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Confederacy's Canadian Mission: Spies Across the Border
Stealing secrets and causing trouble, Rebel spies in Canada waged a risky underground war across the Union's northern frontier.
By Adam Mayers It seemed almost impossible now for a Confederate to leave Canada for the South without being followed by detectives," wrote Lieutenant John Headley, a Rebel secret agent in Canada. "But Lt. John Ashbrook and Capt. Robert Cobb Kennedy, attempted the journey."
The two Southern operatives had little choice. Someone had to carry information from the headquarters of Confederate covert operations in Toronto to the Confederate authorities in Richmond, Virginia. Indeed, many other undercover couriers already had. But now, in February 1865, moving about freely was difficult for Rebel spies. Ashbrook and Kennedy were being watched by the time they arrived at the train station.
"They got on the Grand Trunk Railway going west and crossed over to St. Clair Station in Michigan where they connected with a train going south and west of Detroit," wrote Headley.
"Kennedy took the first vacant seat, while Ashbrook found one near the front of the car. They had traveled for about an hour when Ashbrook, looking back observed two men enter and go straight to Kennedy. Without saying a word, they seized him.
"Ashbrook could not afford to wait. The two men had pistols drawn. One of them looked forward for a moment as if to locate him. The question was how to escape. He raised his window sash, put one leg out, ducked his head and went into the darkness. Fortune favored Ashbrook. He fell upon an embankment in the snow and rolled into a ditch. He had not sustained any injury. The train sped away leaving him in the darkness. He succeeded in finding a farmhouse and early next morning was conveyed across the country to a station on another railroad, where he caught a train and reached Cincinnati. Here he found friends and readily made his way across Kentucky to the Confederacy. The two men who arrested Kennedy were United States detectives who had gone all the way from Toronto with them."
Ashbrook eventually made it back to the South, but Kennedy was not so lucky. He was tried as a spy for his part in a Confederate plot to firebomb New York the previous November and hanged in April 1865.
With mishaps like the Ashbrook and Kennedy incident happening with increasing frequency, it was no wonder that Jacob Thompson, the director of Confederate secret operations in Canada, was at his wits' end. By early December 1864, his mission was a shambles. Traitors in his inner circle had been in the pay of the U.S. government for months. Key operatives had been captured and jailed. Others had blown their cover and were on the run. Just a few floors beneath his suite in a Toronto hotel, detectives staked out the bar. Across the street, at Toronto's main railway station, others noted the comings and goings of his contacts. Canadian authorities were so angry at what they believed was his abuse of their nation's neutrality that they considered jailing him. Signs of failure were everywhere.
"I had hoped to have accomplished more," the Mississippian mused bitterly in a letter written December 3, 1864, to Confederate Secretary of State Judah Benjamin. "But the bane and curse of this country is the surveillance under which we act. Detectives, or those ready to give information, stand on every corner."
Most of the core problems of Thompson's operation were his own. In the 2,300 years since unknown Chinese authors wrote The Art of War under the name Sun Tzu, the keys to successful spying had not changed much: discretion, stealth, a secure local base of operations, and an ample purse. Naive and indiscreet, Thompson was clearly the wrong man to head a spy mission. Although he had considerable skills as a politician and businessman, they were of little use in his role of spymaster. The one thing he did have was money. The Confederate States had given him some $600,000 to fund his mission, a fortune in his day, but he spent the money freely and foolishly as he pursued various schemes.
Six hundred thousand dollars may have sounded like a reasonable investment in early 1864, when the Confederacy set up operations in Canada with the goal of finding men to fill the thinning ranks of its armies. The Confederate government believed that many Confederate prisoners of war held in camps along the northern frontier had escaped and made their way to neutral Canada. In February, President Jefferson Davis sent James Holcombe to the province of Nova Scotia to round up stray escapees. Holcombe, a University of Virginia law professor, set up a network that would collect these men and get them to Halifax, the provincial capital. From there, they would be taken back to the South aboard blockade-runners.
While in Nova Scotia, Holcombe picked up rumors that discontent with the war was growing in the Union's Northwest, known today as the Midwest. These reports coincided with similar ones from other sources. Seeing an opportunity to stir things up to the South's advantage, Confederate authorities in Richmond sent Thompson and Clement Clay, a former U.S. senator from Alabama, to Canada in May.
Thompson kicked off his Canadian mission by sending a small guerrilla team south across the Canadian border to provide leadership for a Northwest rebellion to help finance it. The scheme would become known as the Northwest Conspiracy. Leading the uprising would be the so-called Copperhead groups, antiwar Democratic party organizations that Thompson wrongly believed to have well-organized armies numbering in the hundreds of thousands. They were supposed to be ready to overthrow the Union and form a new Northwestern Confederacy that would include Illinois, Indiana, Ohio, and Missouri. All they needed was some organizational help and some cash to pay for guns and ammunition. Thompson was only too happy to oblige. If a Northwest rebellion succeeded, the former United States would be broken into three pieces, and that should assure the Southern Confederacy's survival.
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