How a Confederate officer planned to burn New York City to the ground

History · Published 1 October 2026 Swipe more like this →

In short: In November 1864, a group of Southern operatives launched a daring mission to cripple the Union's largest city. Using chemical firebombs, they aimed to destroy the Northern economy and avenge the scorched-earth tactics used against the South. It was a high-stakes plot of espionage that nearly ignited a catastrophe.

The plot was led by Robert Cobb Kennedy, a Louisiana planter’s son and Confederate officer. After escaping from a military prison on Lake Erie and fleeing to Canada, Kennedy joined other Southern exiles in Toronto. Driven by fury over General William Tecumseh Sherman’s scorched-earth campaigns in the South, the group sought to turn the tide of the Civil War through urban sabotage.

The group's initial strategy involved interfering with the 1864 presidential election by storming federal buildings and flying the Confederate flag over New York City Hall. However, after President Abraham Lincoln deployed federal troops to major cities to suppress unrest, the operatives pivoted to a more destructive method. Operating under false identities—Kennedy himself used the alias 'Mr. Stanton'—the group planned to simultaneously ignite firebombs in various hotels and businesses.

On the night of November 24, 1864, the attack commenced. The operatives used ten incendiary devices each, filled with 'Greek fire,' a chemical mixture believed to ignite upon brief exposure to air. While Kennedy planted bombs in three hotels and even tossed one into P.T. Barnum’s American Museum after a stop at a bar, the mission was a failure. Some devices failed to ignite, and the resulting small fires were quickly extinguished by the New York fire department.

The aftermath saw the six remaining attackers flee back to neutral Canada. While the North remained intact, the attempt sparked debate in the South. The Richmond Whig argued that New York should have been spared due to its economic ties to Southern cotton, suggesting instead that cities like Boston or Philadelphia were more deserving targets for retaliation.

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