Confederacy’s Canadian Mission: Spies Across the Border

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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.

In the summer and fall of 1864, Thompson poured his best efforts into supporting and encouraging these groups. It soon became apparent, however, that they were vastly overestimated and poorly led. To make matters worse, Union spies and informers had infiltrated them. Key leaders were arrested, and when Union armies succeeded in capturing Atlanta in September 1864, the fire gradually went out of the Copperhead movement.

Meanwhile, Thompson’s team was moving on other fronts. In July, Clay and Holcombe were involved in secret Union-Confederate peace talks at Niagara Falls, Canada, with John Hay, an aide to President Abraham Lincoln. The talks were brief. Once Hay announced that Lincoln insisted on the full restoration of the Union as a condition for peace, there was nothing left to discuss. That condition was completely unacceptable to the Confederates.

Beginning in September of that year, Thompson turned to more overt acts of sabotage, including a series of cross-border raids from Canadian bases that he hoped would provoke Lincoln to invade Canada, which was a British colony at the time. He believed such an invasion would produce the same result as the Northwest rebellion would have: because the Union would not be able to sustain a war on two fronts, particularly against a world power like Great Britain, Lincoln would be forced to negotiate peace with the South.

One of the most ambitious of these raids was an operation on Lake Erie that Thompson authorized in mid-September. He planned for a raiding party–made up mostly of escaped Confederate prisoners of war–to seize the gunboat U.S.S. Michigan, which was anchored at Sandusky, Ohio, guarding Johnson’s Island Prison. The raiders were to board the ship, which would be rendered defenseless by infiltrators who would drug the crew with spiked champagne. Then, they would turn her guns on the prison, giving the 2,700 Confederate prisoners there a chance to escape. The escaped prisoners would form a foraging army and fight their way back to Virginia. The Rebel-controlled Michigan, meanwhile, would move down the lake, pounding Detroit, Cleveland, Buffalo, and Sandusky, Ohio, to rubble.

On September 19, the plan was put into action. At mid-morning a team of raiders seized the passenger steamer Philo Parsons for use in capturing the Michigan. The raiders steamed the Philo to the Bass Islands, about nine miles north of Sandusky. There, the passengers were put ashore after taking an oath not to raise the alarm. A second local steamer, the Island Queen, arrived at a critical moment and was also captured. Her passengers, including Federal soldiers on leave, took the same oath and were also put ashore.

The raiders towed the Island Queen offshore and scuttled her, while they pushed the Philo on toward Sandusky and the Michigan. The raiders expected a prearranged signal to assure them that the Michigan’s crew had been sedated, but that signal never came. Thompson’s inside man, Charles Cole, had been arrested earlier that day, foiling the operation.

Cole had spent a month in Sandusky with his mistress Annie Brown, pretending to be a Philadelphia banker. The pair wined and dined the officers of the Michigan with Thompson’s money, offering to host a lavish party aboard the gunboat on the 19th. But Cole had been exposed, and by the time the Philo arrived that day, he was under arrest and Annie was beating a hasty retreat to Toronto with the bad news. Far from being helpless, the Michigan was swarming with Union sailors and marines awaiting the attack.

After a tense few hours waiting for their signal, the Confederate raiders retreated. They sailed back across the lake flying a Confederate naval ensign, stripped the Philo of everything they could move, and scuttled her. A few weeks later, Canadian authorities arrested Confederate Acting Master Bennett Burley, second in command of the operation.

On its face a failure, the raid did cause considerable alarm along the Union’s northern frontier. Federal troops were sent to Buffalo, Sandusky, and Detroit as a precaution and remained on high alert. Meanwhile, Mayor William Fargo of Buffalo, New York, set up his own intelligence network, if only as an early-warning system.

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Tags: 19th Century, American Civil War, Civil War Times, Historical Conflicts

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