Thursday, April 16, 2026

How the ‘Confederate Army of Manhattan’ Tried to Burn Down New York City

The Civil War is considered the bloodiest conflict in U.S. history. On November 25, 1864, during its final stages, a group of eight Confederate rebel soldiers set fire to 19 hotels, a theater, and a museum in a failed attempt to burn down New York City. Their goal was to overwhelm the city’s firefighting resources by spreading fires across a wide area. Read on at manhattanyes.com to learn more about the background, causes, and consequences of this act of sabotage.

A Brief Overview of the War

The Civil War raged from April 1861 to May 1865 between the Confederacy (Southern states) and the Union (Northern states). The Confederacy rebelled against the Union due to economic and political reasons, with slavery being a central issue. The conflict ended in a Confederate defeat. Approximately 658,000 people died in the fighting, and another 420,000 were wounded. About 370,000 New Yorkers fought for the Union – that’s one in every five men in the state!

While the war didn’t solve every problem, it did resolve some key conflicts. Notably, the 13th Amendment to the U.S. Constitution, which abolished slavery, was ratified and took effect on December 18, 1865. The war also paved the way for accelerated industrial and agricultural development, the settlement of western lands, and a stronger domestic market.

Prelude to the Arsons

On November 8, 1864, Abraham Lincoln was re-elected President of the United States. Prior to this, the Lincoln administration had sent thousands of federal troops to New York City to ensure peaceful elections. Meanwhile, in the South, the Confederate government sensed defeat and resorted to guerrilla tactics in the North. A small number of Confederate officers traveled to New York City in the fall. With the city teeming with Union soldiers, Confederate agents could only blend into the crowds and watch the torchlight parades celebrating the election.

The Confederates hatched an ambitious plan for agents to infiltrate Northern cities, including Chicago and New York, and commit widespread arson. On Election Day, they plotted to seize federal buildings, acquire weapons from armories, and arm a mob of supporters. The rebels intended to raise the Confederate flag over City Hall and declare New York’s secession from the Union to join the Confederate government in Richmond. However, the New York City vote proceeded peacefully. The conspirators decided to postpone their uprising for a few weeks.

The Sabotage

On November 25, 1864, eight men walked the streets of Manhattan. The group called themselves the “Confederate Army of Manhattan.” Splitting up, the rebels checked into hotels from their predetermined lists. Shortly before 9 p.m., a room in the St. James Hotel was discovered to be on fire. Minutes later, a fire broke out at Barnum’s American Museum. Around the same time, four rooms were ablaze at the St. Nicholas Hotel. Soon after, Lafarge House, Metropolitan House, Brandreth House, Frenche’s Hotel, Belmont House, Wallack’s Theatre, and other buildings were also in flames. However, the fires were quickly extinguished.

Why Did the Plan Fail?

As The New York Times reported, the plan was brilliantly conceived and evidently prepared with great care. Had it been executed as originally intended, “no human power could have saved the city from destruction.”

The arsons were carried out using Greek fire – an incendiary mixture used in warfare during the Middle Ages. The rebels hired a retired druggist to prepare bottles of the flammable substance. They primarily targeted hotels to inflict maximum damage on the Broadway business district. It’s believed the soldiers began their operation in the evening, rather than at night, to give people a chance to escape. Their aim was to create chaos in the city, not to cause loss of life.

Greek fire is a concoction of quicklime, saltpeter, bitumen, sulfur, resin, and pitch. The rebels went from hotel to hotel, leaving the incendiary materials in rooms with closed windows and doors. This, ultimately, was their critical mistake. Greek fire needs oxygen to burn effectively, so in sealed rooms, it spread slowly or not at all.

Retribution

The Union immediately recognized the arsons as a Confederate plot, and authorities launched a manhunt for the perpetrators. Only Robert Cobb Kennedy was captured, apprehended in Detroit. His accomplices were more fortunate, successfully fleeing to Canada. A New York Times article from February 28, 1865, described Kennedy as “a man of about 30, of a most unprepossessing appearance.” He reportedly failed to complete his education at West Point due to “mental or physical incapacity.”

A Louisiana native and Confederate officer, Kennedy had escaped from Johnson’s Island military prison, where he was incarcerated, on October 4, 1864, and made his way to Canada. There, he joined a small group of Confederates. Confederate President Jefferson Davis had dispatched them to Canada to plan military raids that could be launched from politically neutral Canadian soil.

While awaiting trial, Kennedy made several incriminating “foolish confessions.” Before the executioner’s hood was placed over his head, the condemned man reportedly sang an old Irish drinking song ironically titled “Trust in Luck.” He confessed before his execution that the attempt to burn Barnum’s American Museum was “just a reckless joke,” something he did on a whim after having a few drinks.

The Northern attacks were orchestrated by former Mississippi Congressman Jacob Thompson, under orders from Jefferson Davis. Sent to Canada, Thompson spent the final year of the war futilely trying to organize mass Confederate escapes from POW camps in the Great Lakes region. He vehemently denied any involvement in the arsons in Northern cities. At the end of the war, Thompson and other Confederate leaders were accused of organizing Abraham Lincoln’s assassination.

However, Thompson’s complicity in these crimes was never proven in court. After the war, he fled to England and then to Canada. When things quieted down, he eventually returned to the States and settled in Memphis, Tennessee, where he managed his extensive properties and later died.

One conspirator who successfully evaded capture, John W. Headley, wrote about his exploits decades later. While some of his account seems embellished, his description of the November 25, 1864, fires generally aligns with newspaper reports. Headley confessed to setting fires in rooms at four separate hotels while his accomplices did the same in other buildings.

He began his part of the operation at the famous Astor House. According to Headley, he hung bed linens over the headboard and piled chairs, dresser drawers, and the washstand onto the bed. He then covered everything with newspaper, doused it with turpentine, and poured a bottle of Greek fire onto the heap. The bed immediately burst into flames. Headley fled the room, locking the door behind him. He followed the same method at the City Hotel, Everett House, and United States Hotel. Ultimately, the plot to burn the city appears to have been a bizarre sideshow in the war’s final year.

...