At the head of the Confederacy’s Canada contingent was Jacob Thompson, who at one point had been U.S. Secretary of the Interior but resigned in protest a few months before the attack on Fort Sumter in South Carolina. As inspector general of the Confederate army, he supervised covert operations in Canada at the behest of Jefferson Davis himself. Thompson was eager to activate young men who’d found themselves in Canada and were bubbling over with ego, anger, and enthusiasm for the Southern cause—men like Robert Cobb Kennedy. When he came to Thompson’s attention, Kennedy was given a choice: He could try his best to get home to his family and farm, not knowing what condition he’d find them in, or he could become part of this gadfly secret service. “If it is in the service of my country,” Kennedy said, he would stay.
Kennedy agreed to sign on for the latest of Thompson’s plans, which called for small cells of Confederate operatives to travel to New York City, Chicago, and Boston. Once there they would use Election Day 1864 as an opportunity to commit violence, draw in local groups of Confederate supporters, and ultimately seize control of the cities. This was to be a crucial first step toward the formation of a Northern outpost of the Confederacy.
New York was of special interest to the operatives, since it seemed primed for their flavor of discord. The draft riots in 1863 had proven that the city’s population was volatile and that the police could be easily overwhelmed. There were many known Copperheads who might be receptive to Thompson’s plan, and both the mayor’s office and the Daily News seemed well in hand. Indeed, Confederate leaders said that they had been assured of Mayor Wood’s support for the action, noting in a report: “We were told that about 20,000 men were enlisted in New York under a complete organization; that arms had been provided already for the forces in the city, and we would be expected to take military supervision of the forces at the vital moment.”
In other words, operatives expected that, after they set fires across Manhattan, Copperheads in solidarity with their efforts would seize the chaotic moment to take over the city’s federal infrastructure and free Confederate prisoners from nearby Fort Lafayette. As for Major General John Adams Dix, a sometime rail baron, postmaster, and politician who commanded the Union army’s Department of the East, based in New York, the operatives hoped to toss him into the tiniest, clammiest cell they could find.