“New York Is Worth Twenty Richmonds”


One day in late October of 1864, as the Civil War was moving into its final stages, eight young men in civilian clothes arrived in New York City from Toronto by train. Though they spoke with southern accents, they were quickly caught up in the swirl of the city’s life, for there were thousands of Southerners in New York—businessmen and planters who had come north to protect their interests; families fleeing from ruin; and ex-Confederate soldiers, prisoners of war on parole, looking for a way to return home. If these eight men acted out of the ordinary at all, their behavior went unnoticed.


They were, in fact, Confederate officers, volunteers in a desperate plot to force the North to accept southern independence in return for peace. The story of how close they came to succeeding underscores a major dread of any nation at war within itself: sabotage by an enemy who looks and acts like a friend.

Earlier that year, in the spring, Jefferson Davis had charged three men with carrying out Confederate designs from across the Union’s weakest frontier, the more than one-thousand-mile border with Canada. Heading the mission was Colonel Jacob Thompson, a former aide to General P. G. T. Beauregard. A well-to-do Mississippian, Thompson before the war had been a congressman and Secretary of the Interior in Buchanan’s Cabinet.

Canada was decidedly pro-Southern, although officially neutral. Toronto, where Thompson made his headquarters, was full of southern refugees—Kentuckians, Missourians, Marylanders, and Virginians especially. The city was also the roosting nest of spies and informers. “The bane and curse of carrying out anything in this country is the surveillance under which we act,” Thompson complained in a letter to Confederate Secretary of State Judah P. Benjamin. “Detectives or those ready to give information stand at every street corner. Two or three can not interchange ideas without a reporter.” He warned against “any stranger who might claim an acquaintance, etc., as a swarm of detectives from the United States, male and female, [are] quartered in Toronto.”

Thompson nevertheless plotted on, convinced that “nothing but violence can terminate the war.” The result was a series of ill-conceived exploits, ail divulged in advance by informers at his elbow or spies behind his back. An elaborate scheme to promote a Northwest Confederacy was attempted in conjunction with Northern Copperheads, so-called “Peace” Democrats—and fizzled. Raids on Maine, the seizure of ships on the Great Lakes, the freeing of thousands of Confederate officers imprisoned at Johnson’s Island in Lake Erie, an uprising in Chicago timed to coincide with the Democratic National Convention, a financial crisis to be brought on by pushing up the price of gold -not one scheme succeeded. Worse still, a minor raid on St. Albans, Vermont, caused such a furor that Canada soon became a questionable port of refuge. [See “The Hit-and-run Raid,” A MERICAN H ERITAGE , August 1961.]

In a last-ditch attempt to stave off defeat, the Confederate government in 1864 set in motion a startling plan of destruction

Something approaching madness seemed to infect the schemes and the schemers. Surprisingly, Thompson was undeterred by the timidity shown by the Copperheads in the Midwest and grew no more cautious regarding his confidants despite the disclosures that stymied every operation. If anything, he was more determined than ever to succeed by the fall of 1864, for the war was going badly—Sheridan was devastating the Shenandoah Valley, and Sherman had seized Atlanta. Then, on October 15, an editorial appeared in the Richmond Whig and was reprinted in its entirety by the New-York Times . It said, in part: Sheridan reports to Grant that, in moving down the Valley to Woodstock, he has burned over two thousand barns filled with wheat, hay and farming implements, and over seventy mills filled with flour and wheat. … There is one effectual way, and only one that we know of, to arrest and prevent this and every other sort of atrocity —and that is to burn one of the chief cities of the enemy … and let its fate hang over the others as a warning of what may be done, and will be done to them, if the present system of war on the part of the enemy is continued. … New York is worth twenty Richmonds. …


Whether this was a signal from Richmond has never been determined. The idea of setting fire to New York and other northern cities had been considered for some time; the forthcoming Presidential election in the North, scheduled for November 8, provided the catalyst.