This Week in Military History: November 24th – 30th

November 25th: The Confederacy Tries to Burn Down Manhattan

As the title indicates, this is not a story of a successful operation. It’s not even the story of an operation being beaten through guile and skill. It’s the story of a small group of incompetent secret agents who attempted an act of bitter revenge in response to a much more successful city-wide burning. So if you’re expecting a piece full of thrilling espionage action, we apologize in advance for your likely disappointment (perhaps you’ll be happier reading last week’s history article which was all about pirates). But it’s a pretty interesting historical footnote, so let’s dive in anyway.

Map of Manhattan, circa 1864.

The plot was the brainchild of a man named Jacob Thompson, one of the leaders of the Confederate Secret Service. Born in the town of Leasburg, North Carolina on May 10th, 1810, Thompson moved to Mississippi to open a law practice after passing the Bar in 1834. Interested in politics, he ran for Congress and won a seat in the House of Representatives in 1839. He won reelection several times before finally losing his office in 1851. He briefly returned to his lucrative law practice but was recalled to public service in 1857 when newly elected President James “Consistently Rated One of the Worst US Presidents” Buchanan asked Thompson to be his Secretary of the Interior.

The cabinet of President James Buchanan (fourth from left), 1859. Thompson is seated farthest left.

Buchanan’s term in office, covering the years preceeding the Civil War, was rife with arguments over slavery all over the country, including within his cabinet. For his part, Thompson was what was then considered a “moderate” on the issue of slavery, in so much as he approved of its practice but was strongly against reopening the trans-Atlantic slave trade. So he was a terrible person, but not a super-duper-extra terrible person. With the election of Abraham Lincoln in 1860 and the start of the secession of the southern states, Thompson was staunchly on the side of the burgeoning Confederacy.

1860 Presidential Campaign poster for Abraham Lincoln and his 1st term vice president, Hannibal Hamlin.

Appointed Inspector General of the Confederate Army and later commissioned a lieutenant colonel despite no prior military experience, Thompson served at several major battles in the western theater of the war. Then, in March of 1864, Confederate President Jefferson Davis asked Thompson to head up to Canada and lead secret operations from there. Thompson accepted and departed for Montreal. Once there, he quickly gained a reputation as something of a bogeyman in the northern states, with all sorts of submersive schemes attributed to him and his subordinates.

Photograph of Jacob Thompson taken sometime before the end of the Civil War.

His boldest plan came about as a direct result of General William Tecumseh Sherman’s famous and bloody Atlanta campaign from spring through the fall of 1864. Thompson, wishing to inflict a similar level of destruction of a northern city was was done to Atlanta, picked eight men to travel from Canada via Buffalo to Manhattan and set fire to landmarks and buildings across the city. It was meant to occur as the heavily contested Presidential Campaign of 1864 between the incumbent Lincoln and embittered ex-Army General George McClellan drew to a close, and coincide with coordinated uprisings by Confederate sympathizers across New York and in Chicago as well.

1864 Presidential Campaign poster for General George McClellan and George Pendleton.

But that initial plan fell through for a number of issues, not least of all because the plan had already leaked and was known of in Washington. Additionally, Union troops deployed en masse to most large cities in order to maintain order during the election. Their hopes for a widespread wave of chaos dashed, Thompson and his men decided to go through with the Manhattan arsons at a later date to dole out at least some modicum of revenge. They settled on November 25th, the day after Thanksgiving (which President Lincoln had made a recognized federal holiday the year before) and picked nineteen major hotels and a theater as targets.

Among them was the Astor House (sketched above in 1862), New York’s first and, at the time, most popular luxury hotel.

Armed with ten bottles of incendiary fluid apiece, the eight men (dubbed the “Confederate Army of Manhattan”) set about starting fires at every one of the chosen locations. As well as one more when one of the agents, Captain Robert Cobb Kennedy, got drunk and decided it would be funny to add P. T. Barnum’s (yes, that P. T. Barnum, the circus guy) American Museum to the list of places he was to burn down. The panic spread quickly across the city, but not for long. The saboteurs, thinking they were being cautious and sneaky, started most of the fires in rooms they then closed up and locked. This meant that the flames had little in-flowing oxygen to allow them to spread. The fire department put out the blazes quickly with minimal damage and not a single person injured.

Barnum’s American Museum, 1858.

All eight Confederate agents escaped back to Canada and, from there, made their various ways back to the south. Thompson, who had remained in Canada during and after the failed attack on Manhattan, fled to England for a while until things cooled off. He eventually returned to Mississippi to find the Union Army had burned down his home. But he saw no further consequences for his actions and died a wealthy man in 1884 at the age of 74. Only one of those responsible for the fires was ever caught: Captain Kennedy, who was apprehended in Detroit, imprisoned at Fort Lafayette in New York Harbor, and tried as a terrorist. Convicted, Kennedy was hanged on March 25th, 1865; the last Confederate soldier executed by the US during the war. A few months after that, the war itself was over. And the Confederate Army of Manhattan’s part mattered little in the grand scheme, one way or the other. But still: interesting historical footnote, as promised.

 Captain Robert Cobb Kennedy, Confederate Spy and Failed Circus Museum Burner.

And for those of you reading this with surprise that a Confederate force had attempted to strike as far up as New York City, you should know that it wasn’t even their northernmost attack.

The Confederate raid of St. Alban’s, Vermont on October 19th, 1864. Also an interesting historical footnote.