November 25, 1864 – Lieutenant John W. Headley and seven Confederate agents attempted to burn New York City in retaliation for Federal depredations in Atlanta and the Shenandoah Valley.
The Confederate Secret Service, based in Canada and led by Jacob Thompson (former U.S. interior secretary under President James Buchanan), had devised several plots to disrupt the Federal war effort and inspire northern Confederate sympathizers to join their cause. Most of these plots involved working with the Sons of Liberty, a Copperhead organization, to free Confederates from northern prison camps.
Prior to the Federal elections, a band of conspirators was formed to both overthrow Chicago leaders and burn New York. According to Headley:
“The tangible prospects were best for an uprising at Chicago and New York. 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.”
The idea to burn New York had been introduced by Colonel Robert C. Martin and suggested to Thompson by Robert C. Kennedy, an escaped Confederate prisoner. They believed that the fires would inspire the vast Copperhead population in the city to rise up while they freed the Confederates imprisoned at Fort Lafayette.
The original plan was to set fire to New York just before the election. The eight conspirators arrived in New York at different times and lodged in different hotels. Headley stated, “It was determined 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 conspirators believed that New York Governor Horatio Seymour–
“… 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.”
However, Major General Benjamin F. Butler deployed 10,000 Federal troops in New York just before the election to maintain order. Headley wrote, “The leaders in our conspiracy were at once demoralized by this sudden advent of General Butler and his troops. They felt that he must be aware of their purposes and many of them began to fear arrest, while others were defiant.”
The plot to take Chicago was foiled as well. Nonetheless, Martin insisted that the conspirators go through with burning New York, regardless of the election results. But the Confederate Secret Service refused, and as Headley wrote, “This left us practically at sea.” The agents therefore resolved “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.”
On the night of the 24th, the Confederates obtained 402 bottles of a highly flammable liquid called “Greek fire” from an elderly chemist. Headley stated, “None of the party knew anything about Greek fire, except that the moment it was exposed to the air it would blaze and burn everything it touched.” The conspirators planned to set fire to their hotel rooms, hoping that the flames would spread to other buildings until the entire city was burned in “one dazzling conflagration.”
The saboteurs set fire to 19 hotels, including the prominent Astor House. In addition, Kennedy set fire to Barnum’s Museum. City officials quickly determined that this was a Confederate plot, and just as quickly the fire department and private citizens extinguished the blazes. Their biggest challenge was to douse the flames at Barnum’s because the hay for the animals had caught fire.
Failing to destroy New York, the conspirators accused the chemist of blending an impotent batch of Greek fire. However, most of the perpetrators had failed to leave the doors and windows open in their hotel rooms when they set the fires, thus minimizing the ventilation needed for the flames to spread. When investigators began closing in on them, the conspirators left New York and returned to their headquarters at Toronto.
Kennedy later tried returning to his army unit, but Federal authorities arrested him at Detroit. A military tribunal convicted him of masterminding the plot to burn New York, and he was hanged in March 1865. Headley confessed to his role in the plot after the war but was not arrested. Martin, who devised the scheme but was not directly involved, was arrested after the war but acquitted due to lack of evidence.
The plot made sensational headlines, as reported in the New York Times:
“The plan was excellently well conceived, and evidently prepared with great care, and had it been executed with one-half the ability with which it was drawn up, no human power could have saved this city from utter destruction… But fortunately, thanks to the Police, Fire Department, and the bungling manner in which the plan was executed by the conspirators, it proved a complete and miserable failure.”
However, this failed effort did little to either damage New York or affect the war.
CivilWarDailyGazette.com; Cochran, Michael T., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 532; Denney, Robert E., The Civil War Years: A Day-by-Day Chronicle (New York: Gramercy Books, 1992 [1998 edition]), p. 492; Faust, Patricia L., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 322; Foote, Shelby, The Civil War: A Narrative: Volume 3: Red River to Appomattox (Vintage Civil War Library, Knopf Doubleday Publishing Group, Kindle Edition, 2011), Loc 15200-19; Fredriksen, John C., Civil War Almanac (New York: Checkmark Books, 2007), p. 523; Long, E.B. with Long, Barbara, The Civil War Day by Day (New York: Da Capo Press, Inc., 1971), p. 600-01; New York Times article of 27 Nov 1864; Time-Life Editors, Spies, Scouts and Raiders: Irregular Operations (Alexandria, VA: Time-Life Books, 1983), p. 62