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.

The Lake Erie raid might have been a real success had Cole not been betrayed by a Confederate turncoat at Windsor. The informer was an officer who operated a hotel where 60 Confederate refugees lived. His guests were unaware they were boarding with a Union detective who relayed every conversation to Colonel Bennett Hill, the provost marshal of Detroit. Hill, in turn, passed the information on to the Michigan’s commander, Captain Jack Carter. It may even have been Thompson himself, lodging in Windsor just before the raid, who let information slip and sealed Cole’s fate.

In any case, on September 17, two days before the raid, Hill had wired Captain Carter and warned him of the plot to capture the Michigan: ‘It is reported to me that some of the officers and men of your steamer have been tampered with, and that a party of rebel refugees leave Windsor tomorrow with the expectation of getting possession of your steamer.’

On the morning of the 19th, Hill furnished the specifics that led to Cole’s arrest. ‘It is said that the parties will embark today at Maldon on board the Philo Parsons and will seize either the steamer or another running from Kelley’s Island,’ Hill wrote. ‘Since last dispatch I am again assured that officers and men have been bought by a man named Cole, a few to be introduced on board under the guise of friends of officers.’

Cole’s rooms were searched, and among his papers were found some letters linking him to Thompson. Other documents indicated he had been paroled in Memphis that April, after taking an oath not to take up arms against the Union. Both documents were enough to have him charged as a spy. If convicted, he would be executed.

Alerted to Cole’s predicament by Annie Brown, Thompson wrote a letter to the commandant of Johnson’s Island, where he believed Cole was incarcerated. He urged that Cole be treated as a prisoner of war rather than a spy. That would not get him out of jail, but it would keep him alive. It turned out that Cole was not at Johnson’s Island, however. He had been taken to a Federal prison in Cincinnati, then moved to Columbus, and finally to Fort Lafayette in New York Harbor. He was found guilty of treason and sentenced to hang, but a full confession earned him amnesty. He would be released in the spring of 1865.

A month after the Lake Erie raid, in October 1864, Canadian-based Confederates were back on the offensive, raiding the Vermont town of St. Albans. This time, however, Thompson was not involved–a symptom of yet another problem in his organization. The raid was authorized by Thompson’s second in command, former senator Clay. Sickly and ill-tempered, Clay deeply disliked Thompson. He had no interest in his boss’s plots and raids, and separated from him soon after they arrived in Halifax. While Thompson used Toronto and Montreal as his bases, Clay worked out of St. Catharines, a town on Lake Ontario about 15 miles from Niagara Falls. It was he who was responsible for the peace talks at Niagara Falls in July 1864. And it was he who was now launching one of the most politically controversial raids of the Canadian mission.

On October 19, 1864, about two dozen Rebel raiders commanded by Lieutenant Bennett Young, a Kentucky cavalry officer, descended on St. Albans, about 40 miles south of Montreal. They robbed three banks of up to $200,000, killing one man and wounding three other people. As they retreated, they unsuccessfully attempted to set fire to the town. Most of the raiders were quickly captured or eventually turned themselves in to Canadian authorities. Young was arrested at a farmhouse on the Canadian side of the border, and was about to be lynched by an angry mob of Vermonters when the timely appearance of a British soldier saved his life.

Young and his fellow raiders were accused of violating Canada’s neutrality. But they claimed that they operated with the official sanction of the Confederate government, and were therefore carrying out legitimate acts of war against the United States on U.S. soil, and merely residing in Canada. Despite challenges, the defense worked. Clay, however, did not linger to hear the verdict. He denied any responsibility for the raid and fled Canada for the South.

Next to bungling, Union spies, and internal division, one of the greatest factors in the failure of Thompson’s Canadian operation was deliberate betrayal from within the organization. The most reviled of Thompson’s turncoat operatives was Godfrey Joseph Hyams, an Arkansan who had traveled to Toronto in late 1863, after being forced to move, as he later told a Toronto court, by Federal soldiers who seized his property and expelled him from the state.

Hyams was apparently poor and uneducated. By late 1864, his wife was six months pregnant, and he was eking out a living repairing shoes. He was so hard up that when Thompson paid him $50 for a mission, most of the money went straight to rent in arrears. On February 22, 1865, Mrs. Hyams gave birth to a boy, who was christened Stonewall Jackson Hyams. Tragically, the baby died a month later, on March 20, and was buried at the cost of $1 in a Toronto Catholic cemetery.

Perhaps it is no coincidence that Hyams first appears in dispatches as an informer just a few weeks after his son’s death. On one hand, he loved the Confederate cause enough to name the boy after a revered Southern hero. On the other, he had no job prospects, and he was unable to pay the rent and buy basic necessities. His errands for Thompson had been dwindling, and along with it, his meager income. Soon any information he had would not be worth anything to anyone. It was a good time to sell out.

Whatever had caused his change of heart, on April 5, 1865, Hyams walked into the office of David Thurston, the U.S. consul in Toronto, and offered to make a deal. It appears he had first discussed the matter with Robert Harrison, Toronto’s crown attorney (a position similar to district attorney). At the time, Harrison was prosecuting numerous Thompson operatives on assorted charges. The defendants included the St. Albans raiders and Burley. It is possible that Hyams was questioned as part of those investigations and perhaps indicated a willingness to make a deal.

Thurston described Hyams’s visit in a letter to U.S. Secretary of State William H. Seward on April 7:

A few days since, a person named Hyams who has been an intimate associate of rebels here, called on me. He stated that he was in possession of important information. It related to the plans of those rebels and the steamer Georgian [a second plot to capture the Michigan and free prisoners at Johnson’s Island, involving a civilian vessel named Georgian]. He told me he had been connected with the rebels for several years and all their schemes and plots were known to him. He was desirous of communicating them to me if I would remunerate him for so doing. I said that the information would be submitted to the government of the U.S. and if it was considered of value, a proper recompense would be made, but under no circumstances could I guarantee it. He replied he was willing to accept those terms.

Hyams delivered high-grade information about the Georgian plan. An earlier report from a low-level Canadian informant known only as ‘Fides’ stated that Thompson had hired James Bates, a former Mississippi steamboat captain, as a front man to buy the Georgian. ‘[Bates] is a determined old fellow, an old maniac,’ Fides wrote. ‘His Captain knows the lake well and is a man to succeed. It behooves people of Sandusky to keep a good lookout.’ Hyams added to this, describing a falling out between Thompson and Bates and how Colonel George Taylor Denison, a Canadian army officer with Southern sympathies, had taken title of the ship for Thompson.

The most startling revelation was related to a secret arms factory in a Toronto house, where Thompson was making torpedoes, hand grenades, and so-called Greek fire, a crude ancestor of napalm. Authorities searched the property for evidence. Thurston later reported:

The house [Hyams] described was empty, but his belief was that certain of these incendiaries were buried under the floor. Two policemen were detailed to examine the premises and in the extremity of the hall a portion of the floor was removed and under four inches of water and 18 inches of earth, several torpedoes were found buried.

These torpedoes are covered with a mixture of broken coal and pitch and resemble pieces of bituminous coal. They are made of cast iron of irregular shape, hollow and are filled with powder and covered. Hyams says they are to be thrown into coal bins in factories and steamboats etc., where they will, without being noticed, be shoveled into the fire and effect the purpose for which they are designed.

Thurston relayed all this information to Toronto police, the Canadian attorney general’s department, and to Crown Attorney Harrison. Harrison responded that he hoped ‘to arrest Col. Thompson as being concerned in a conspiracy to violate neutrality laws.’ He also suggested that perhaps Hyams could provide valuable assistance in the prosecution of the St. Albans raiders. It may have been at this point that Canadian and U.S. officials decided to put Hyams on the payroll.

On April 10, just three days after Thurston wrote to Seward, the Confederate cabal was shocked when Hyams appeared as a witness for the prosecution at the trial of raid leader Young. Hyams told the court of his meetings with Young and the plans for the St. Albans raid. He named names and pointed fingers in the courtroom.

After the war, Hyams would continue his association with Federal officials, appearing as a witness in the Lincoln assassination trials. Prosecutors initially believed that the plot to kill Lincoln involved the Canadian commissioners because a bank draft found on John Wilkes Booth’s body was drawn on a Canadian bank. Although Booth had been in Montreal in the fall of 1864, it was not proven that the assassination plot involved Confederates in Canada.

The Hyams case and similar situations had made it clear that bad luck and Thompson’s ineptitude as a spymaster were stifling the Confederacy’s mission in Canada. The chasm between Thompson and Clay had done its share of damage, too. In a series of articles in Southern Bivouac magazine in 1886, the two men’s military commander, Captain Thomas Henry Hines of Kentucky, identified their interpersonal tension as a destructive factor:

The Commissioners were not harmonious from the inception of their mission. This was a source of constant embarrassment and proved one of the most potent obstacles for success. [They] found it impossible to agree.

Col. Thompson was a man of sterling integrity, but he was inclined to believe too much that was told to him, to trust too many men, to doubt too little and suspect less. His subordinates were kept in continual apprehension, lest he compromise their efforts by indiscreet confidences.

One of Hines’s close associates, Captain John Castleman, also wrote of the friction between Thompson and Clay in his memoir Active Service. Castleman thought highly of Thompson, but not of Clay. The latter ‘was not practical,’ wrote Castleman. ‘He lacked judgment. He was peevish, irritable and suspicious. He distrusted Mr. Thompson and relied on those who were often untrustworthy.’

The mutual animosity essentially turned Confederate operations in Canada into two missions with two masters who did not talk to each other, who often worked at cross purposes, and who no doubt compromised themselves in more ways than one. Meanwhile, Canadian and U.S. authorities were working together closely by late 1864, passing information back and forth in an effort to foil the espionage efforts. Canadians did not want to be drawn into America’s Civil War and came to resent that Thompson’s harassing actions were conducted from bases in their country. In the case of the Georgian, the United States/Canadian cooperation was particularly close. For the good of the Union cause, Canadian authorities impounded the vessel at Collingwood on Lake Huron, even though when they searched the vessel, they found no arms, munitions, or torpedoes.

By the end of 1864, it was obvious to Confederate authorities in Richmond that the Canadian mission was finished. Clay returned South in November, and on December 30 Secretary of State Benjamin ordered Thompson home: ‘From reports which reach us from trustworthy sources, we are satisfied that so close an espionage is kept upon you that your services have been deprived of the value which is attached to your residence in Canada. The President thinks that it is better that you return to the Confederacy.’

Thompson did not leave Canada until mid-April when he sailed for England. His wife joined him there, and they spent the next two years in Europe before returning to Mississippi. Clay turned himself in to Federal authorities and remained in prison until 1866. Fides and Hyams disappeared without a trace. Cole drifted to Mexico after he was freed from jail and then returned to Texas, where he reportedly went into the railroad business.

They could have made history, those fledgling spies who made up the Confederacy’s Canadian mission. Cast into the arena of international espionage, these would-be heroes had the chance to help rescue their cause from the brink of its demise. Unfortunately for them, and for the cause that counted on them, they failed miserably.

This article was written by Adam Mayers and originally published in the June 2001 issue of Civil War Times Magazine. For more great articles, be sure to subscribe to Civil War Times magazine today!