The Confederate Attack on New York

When the Civil War began to turn against the Confederates in 1864, they began to desperately search for ways to “take the war to the north”, both to exact a measure of revenge for William T Sherman’s destructive march across the South, and to create havoc and panic among the Yankees. And one of these was a planned firebombing campaign in New York City.

robert cobb kennedy
Robert Cobb Kennedy, just before his execution    photo from WikiCommons

By 1862, there were already a number of different Confederate secret services attempting to carry out spying, sabotage, and clandestine attacks on the North. Some of these operated under the control of the Confederate Secretary of War, some under the Secretary of State, and some under the direct orders of the Confederate military. One of these networks, organized under Confederate War Secretary Stephen Mallory and given the diplomatic cover name of “The Confederate Mission to Canada”, had already established a partisan network across the border in Montreal under the command of Jacob Thompson—who had formerly been Secretary of the Interior for the US Government. The Union had placed a number of POW camps in Ohio and New York, near the border with Canada, and the Mission had smuggled in a number of Confederate volunteers to attempt to carry out cross-border raids to free these captured prisoners. All of these attempts failed, however, and only provoked an official diplomatic protest from the US to Canada about the “enemy forces” sheltering along its border.

So instead, the Mission saboteurs turned to another target: New York City. Politically, New York was a heavy supporter of the Democratic Party. In particular, the faction known as “Copperheads”, which opposed Lincoln’s Republican Party and advocated for a negotiated end to the war, was strong in the city. Thompson hoped that a bold stroke here might demoralize Lincoln’s supporters and encourage the Copperheads in their efforts to end the war.

Remarkably, we know a lot about how the Confederate attack on New York was planned and carried out, because one of the participants—named John Headley—wrote an account of it in his memoirs after the war. Other details came from the trial of one of the saboteurs, Robert Cobb Kennedy, who was captured.

The plot hatched by the Confederate Mission to Canada was targeted at the political situation in the United States. In the months leading up to the election of 1864, the war was not going particularly well for the North. General Sherman was stalled in Georgia, and General Ulysses Grant was taking huge casualties in Virginia. Many people—including Abraham Lincoln—had serious doubts as to whether Lincoln could win the upcoming election against his opponent, the former Union Army General George B McClellan, who was running as a pro-peace Copperhead. The Confederates hoped to disrupt the election, help McClellan win, and gain a negotiated settlement that would grant independence to the South.

Their plan was impossibly ambitious. They would smuggle a large number of Confederate operatives, many of them escaped POWs or experienced guerrilla raiders, into Canada, and just before the elections these sabotage teams would cross into the US, infiltrate into major cities like New York, Boston and Chicago, and launch an armed rebellion by seizing the armories and distributing weapons to what they presumed would be large crowds of Southern sympathizers.

In the end, just one Confederate band was able to successfully enter the US: a group of eight men, grandly styling themselves as “The Confederate Army of Manhattan” and commanded by Lieutenant Colonel Robert Martin, made their way to New York City on November 8, but found the city flooded with Federal soldiers. The Union counter-intelligence service had already gotten wind of the Confederate plot: the troops were also a precaution prompted by the deadly anti-war draft riots that had occurred earlier in the city. New York was being patrolled by 10,000 men under General Benjamin Butler. As Headley later wrote, “We remained in the city awaiting events, but the situation being chaotic we had nothing to do.” The planned Confederate uprising fell flat on its face. The election went off without any incidents, and although New York City voted against him, Lincoln won re-election.

So, the “Army of Manhattan”, still in New York City, came up with another idea. One of the group had somehow obtained a number of firebombs filled with a liquid phosphorus concoction that would burst into flame upon contact with air. The new plan, which was hastily improvised after testing out the bombs in Central Park, was for six saboteurs to spread out across town and, at an agreed-upon time, ignite their incendiaries and start a series of simultaneous fires. At this time, most buildings in New York City were made of wood, and any large fire in the crowded structures would spread quickly from block to block, and presented a serious danger to the entire city.

The attack took place on the evening after Thanksgiving in November 1864. Each of the conspirators rented rooms in a number of different prominent hotels, and systematically set off their firebombs by piling up their furniture and mattresses and soaking it with their liquid incendiary. To prevent the smoke from being immediately detected—and thereby give the fires enough time to become well-established and spread—the saboteurs carefully sealed up each room, closing all the windows and putting cloth along the bottom of the doors. In his confession, Headley noted that he himself set fires in four different hotels. Kennedy also ignited several hotels, and then went to the popular PT Barnum Museum, which was packed with tourists, and set off a firebomb in one of the stairwells. Other targets were Niblo’s Garden and the Metropolitan Theater. In all, the Confederates managed to start nineteen fires across the city, most of them along Broadway. In a historic irony, the fire at the LaFarge Hotel managed to disrupt a performance of Shakespeare’s “Julius Caesar” at the Winter Garden Theater next door—starring the famous actor John Wilkes Booth.

It could potentially have been a major disaster. But the saboteurs had made an amateur mistake: by setting off the fires inside a sealed room, they cut off the airflow, and most of the fires merely smoldered slowly until they used up all the oxygen and then went out. The few that managed to catch alight were quickly put out. There were no deaths or injuries.

The following night, after seeing the newspaper reports of their unsuccessful attacks, the eight members of the “Confederate Army of Manhattan” all took trains out of town, passing through Albany to Buffalo and then on across the Canadian border.  A couple of months later, they re-entered the US and made their way south. Seven of the eight successfully made their way to Confederate territory. Kennedy, however, had apparently made some drunken boasts in Canada about his role in the attack and was identified by Union intelligence agents. He was caught at the Canadian border and was taken to Fort Lafayette in New York, charged with arson and treason. Here, he continued his boasting and bragging, with one newspaper account noting, “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.” In the end, Kennedy confessed to the whole thing, providing details of the plot (though he repeatedly refused to disclose the names of any of his fellow saboteurs). He was hanged in New York on March 25, 1865.



3 thoughts on “The Confederate Attack on New York”

  1. I wonder if Kennedy was related to the later famous Kennedy dynasty.
    In any event, it’s a good question whether successfully burning down half of New York might not have backfired on the saboteurs, by turning pro-peace folks into vehemently anti-south, pro-war people. It’s not like 9/11 exactly motivated Americans to become pro-peace with Islam; guerrilla attacks frequently do precisely the opposite of what the attackers intended.

    1. In addition, New York was already mostly anti-war anyway. Doesn’t seem to be much point in attacking people who are mostly on your side. It doesn’t seem that the Confederates really thought this thing through very well. 😉

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