The Confederate Army of Manhattan was a group of eight Southern operatives who attempted to burn New York City on Evacuation Day, November 25, 1864, during the final stages of the American Civil War.
In a plot orchestrated by Jacob Thompson, the operatives infiltrated Union territory by way of Canada and made their way to New York City. On Friday night, November 25, beginning around 8:45pm, the group attempted to simultaneously start fires in 19 hotels, a theater, and P.T. Barnum's American Museum. The objective was to overwhelm the city's firefighting resources by distributing the fires around the city. The hotels included the primary hotels of the day, including the 5th Ward Museum Hotel, Astor House, the Belmont Hotel, the Fifth Avenue Hotel, the Howard Hotel, La Farge House, Lovejoy's Hotel, the Metropolitan Hotel, the St. James Hotel, the St. Nicholas Hotel, the Tammany Hotel, and the United States Hotel.)
Most of the fires either failed to start or were contained quickly. All the operatives escaped prosecution except Robert Cobb Kennedy, who was apprehended in January 1865 while trying to travel from Canada to the Confederate capital, Richmond, Virginia.
An article from February 28, 1865 describes Kennedy as follows:
Mr. Kennedy is a man of apparently 30 years of age, with an exceedingly unprepossessing countenance. His head is well shaped, but his brow is lowering, his eyes deep sunken and his look unsteady. Evidently a keen-witted, desperate man, he combines the cunning and the enthusiasm of a fanatic, with the lack of moral principle characteristic of many Southern Hotspurs, whose former college experiences, and most recent hotel-burning plots are somewhat familiar to our readers. Kennedy is well connected at the South, is a relative, a nephew we believe, of Howell Cobb, and was educated at the expense of the United States, at West Point, where he remained two years, leaving at that partial period of study in consequence of mental or physical inability. While there he made the acquaintance of Ex. Brig. Gen. E.W. Stoughton, who courteously proffered his services as counsel for his ancient friend in his present needy hour. 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.