The September 11, 2001, attack on the World Trade Center towers left New Yorkers stunned and bloodied, but unbowed. It was not the first attempt against the buildings; in 1993 terrorists exploded a car bomb in the basement of one of the towers. At that time, Thomas McLarty, then President Bill Clinton’s chief of staff, said, ‘To my memory, we had never really experienced anything like this on American soil.’ In reality, terrorists had struck at Manhattan more than a century earlier.

In 1864 New York was the nation’s largest city and a world unto itself. When the Southern states seceded from the Union in 1861, some even called for New York City to follow suit and set itself up as a city-state, though it soon elected to stick with the North. At the time more than 814,000 people were crammed onto Manhattan Island, many of them living in near poverty around the slum of Five Points. A few small communities sprinkled the wilderness above 42nd Street, though far-sighted city fathers had purchased the land for Central Park back in 1856, and construction began as a relief project during the panic and depression of the following year. The water of the Hudson and East Rivers was clean enough that people could still swim in it, and they did.

Nevertheless, some things never change. ‘The greatest characteristic of New York is din and excitement,’ said The Stranger’s Guide to New York, a contemporary travel book. ‘Everything is done in a hurry, for all is intense anxiety. It is especially noticeable in the leading thoroughfare of Broadway, where the noise and confusion caused by the incessant passing and re-passing of some 18,000 vehicles a day render it a Babel scene.’ Broadway was indeed the city’s leading avenue. Large hotels stood on nearly every corner, and it was the street where legendary showman Phineas T. Barnum had purchased the old five-story Scudder’s Museum and renamed it Barnum’s American Museum. Here the master showman operated a spectacular place where people of all ages could marvel at his collection of the weird and wonderful or attended entertainments in the Lecture Room. ‘Three Mammoth Fat Girls, Weighing One Ton!’ Barnum’s notice in the New York Times for November 25, 1864, promised, as well as ‘Three Giants, Two Dwarfs, Indian Warriors, French Automatons, &c. Dramatic Entertainments Morning, Afternoon, and Evening.’

New York was also a city torn asunder by divergent politics. For three days in July 1863 it had erupted in protest against the draft, with lynch mobs running wild in the streets and rioters burning houses and businesses. Although the initial reports of more than 1,200 deaths proved exaggerated, as many as 118 people may have been killed before exhausted Union troops, marching straight from their victory at Gettysburg, put down the riot. In the aftermath, President Abraham Lincoln appointed Major General John Dix to oversee the military control of the city.

However, all that was in the past, and November 25, 1864, promised to be a day of celebration. For more than 80 years the date had been remembered as Evacuation Day, the day when the British abandoned New York City during the Revolutionary War. And this year it marked the first time the three famous acting brothers, Edwin Booth, Junius Booth, Jr., and John Wilkes Booth, had performed together. They were putting aside their own political differences to appear at the Winter Garden Theatre in Shakespeare’s play about an assassination, Julius Caesar. The production was a benefit to raise funds for a fine bronze statue of Shakespeare for Central Park.

Yet this Evacuation Day would be remembered for another reason. That evening Confederate agents planned to set New York City aflame. The plot had been concocted a few months earlier by Robert Martin, a former colonel under Confederate cavalry commander John Hunt Morgan (see ‘The Great Escape,’ February 2000). In 1864 Martin traveled to Canada to take part in the Confederate espionage operations being planned there. Like most acts of terrorism, the Confederacy hatched the New York operation as an act of retribution, a way to seek revenge for the Union’s ravaging of Virginia’s Shenandoah Valley, the breadbasket of the Confederacy. The plot was a simple one. Colonel Martin and seven other agents, dressed as civilians, would cross the Canadian border to aid in an uprising by Copperheads-Northerners who sympathized with the South-on Election Day, November 8. At a predetermined time, the agents would set fire to several of the hotels along Broadway, and the Copperheads would begin an uprising similar to the Draft Riots. Once they had captured General Dix and placed him in irons, they would raise the Confederate flag over the city and declare it an independent entity.

This audacious plot quickly fell apart. Union forces, tipped off by an informer, discovered the scheme, and troops under General Benjamin Butler marched into the city to maintain order. The quick action, plus the demoralizing news from Georgia that General William T. Sherman had captured Atlanta, deflated the Copperheads’ ambitious plans.

Nevertheless, the eight Confederates assigned to torch the city remained determined to complete their task. One by one, they made their way into New York City and registered under assumed names at various hotels, all of them along Broadway. John W. Headley, Martin’s second in command, contacted a local chemist from whom the Confederates had arranged to obtain 12 dozen bottles of a mixture that contemporary reports said was phosphorus. Other reports called it ‘Greek Fire,’ an incendiary mixture of sulfur, naphtha, and quicklime that bursts into flame when exposed to air. The mixture had a long history. The Ancient Greeks had invented it, and the Byzantines used it to destroy a Saracen fleet in the seventh century. For setting things ablaze, this was clearly the right stuff to use.

Headley found the chemist ‘in a basement on the west side of Washington Place.’ The old man handed him a heavy valise, and Headley lugged it onto a street car and took it with him to a rendezvous point. There he divided the bottles up among the other would-be arsonists, who put them in cheap black satchels. ‘We were now ready to create a sensation in New York,’ Headley declared.

The saboteurs struck on the evening of Friday, November 25. The first hotel they hit was the St. James on 26th and Broadway, where around 8:45 a guest saw smoke coming from a room that had been rented to a man calling himself John School. The locked door was broken down and the fire was put out in seconds. The room was empty, save for an empty bottle of Greek Fire in a black satchel.

The next hotel to report a blaze was the United States. A young man with a carpetbag had arrived that afternoon and asked for a room on a lower floor. The only one available was on the fifth floor, however, and the man agreed to take it ‘with great reluctance,’ reported the Times. The young man’s odd behavior, as well as his wig and fake whiskers, aroused the proprietor’s suspicions, or so he later said. But he rented the man a room anyway. At 8:45 someone discovered flames coming from the room, and the occupant had disappeared. Again, the fire was quickly extinguished.

A permanent resident of the St. Nicholas, a three-building hotel, noticed two men behaving suspiciously as they left the hotel. ‘It’s all right,’ one reassured the other before they both disappeared into the night. At 8:55 fires broke out in Rooms 128, 129, 130, and 174, but the house fire department kept the blazes under control and restricted damage to those four rooms. Then shortly after 9:00 an employee of Barnum’s Museum noticed a flash of fire on the fifth-floor staircase. His cry of fire ‘ran through the Lecture Room, startling everyone and causing the most intense excitement,’ said the New York Herald. ‘Almost before any of those in the Lecture Room could get out the fire had been extinguished, but this did not seem to allay the excitement . . . . The giantess became so alarmed that she ran down the main stairs into the street, and took refuge in Powers’ Hotel.’

At 9:20 a blaze erupted in a third-floor room of the Lafarge House, but guests and staff quickly extinguished it. The room’s occupant, one J.B. Richardson of Camden, New Jersey, was nowhere to be found. ‘When the alarm of fire was given at the Lafarge, the excitement became very intense among the closely-packed mass of human beings in the Winter Garden Theatre adjoining the Lafarge,’ said the Times. Edwin Booth, a police inspector, and a local judge helped calm the anxious audience.

The fires continued. A room at the Belmont Hotel was set ablaze around 10:00, and a room at Tammany Hall around the same time. The man who checked into the latter room, who gave his name as C.E. Morse of Rochester, had disappeared, but his handwriting resembled that of the man who had checked into one of the rooms of the St. Nicholas Hotel that had been set alight. Both blazes were quickly extinguished. Also at 10:00, residents of the Metropolitan discovered a fire on the upper floor, but hotel workers put it out. Around 10:30 someone opened the door to a fourth-floor bedroom on the northeast wing of Lovejoy’s Hotel and discovered a flaming mattress, but rapid action doused the blaze. At 11:00 in the New-England House, a man calling himself George Morse took a room on the second floor. ‘In a few minutes he came down stairs and went out, saying he would return,’ reported the Times. ‘Soon afterward the room which he occupied was found to be on fire.’ Here, too, the flames were doused quickly. Then at Lovejoy’s Hotel another room was discovered on fire, this time on the southeast wing. It was rapidly extinguished.

Headley set one of his fires in the plush Astor House. He put the bedclothes and furniture on the bed, added some newspapers, poured turpentine on the pile, then took out his Greek Fire. ‘I opened a bottle carefully and quickly, and 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,’ he wrote in 1906. Headley locked the door, casually made his way downstairs, and left his key with the clerk. He then set blazes at the Everett and United States Hotels. Walking down the street, Headley recognized another member of his gang, Captain Robert Cobb Kennedy, in front of him. ‘I closed up behind him and slapped him on the shoulder,’ Headley recalled. ‘He squatted and began to draw his pistol, but I laughed and he knew me. He laughed and said he ought to shoot me for giving him such a scare.’

The fires continued. A room on one of the upper floors of the Fifth Avenue Hotel burst into flames when a porter opened the door. The arsonist had saturated the bedding with phosphorous, but it didn’t ignite until the open door supplied the draft it needed. The porter extinguished the fire. At the five-story Hanford Hotel-which neighbored a planing mill and a large lumberyard-one of the upper floor rooms was found ablaze, but an employee put the flames out. Had the blaze spread, the entire Lower East Side might have been threatened. Meanwhile, the police discovered a couple of hay barges spitting fire, but they put them out without much difficulty.

Somehow the city’s luck continued to hold, despite the fact that some people kept ignoring all warning of calamity. ‘Immediately after the first alarm was given [Police Chief of Detectives John Young] went to the Metropolitan Hotel, told the proprietors what was anticipated, and urged them to set double watches through all the halls,’ reported the Herald. ‘He also sent similar messages to the other hotels, and had his advice been heeded, many of the fires would doubtless have been prevented.’ All in all, the saboteurs set more than a dozen buildings ablaze that night, but none of them burned long. That was mainly because the raiders, in their desire to remain undetected, made one major mistake: ‘It was noticed that in every room where the phosphorus was found the windows and all apertures for the admission of air and ventilation were tightly closed,’ the Herald reported. Without a draft, the fires didn’t have the oxygen they needed to reach dangerous levels.

New York City responded to the attack with fear and outrage. Frank Leslie’s Illustrated Newspaper called it ‘The most diabolical attempt at arson and murder of which there is any record in the history of our country.’ The Times called the plot ‘one of the most fiendish and inhuman acts known to modern times.’ P.T. Barnum quickly assured patrons with a statement that detailed his safeguards against future fires and said his museum was ‘as safe a place of amusement as can be found in the world.’

The following day, the police began rounding up suspects-nearly 200 people in all. Among them was a women from Baltimore whom police had taken into custody after she was ‘noticed going from one hotel to another, leaving each hotel just previous to the breaking out of the fire.’ She was later released after explaining she had merely been trying to track down a store clerk who was living at one of the hotels. While the Times called for stricter control of Southerners in the city, and the Hotel Keepers’ Association offered $20,000 in reward money for the apprehension of the arsonists, somehow all the Confederates managed to take trains out of town. They crossed back into Canada just two days later.

Robert Cobb Kennedy was not content to lie low in Canada. He was a man of action. A former West Pointer from Louisiana, Kennedy had maintained Southern sympathies and joined the Confederate army. Although captured and sent to the notorious Johnson’s Island Prison on Sandusky Bay, Lake Erie, Kennedy had escaped only six weeks before the New York attack. A contemporary at the prison remembered him as ‘a perfect dare-devil, and no situation, however perilous, seemed to daunt his courage.’ It was Kennedy who set the fire in the Barnum Museum, when he ducked into the building to hide after setting fire to his assigned hotels. Kennedy decided to burn the museum on a whim, feeling ‘there would be fun to start a scare,’ as Headley recounted. ‘He broke a bottle of Greek fire, he said, on the edge of a step like he would crack an egg. It blazed up and he got out to witness the result.’

Just two weeks after trying to set Broadway ablaze and crossing into Canada and safety, Kennedy involved himself in another covert operation-this time a plot to rescue seven Confederate generals being transferred between prisons by rail. This plot also failed, and soon after Kennedy returned to Canada he decided to make a break for his home state. This time his luck ran out. Detectives arrested Kennedy in Detroit and placed him on a train bound for New York City. There, in a military trial, judgment was swift and furious. ‘The attempt to set fire to the city of New York,’ said General Dix, ‘is one of the great atrocities of the age. There is nothing in the annals of barbarism which evinces greater vindictiveness. It was not a mere attempt to destroy the city, but to set fire to crowded hotels and places of public resort, in order to secure the greatest possible destruction of human life.’ And then the punishment was read: ‘Robert C. Kennedy will be hanged from the neck till he is dead at Fort Lafayette, New York Harbor, on Saturday, the twenty-fifth day of March.’

On that day Kennedy stood on the gallows, and a hood was placed over his head. He began singing: ‘Trust to luck/trust to luck/stare Fate in the face/for your heart will be easy/if it’s in the right place . . . ‘ Then the platform dropped. He was the last Confederate soldier executed by the Union.

‘Though the damage was minor, as it turned out,’ Civil War historian Shelby Foote wrote, ‘the possibilities were frightening enough. Federal authorities could see in the conspiracy a forecast of what might be expected in the months ahead, when the rebels grew still more desperate over increasing signs that their war could not be won on the field of battle.’ Life in New York quickly returned to normal, so much so that an editorial writer for the New York Times believed that the city had not learned its lesson. ‘The effective measures taken by the authorities will cause a temporary suspension of incendiary operations, no doubt,’ he wrote, ‘but it becomes us to see to it that we are not put off our guard by relapsing into a somnolent indifference. It is when we have got to fancy ourselves perfectly secure, that the pestilence will break out with new and accumulated force.’

This article was written by Phil Scott and originally published in the January 2002 issue of American History Magazine. For more great articles, subscribe to American History magazine today!