“New York Is Worth Twenty Richmonds”

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It was an ambitious plot. A small force of Confederate officers, smuggled into New York, was to set off a series of fires on Election Day as a diversion while Copperheads seized federal buildings and municipal offices, took control of the police department, freed prisoners from Fort Lafayette in New York Harbor, and threw the Army commander in New York, Major General John Adams Dix, into a dungeon. By sunset the Confederate flag would fly over City Hall. Following the success of the “revolution,” a convention of delegates from New York, New Jersey, and the New England states, where other insurrections were to be held, would be staged in New York to form a confederacy to cooperate with the government in Richmond. The plan appeared valid to Thompson. New York was a Copperhead city, its politics feeding on the downtrodden and the corrupt, its philosophy a mixture of states’ rights, appeasement, and outright support for the South. More than seven hundred thousand persons lived in the city, and they rejected Lincoln in 1860 by a two-to-one vote and would do so again.

The draft riots of July, 1863, had indicated how easily the embittered lower classes could be incited to riot and how ineffectual were New York’s small police force and the token federal detachment stationed there. Moreover, fire fighting was in the hands of 125 volunteer companies whose members seemed more interested in racing each other than in putting out blazes; they insisted on dragging their cumbersome equipment through the streets by hand instead of using horses.

Of vital importance to the Confederates was the existence in New York of an active ring of Copperheads of considerable power and influence. Prominent among them were the two Wood brothers, both congressmen who would later vote against the Thirteenth Amendment, which abolished slavery. Before the war they had run a lottery in Louisiana. Fernando Wood, the older of the two and one-time mayor of New York, was an immaculately dressed, pokerfaced corrupter who had risen to power on the shoulders of “two-penny” politicians; as mayor he had suggested, after the fall of Fort Sumter, that the city should secede from the Union. His brother Benjamin was publisher of one of the most virulent of anti-Lincoln newspapers, the Daily News , which had been instrumental in fanning the hatred that led to the draft riots.

There were others who were considered trustworthy, too: James A. McMaster, editor and publisher of the weekly Freeman’s Journal and Catholic Register ; Representative James Brooks, co-owner of the Evening Express ; Rushmore G. Horton, editor of the Weekly Day-Book ; and Hiram Cranston, proprietor of the New-York Hotel. In addition, it was believed that Governor Horatio Seymour, an opponent of abolition and the draft, might aid the plan.

The leader of the small Confederate band being sent to New York was Colonel Robert M. Martin of Kentucky. He and a fellow Kentuckian, Lieutenant John W. Headley, had served with the famed raider John Hunt Morgan. They had been sent by Richmond to Toronto that September to aid in military operations against the North. Martin, in his mid-twenties, had steel blue eyes and wore a mustache and goatee. He was six feet tall but walked slightly bent over because of a bullet wound in his right lung. Headley, whose memoirs were later to disclose the details of their exploits together, was known as Martin’s boyish-looking “assistant adjutant general.”

Besides Martin and Headley the group included Captain Robert Kennedy. Kennedy, a profane, hard-drinking Louisianian, had recently escaped from the military prison on Johnson’s Island; he had been wounded in the thigh during the Battle of Shiloh two years earlier and walked with a pronounced limp. All the others in the Confederate force were lieutenants—John T. Ashbrook, James T. Harrington, and James Chenault of Kentucky, John M. Price of Virginia, and a fifth whose name is unknown.

Greek fire was to be used. This was a mixture of phosphorus in a bisulfide of carbon that was commonly used in hand grenades, supposedly igniting spontaneously on contact with the air. It had been employed in an attack on shipping at St. Louis and in the St. Albans raid, though both times with unsatisfactory results. A Captain E. Longmire of Missouri was already in New York arranging for a supply of Greek fire when the eight Confederates, all in civilian clothes, boarded a train in Toronto in the last week of October. Each carried false papers.

After the Rebels arrived in New York, they immediately dispersed among several hotels and boarding houses to avoid suspicion. On Friday, October 28, with the national elections only ten days away, Martin, Headley, and Kennedy went to the Freeman’s Journal to make contact with their Copperhead liaison, McMaster. The publisher was a big man—six feet three—and his piercing eyes and deep voice suggested power. Encouraged by his boast that the Copperheads had enlisted “about twenty thousand” men and had already distributed smuggled-in arms, the Rebels assured him in turn of “open, bold, and unflinching action when the hour arrived for crucial duty.”