By Walter Giersbach

On Nov. 25. 1864, eight men walked the streets of Manhattan, New York. The group, calling themselves the Confederate Army of Manhattan, split up and approached a series of hotels on their lists and checked in.

“At 17 minutes of nine the St. James Hotel was discovered to be on fire in one of the rooms,” The New York Times reported. Bedding and furniture had been saturated with an accelerant and set aflame. A few minutes later, Barnum’s Museum was ablaze. About the same time, four rooms of the St. Nicholas Hotel were ablaze. By 9:20 p.m. a room in the Lafarge House was ln flames. Then the Metropolitan House, Brandreth House, Frenche’s Hotel, the Belmont House, Wallack’s Theatre and several other buildings were on fire. Included in the incendiary maelstrom were 5th Ward Museum Hotel, Astor House, the Belmont Hotel, the Fifth Avenue Hotel, the Howard Hotel, La Farge House, Lovejoy's Hotel, the Metropolitan Hotel, the St. James Hotel, the St. Nicholas Hotel, the Tammany Hotel, and the United States Hotel. [1]


The 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 alarms sounded. They would meet again the next evening, and make their way back to Canada. [2]

Confusing and Impulsive Plan

The original plot was hatched as Lincoln’s election neared. The rebels would occupy federal buildings, obtain weapons from arsenals, and arm a crowd of supporters they assumed would rise to the rebellion. The insurgents would then raise a Confederate flag over City Hall and declare that New York City had left the Union and had aligned itself with the Confederate government in Richmond.

By some accounts, the plan was said to be developed enough that Union double-agents heard about it and informed the governor of New York, who refused to take the warning seriously.

The handful of Confederate officers entered the United States at Buffalo, New York, and traveled to New York in the fall. But their plans to disrupt the election, which was to be held on Nov. 8, 1864, were thwarted when the Lincoln administration sent thousands of federal troops to New York to ensure a peaceful election. The reelection of President Lincoln was in doubt that summer. The nation was weary of the war, the Confederates felt, and factions in the North were antagonistic to the fighting. In the South, the Confederate government would smell defeat and was motivated to create harassment in the North by guerrilla action. At least, they could create disturbances like the draft riots in New York City the previous year.

But the city was crawling with Union soldiers, so the Confederate infiltrators could only mingle in the crowds and observe the torchlight parades organized by supporters of President Lincoln and his opponent, Gen. George B. McClellan. On election day the voting went smoothly in New York City. Although Lincoln did not carry the city, he was elected to a second term. [3]

The New York raiders weren’t done, though. They got back together, and agreed to attempt their strike again in another 10 days. But, by this time two of their number had lost heart and deserted. The incendiary plot was delayed but not deferred until later in the month

Capt. Kennedy: Wild Card

Barnum’s Museum, across from the Astor, was also set ablaze when Capt. Robert Cobb Kennedy, a drinking man, tossed a bottle of the accelerant and departed.

Robert Cobb Kennedy

There was an element of capriciousness in the sabotage. A New York Times article from Feb. 28, 1865, describes Kennedy as “a man of apparently 30 years of age, with an exceedingly unprepossessing countenance.

“His head is well shaped, but his brow is lowering, his eyes deep sunken and his look unsteady. Evidently a keen-witted, desperate man, he combines the cunning and the enthusiasm of a fanatic, with the lack of moral principle characteristic of many Southern Hotspurs, whose former college experiences, and most recent hotel-burning plots are somewhat familiar to our readers. Kennedy is well connected at the South, was a relative, a nephew it’s believed, of Howell Cobb, and was educated at the expense of the United States, at West Point, where he remained two years. He left his studies unfinished because of mental or physical inability. While there he made the acquaintance of Ex. Brig. Gen. E.W. Stoughton, who courteously proffered his services as counsel for his ancient friend in his present needy hour. During Kennedy’s confinement here, while awaiting trial, he made sundry foolish admissions, wrote several letters which have told against him, and in general did, either intentionally or indiscreetly, many things, which seem to have rendered his conviction almost a matter of entire certainty.”

A Louisiana native and Confederate officer, Kennedy escaped from Johnson’s Island Military Prison, where he had been incarcerated, on Oct. 4, 1864, and made his way to Canada. There, he joined with the small group of Confederate officers. The group had been dispatched to Canada by Confederate President Jefferson Davis’ administration to plan military raids that could be launched from politically neutral Canadian soil.

Prior to his execution he claimed that the attempt to set fire to the American Museum was “simply a reckless joke.… There was no fiendishness about it. The Museum was set on fire by merest accident, after I had been drinking, and just for the fun of a scare.” He and his fellow “incendiaries” had escaped to Canada after their plan failed. Kennedy alone was captured when he tried to sneak back into the United States at Detroit. He was tried, convicted, and executed on March 25, 1865, at Fort Lafayette in New York harbor. Kennedy was the only rebel invader who was captured, tried, convicted and executed.

Retribution for Northern Attacks

A grandiose plan was devised to infiltrate the Confederate agents into northern cities, including Chicago and New York, and commit widespread acts of arson. In the resulting confusion, it was hoped that southern sympathizers, including the Copperheads, could seize control of important buildings in the cities.

The original plot for New York City, as outlandish as it seems, was to occupy federal buildings, obtain weapons from arsenals, and arm a crowd of supporters. The insurgents would then raise a Confederate flag over City Hall and declare that New York City had left the Union and had aligned itself with the Confederate government in Richmond. [4]

Thus began one of the audacious attempts at retribution as Southern forces retreated in the closing days of the War Between the States.

The plan was to foment an uprising among the war-weary Union supporters; Copperheads, the Order of American Knights; and their Sons of Liberty faction. The Confederates also counted on the support of the Confederate President Jefferson Davis.

They traveled by sea to Canada then crossed south to the United States.

The group of eight rebel soldiers started fires in more than 20 locations in an unsuccessful attempt to burn down New York City. Their plan was to burn New York on or after Evacuation Day (Lincoln-Johnson victory vs. McClellan-Pendleton), on Nov. 25, during the final stages of the American Civil War.

The Rebels had contracted a retired druggist to make 12 dozen four-ounce bottles of a volatile incendiary substance known as “Greek fire.” John W. 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.”

The ”Greek fire” was a mixture of quicklime, saltpeter, bitumen, sulfur, resin and pitch. This incendiary fluid has been used since medieval times. The rebels went from hotel to hotel, piling combustible materials, closing windows and locking doors, and leaving. What they hadn’t realized was that the Greek fire required oxygen to burn, and the fires spread slowly if at all, in the airless rooms. [5]

Brains Behind the Plot

Hon. Jacob Thompson, architect of destruction

The Northern attacks were orchestrated by former Mississippi Congressman Jacob Thompson. Thompson was a promising politician who had been associated with President James Polk’s campaign and, earlier, turned down President Franklin Pierce’s offer of the Havana consulate. Back in Mississippi Thompson made a half-hearted race for governor before undertaking military service.

His army career ended when, as inspector under Lieutenant General John C. Pemberton, he was captured at Vicksburg and paroled. Elected to the Mississippi legislature in the fall of 1863, Thompson was summoned to Richmond by Confederate President Jefferson Davis.

Sent to Canada, Thompson spent the last year of the war vainly attempting — with or without Copperhead support — to arrange mass Confederate escapes from prisoner-of-war camps in the Great Lakes area. He steadfastly disavowed any complicity in plots to burn Northern cities and maintained that the 1864 raid on St. Albans, Vt., was carried out against his orders.

At the close of the war, he and other Confederate leaders were charged with co-conspiracy in the Lincoln assassination, and a $25,000 reward was posted for his capture. Considering these consequences. Thompson and his wife spent several years in England before it was safe for them to return, first to Oxford, where their home had been destroyed in the war, and shortly thereafter to Memphis, Tenn. [6]

Thompson returned to public notice in the 1870s when the scandal-beset Grant administration sued him for $2 million to recover the Floyd-Bailey losses. Clearly a partisan effort to divert attention from the War Department's Belknap scandals, the suit was quietly dropped after the 1876 election. However, no one has explained the sources of family’s affluent postwar lifestyle. Had he indeed invested his wife's dowry — “a trunk full of gold,” according to family tradition — in English securities, or had he embezzled Confederate funds entrusted to him in Canada?

An ambitious, calculating man, Jacob Thompson remains an obscure figure in the face of his earlier prominence in Mississippi and Washington. On his death in Memphis he left behind remarkably little material on which to base a definitive study of his career.

Nighttime Attack

On Friday night, Nov. 25, beginning around 8:45pm, the group attempted to simultaneously start fires in 19 hotels, a theater, and P.T. Barnum's American Museum. The objective was to overwhelm the city's firefighting resources by distributing the fires around the city. The hotels included the primary hotels of the day, including the 5th Ward Museum Hotel, Astor House, the Belmont Hotel, the Fifth Avenue Hotel, the Howard Hotel, La Farge House, Lovejoy's Hotel, the Metropolitan Hotel, the St. James Hotel, the St. Nicholas Hotel, the Tammany Hotel, and the United States Hotel.

Most of the fires either failed to start or were contained quickly. All the operatives escaped prosecution except Robert Cobb Kennedy, who was apprehended in January 1865 while trying to travel from Canada to the Confederate capital, Richmond, Virginia.

An article from Feb. 28 New York Times describes Kennedy as “a man of apparently 30 years of age, with an exceedingly unprepossessing countenance. His head is well shaped, but his brow is lowering, his eyes deep sunken and his look unsteady. Evidently a keen-witted, desperate man, he combines the cunning and the enthusiasm of a fanatic, with the lack of moral principle characteristic of many Southern Hotspurs, whose former college experiences, and most recent hotel-burning plots are somewhat familiar to our readers. Kennedy is well connected at the South, is a relative, a nephew we believe, of Howell Cobb, and was educated at the expense of the United States, at West Point, where he remained two years, leaving at that partial period of study in consequence of mental or physical inability. While there he made the acquaintance of Ex. Brig. Gen. E.W. Stoughton, who courteously proffered his services as counsel for his ancient friend in his present needy hour. During Kennedy’s confinement here, while awaiting trial, he made sundry foolish admissions, wrote several letters which have told against him, and in general did, either intentionally or indiscreetly, many things, which seem to have rendered his conviction almost a matter of entire certainty.”

A Louisiana native and Confederate officer, Kennedy had escaped from Johnson’s Island Military Prison on October 4, 1864, and made his way to Canada. There, he joined with the small group of Confederate officers who had been dispatched to Canada by Confederate President Jefferson Davis to plan military raids that could be launched at the Union from politically neutral Canadian soil.

Fort Lafayette in New York Harbor, where Robert C. Kennedy was executed. (Credit Library of Congress). Fort Lafayette was an island coastal fortification in the Narrows of New York Harbor, built offshore from  Fort Hamilton at the southern tip of what is now Bay Ridge in the borough of Brooklyn. [7]

Prior to his execution he claimed that the attempt to set fire to the American Museum was “simply a reckless joke… There was no fiendishness about it. The Museum was set on fire by merest accident, after I had been drinking, and just for the fun of a scare.” He and his fellow “incendiaries” escaped to Canada after their plan failed, and Kennedy alone was captured when he tried to slip back into the United States at Detroit. He was tried, convicted, and executed on Mar. 25, 1865, at Fort Lafayette in New York harbor.

Panic in the Streets

The night did not go as planned. Friday Nov. 25, 1864, was the night after Thanksgiving, conspirators set their fires in 13 major hotels in Manhattan, as well as in public buildings such as theaters and one of the most popular attractions in the country, the museum run by Phineas T. Barnum.

Crowds poured into the streets during the simultaneous attacks, but the panic faded when the fires were quickly extinguished. The chaos was immediately assumed to be some sort of Confederate plot, and the authorities began hunting for the perpetrators. Further, the city was full of troop because of the election. [8 ]

Though the Confederate agents later claimed they didn’t mean to take human lives, one of them, Captain Robert C. Kennedy, entered Barnum's Museum, which was packed with patrons, and set a fire in a stairwell. A panic ensued, with people rushing out of the building in a stampede, but no one was killed or seriously injured. The fire was quickly extinguished.

In the hotels, the results were much the same. The fires did not spread beyond any of the rooms in which they had been set, and the entire plot seemed to fail because of ineptitude.

As some of the conspirators mixed with New Yorkers in the streets that night, they overheard people already talking about how it must be a Confederate plot. And by the next morning newspapers were reporting that detectives were looking for the plotters. [9]

Shortly afterwards, thousands of federal troops marched into New York with General Butler and 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.

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.”

One of the conspirators who participated in the plot and successfully evaded capture, John W. Headley, wrote about his adventures decades later. While some of what he wrote seems fanciful, his account of the setting of fires on the night of November 25, 1864 generally aligns with newspaper reports.


Headley said he had taken rooms in four separate hotels, and the other conspirators also took rooms in multiple hotels. They had obtained a chemical concoction dubbed “Greek fire” that was supposed to ignite when jars containing it were opened and the substance came into contact with the air. [10]

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.

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. Overall, 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, the saboteurs 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 Mar. 25, 1865 – just weeks before the cessation of hostilities – he was hanged at Fort Lafayette. Before the hood was placed over his face, Kennedy tremulously sang an old Irish drinking song ironically titled, “Trust in Luck.”

Had the original plot gone forward to disrupt the election and create a Copperhead rebellion in New York, it’s doubtful it could have succeeded. But it might have created a diversion to pull Union troops away from the front, and it’s possible it could have had an impact on the course of the war. As it was, the plot to burn the city was an odd sideshow to the final year of the war.

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Show Notes

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© 2024 Walter Giersbach

Written by Walter Giersbach.

About the Author:
Walter Giersbach’s fiction has appeared in a score of online and print publications. He also writes extensively on American history, with 10 pieces published in Military History Online. Two volumes of short stories, Cruising the Green of Second Avenue, published by Wild Child (www.wildchildpublishing.com) were available from online retailers until his publisher ceased operations. He served for three decades as director of communications for Fortune 500 companies, helped publicize the Connecticut Film Festival, managed publicity and programs for Western Connecticut State University’s Haas Library, and moderates a writing group in New Jersey.

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