gathering on the street, and there was general consternation.”

To Headley’s surprise, a fire had also been set in Barnum’s Museum, across the street from the Astor House. Apparently, Capt. Robert Cobb Kennedy had strayed from the plan. Kennedy, it seems, was a drinking man, and after firing rooms in three hotels, he paused for a libation in a local saloon. Inspired by drink, he wandered into Barnum’s, threw down a bottle of his Greek fire, and exited as the stairway became engulfed in flames. Panic ensued. There were 2,500 people in the museum, attending a play in its lecture hall. Miraculously, no one was killed.

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The raiders had set fires in enough hotels to keep the alarm bells ringing and the firemen busy for hours. Pandemonium ruled in the streets – but the young plotters had made a crucial mistake. None realized that the incendiary liquid required oxygen to spread, and in their ignorance, they had closed the doors and windows of the various rooms in which they set their fires. The lack of oxygen made the fires easy to contain and extinguish; some merely went out on their own. In the open spaces where the liquid was thrown, such as Barnum’s Museum, the fires had a greater opportunity to spread. Over all, however, the plot resulted in costly but limited property damage, no loss of life, and a city that was singed but certainly still standing.

The next morning, all of New York City’s newspapers ran front-page accounts of the raid, as well as physical descriptions of the raiders, the fictitious names they had used to register and the promise that they would all be in custody by the end of the day. Gen. John A. Dix, commander of the New York-based Eastern District, made it clear that any conspirators he caught would be tried by military court and hanged within hours. Incredibly, despite the intense manhunt being conducted throughout the city, Martin and his party were able to purchase tickets the next day and board a train for Albany, and from there to Toronto. All the saboteurs made it safely across the border.

Two days later, several New York detectives arrived in Toronto. With the attack on New York, Canada had ceased to be a bastion of certain safety, and some of the Rebels made immediate preparations to return home. All made it but one. Robert Cobb Kennedy was arrested by two detectives at a railway station outside Detroit. Kennedy was tried and convicted in New York, and on March 25, 1865 – just weeks before the cessation of hostilities – he was hanged at Fort Lafayette, in New York Harbor (built on an artificial island, Fort Lafayette was later demolished to make way for the Verrazano-Narrows Bridge). Kennedy was the last soldier of the Civil War to be executed. Before the hood was placed over his face, Kennedy tremulously sang an old Irish drinking song ironically titled, “Trust in Luck.”

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Reactions to the raid were universally harsh. All the Northern papers, including the Copperhead organs, condemned it. The Confederate government at Richmond disavowed any involvement. Even The Richmond Whig, which had once called for the burning of the city, now protested, “If there is any place in the North that ought to be spared, that place is New York.”

The failure of the raid, along with the widely negative response it engendered, all but ended the possibility of future operations out of Canada. Indeed, the entire Confederate secret war had proved an almost total disaster, doomed by inexperience, naïveté, bad luck and betrayal. As John Headley later recalled, “There appeared nothing to do now, since all our attempts everywhere had failed.” For the Confederacy, the end was scant months away.

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Sources: Nat Brandt, “The Man Who Tried to Burn New York”; James W. Headley, “Confederate Operations in Canada and New York”; James D. Horan, “Confederate Agent”; Robert R. Mackey, “The Uncivil War”; Jane Singer, “The Confederate Dirty War”; Mason Philip Smith, “Confederates Downeast”; William A. Tidwell, “Come Retribution.”

Ron Soodalter is the author of “Hanging Captain Gordon: The Life and Trial of an American Slave Trader” and a co-author of “The Slave Next Door: Human Trafficking and Slavery in America Today.” He is a frequent contributor to America’s Civil War magazine, and has written several features for Civil War Times and Military History.