The Failed Confederate Plot to Burn New York City

November 25, 1864 (Friday)

Though news of Sherman’s swath being cut through Georgia had not filtered too far beyond the state, Philip Sheridan’s gutting of the Shenandoah Valley was as terrifying as it was loathed. Most in the South could do nothing, save fume and rant. A few, however, plotted their retaliation.

Jacob Thompson
Jacob Thompson

It all started in October, when Jacob Thompson, former United States Secretary of the Interior (under Buchanan) devised a plan to set New York City ablaze. President Jefferson Davis had sent Thompson to Canada earlier in the year as a sort of head of the Confederate Secret Service. It was he who tried to orchestrate plots to free the prisoners on Johnson’s Island. Thompson was a veritable fountain of failed plots.

Still, he continued. At his headquarters in Toronto, he met with escaped prisoner Robert Cobb Kennedy, folding him into a plan already stewing. It was originally suggested and planned by Col. Robert Martin, and funded by not only Thompson, but Confederate Senator Clement Clay.

The idea was for a group of eight, headed by Martin, to slip into New York City, book rooms at eight different hotels in the downtown district, and set them on fire, thus leveling much of the city. Each of the fires was to be set at 8pm, apparently to avoid the loss of life, as hotel guests would still be awake.

The plan quickly grew to almost hopelessly surreal proportions. “The tangible prospects were best for an uprising at Chicago and New York,” wrote John Headley, a Confederate spy integral to the plot, after the war. “The forces of the ‘Sons of Liberty’ were not only organized, but arms had been distributed. It had been deemed surest to rely upon the attempt to organize a Northwestern Confederacy with Chicago as the capital.” Other cities, such as Boston, Philadelphia, and Cincinnati were also on the list.

The strike against Chicago was thwarted on November 6, two days before the Presidential Election, but even prior to that, things began to fall apart.

Col. Martin believed that there were 20,000 armed Rebels in New York just waiting for the spark to bring about the revolution. These eight men selected to start the fires were also to take command of this army, which would then capture the Treasury and release the prisoners at Fort Lafayette.

The plan in both Chicago and New York was to happen on November 8th, Election Day. And so the eight conspirators left Toronto around October 25th, each through varying means. When they arrived in the city, they each stayed in separate hotels.

On October 29th, they met with a few comrades already in the city to discuss the finer details of the plot. “It was determined,” continued Headley, “that a number of fires should be started in different parts of the city, which would bring the population to the streets and prevent any sort of resistance to our movement.”


The agents already in New York reassured the eight that not only was they an army waiting for them, but that the Governor Horatio Seymour of New York “would not use the militia to suppress the insurrection in the city, but would leave that duty to the authorities at Washington. Indeed, we were to have the support of the Governor’s official neutrality. We were also told that upon the success of the revolution here a convention of delegates from New York, New Jersey, and the New England States would be held in New York City to form a Confederacy which would cooperate with the Confederates States and Northwestern Confederacy [in Chicago].”

All was quiet until November 3rd when the eight supposedly met with the private secretary of Governor Seymour. He assured them that Seymour was still on board and all would go according to plan.

With the Election coming, the very democratic city was filled with a party atmosphere, which the eight took advantage of. They visited theaters, museums, and even took part in a “monster torchlight procession” in support of George McClellan.

But a few days later, with the election drawing neigh, the paper announced that 10,000 Federal soldiers under Benjamin Butler had arrived to make sure New York City behaved itself. It changed everything.

“The leaders in our conspiracy were at once demoralized by this sudden advent of General Butler and his troops,” recalled Headley. “They felt that he must be aware of their purposes and many of them began to fear arrest, while others were defiant.” The agents in New York, supposedly orchestrating everything, were also taken aback. Ultimately, it was decided to postpone the plan. It was not, however, canceled.

The day before the election, the eight learned of the foiled plot in Chicago. As it was looking, there would be no revolution, no Northwestern Confederacy. As the days went by, they could see that plainly – nothing was happening anywhere.


Tired of waiting, Col. Martin begged the New York agents to allow them to go through with the plan anyway. They refused time and again, until they simply backed away and washed their hands of it.

“This left us practically at sea,” noted Headley. And soon they decided “to set the city on fire and give the people a scare if nothing else, and let the Government at Washington understand that burning homes in the South might find a counterpart in the North.”

The night before the planned attack, the 24th, the eight met and acquired their Greek Fire, which they would use to accelerate the blaze. Immediately they could see that they were in over their heads.

“None of the party knew anything about Greek fire,” admitted Headley, “except that the moment it was exposed to the air it would blaze and burn everything it touched.” They split up the small vials, numbering 144, and went their selected routes.

The next night, at 8pm, they attacked. Headley later described how he hit one of his targets:

“I reached the Astor House at 7:20 o’clock, got my key, and went to my room in the top story. It was the lower corner from room on Broadway. After lighting the gas jet I hung the bedclothes loosely on the headboard and piled the chairs, drawer of the bureau and washstand on the bed. Then stuffed some newspapers about among the mass and poured a bottle of turpentine over it all. I concluded to unlock my door and fix the key on the outside, as I might have to get out in a hurry, for I did not know whether the Green fire would make a noise or not. I opened a bottle carefully and quickly spilled it on the pile of rubbish. It blazed up instantly and the whole bed seemed to be in flames before I could get out. I locked the door and walked down the hall and stairway to the office, which was fairly crowded with people. I left the key at the office as usual and passed out [of the hotel].”

The scenes in two adjoining hotel rooms, as depicted by Harper's Weekley.
The scenes in two adjoining hotel rooms, as depicted by Harper’s Weekly.

Headley then went to the City Hotel and then Everett House, doing the same, before setting fire to a room in the United States Hotel. In all, nineteen hotels were hit. When Headley got back to Broadway, he saw a great commotion at Barnum’s Museum. “People were coming out and down ladders from the second and third floor windows and the manager was crying out for help to get his animals out. It looked like people were getting hurt running over each other in the stampede, and still I could not help some astonishment for I did not suppose there was a fire in the Museum.”

This was because there was not supposed to be a fire in the Museum. Robert Cobb Kennedy took it upon his own initiative to try and burn down Barnum’s. As the night wore on, the city discovered that it was on fire. A conspiracy was clearly under way, and the Rebels were obviously to blame.

The fires, however, were easily extinguished – as easily as normal fires. As the eight stood around watching the pandemonium heighten and then deflate, they concluded that the chemist who made the Greek fire for them must have purposely fouled the mix so it would cause little damage. In truth, it was due to the arsonists’ lack of knowledge about how fire worked. They closed all of the windows and doors, basically snuffing out the fires themselves.


And with that, they found new places to crash for the night and slept until late the next morning. Over brunch, they read of their exploits in the papers, a few even noticing that their detailed descriptions were given. Unmoved, they took a streetcar to Central Park where they “loafed, and read the afternoon papers.” While the city claimed to know of the plot, it became clear to them that it was a bluff.

That evening, they ate dinner and read more papers, and went to visit a friend. But before they entered the door, they were given a signal to stay clear – the authorities, it seemed were indeed on to them. “The last issue of the Evening Post gave such particulars as to almost designate our crowd,” wrote Headley. The article went on to give particulars that seemed frighteningly real.

The eight met up again that night and agreed to leave the city as quickly as possible. This they did, but not without a bit of panic and anxiety. Still, they arrived soon in Toronto and gave accounts to Jacob Thompson.

But that’s not the end of the story. Robert Cobb Kennedy grew restless in Canada and decided to reenter the United States so he could make his way back to his troops. Unfortunately for him, Federal authorities, through the word of a paid informant, knew the movements of at least some of the eight, and specifically Kennedy. As soon as he stepped off the train in Detroit, he was nabbed.

He did not go quietly, attempting to jump off the train taking him back to New York City. He was eventually brought before a military tribunal, charged with spying and violating the laws of war. None of the others were caught, and so the full brunt of the law was brought down upon him alone.

Robert Cobb Kennedy
Robert Cobb Kennedy

On March 20th, he was sentenced to be hanged, and five days later he was, though not before trying to break out of his cell prior to the event.

After the war, in 1866, Col. Robert Martin was arrested, but released due to lack of evidence. Most surprisingly of all, however, was the fate of John Headley. After the war, he returned to Kentucky and later served as its Secretary of State. In his memoirs, he confessed to the entire plot, but by that time nobody seemed to care that he was a part of it.

New York, of course, recovered, and soon the nation would have bigger things to worry about than a plot that failed due its conspirators knowing next to nothing about how to keep a fire burning.1

  1. Sources: Confederate Operations in Canada and New York by John W. Headley; True Crime in the Civil War: Cases of Murder, Treason, Counterfeiting by Tobin T. Buhk. []
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The Failed Confederate Plot to Burn New York City by CW DG is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 4.0 International


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