Confederate Operations in Canada

        From the earliest days of the Civil War the Confederacy had a secret operation in Canada with two main purposes. First, Canada provided a safe haven for Confederate prisoners of war who escaped from the prison camps in the North, and second, it served as a relay point for communications between England and the Confederacy. During the early days of the war Rose O'Neal Greenhow, of Washington, served as an intermediary between Washington and Toronto.
        On 7 April 1864, the mission of the Toronto operation was drastically changed. On that day President Jefferson Davis sent the following telegram to the Honorable Jacob Thompson, in Mississippi:  "If your engagements permit you to accept service abroad for the next six months, please come here immediately." Mr. Thompson, a lawyer, statesman, ex-member of Congress, and Secretary of the Interior under President Buchanan, was above all a loyal Confederate. He quickly responded to President Davis call.
        The reason for his summoning by President Davis was that the Confederacy, in a last desperate action, wanted Thompson to go to Canada and from there direct a secret operation to create hostile activities in the Northwest, specifically another secession movement against the Union government--thereby, hopefully, the Union would sue for peace to prevent a further breakup.
        Thompson accepted the challenge and was joined in Canada by Clement Clay, an ex-senator from Alabama, who was given the title of Commissioner of the North. The action officers assigned to the effort were James P. Holcombe, a University of Virginia law professor, and Captain Thomas Henry Hines, a veteran Confederate spy (even though he was only in his early twenties).
        Why go to Toronto? By 1864, Toronto was much like Lisbon during the Second World War. Everyone had spies there and it was not infrequent that the spies traded information. In addition, C.L. Vallandingham, who was the Grand Commander of the Sons of Liberty and an outspoken sympathizer for the Confederacy, had fled from the U.S. to Canada in 1863. He purposed to detach the states of Illinois, Indiana and Ohio from the Union, if the Confederacy would move sufficient troops into Kentucky and Missouri to ensure their entry into the new Confederacy. Vallandingham wanted to form the five states into a new Northwestern Confederacy and thereby break the Union into three distinct pieces. He felt this action would force the Union to sue for peace. It is for all of these reasons that President Davis sent his powerful delegation north to Canada in the spring of 1864.
        Hines and his fellow agents did work closely with all of the Copperhead organizations in the Northwest, mainly the Knights of the Golden Circle, the Order of the American Knights, and the Sons of Liberty, in attempts to create uprisings. All that resulted from this liaison was a great deal of inflammatory talk and no action. It appears that Captain Hines, in his youthful optimism, often misread the rhetoric as a guarantee of action--action that never came to fruition.
        The following chronology summarizes the action undertaken by the Toronto operation:

    During May, June and July of 1864 Maine coastal residents noticed artists sketching along the shore. These artists, about 50 in number, were in reality Confederate topographers sent to Maine to map the coastline. They were looking for coves and inlets that could be used by armed steamers in a joint land and sea attack on Maine. The full attack never took place, again stymied by Union actions, and their scaled down attempt met with disaster. On July 14, 1864, the governor of Maine, Samuel Cony, received a telegram from the U.S. Consul in St. John, New Brunswick, Canada. The telegram warned Governor Cony that a Confederate party of 14 men was planning to land on the Maine coast. A later telegram stated the team was headed for Calais, in Maine, to rob a bank. It further stated the team was led by a man named William Collins.
    On July 18, 1864, the man named William Collins and two other men, Phillips and the famous Confederate courier Francis Jones, were captured on the Main Street of Calais walking towards the bank. When arrested and searched, a Confederate flag was found on Collins and he openly stated he was a Confederate, claiming to be a captain in the 15th Mississippi Infantry Regiment. No trace could be found of the other reported 11 men.
    No real connection could be found between the intended robbers and the Confederacy in Richmond or the operation in Toronto, and therefore the men were tried merely for "conspiracy to rob." Each was sentenced to three years in the Maine State Prison.
    Francis Jones, a disenchanted Confederate, confessed not only to his part in the Maine plot but also supplied information regarding Confederate weapons caches in the North as well as the names of 20 key Confederate agents operating in the Union. The operatives were in Maine, Massachusetts, New York, Pennsylvania, Maryland, Illinois, Mississippi, Kentucky, Tennessee and Ohio. Based on the disclosure mass arrests were made and weapons confiscated.
    In early June of 1864, Captain Hines planned an uprising in the Northwest timed with a raid by General John Morgans raiders in the Ohio/Kentucky area. General Morgan commenced a raiding mission in Kentucky on the 11th of June and was successful until he met the forces of General Burbridge who drove him out of the area and into Virginia. The raid did not create the desired unrest in the Northwest states.
An uprising was planned for August 29, 1864, timed with the Democratic Convention in Chicago. While the planning was extensive and assurances were given--no actual uprising occurred in Chicago as planned. President Davis comment after the failure of the mission was that the Copperheads did not do well as they had no military leaders.
    Political methods were also attempted. The Toronto operation funded the campaign of Democrat James C. Robinson for governor of Illinois. They were led to believe that if elected Robinson would turn over the states militia and arsenal to the Sons of Liberty. He lost the election.
    In the fall of 1864, operatives from Toronto did go to St. Louis, Missouri, to destroy the Union transports used to ferry Union troops and supplies on the Mississippi. They intended to use an inflammatory known as "Greek fire" (a Molotov cocktail), which was only successful about 50 percent of the time. The group did in fact manage to destroy or damage 5 to 10 of the 75 Union transports in port.
    In need of money, the Toronto operation staged a robbery in St. Albans, Vermont, in mid-October of 1864. The robbery was successful and the agents returned with over $200,000 in gold and U.S. currency. (When pressed by the U.S. for the return of the bank robbers, Canada refused since they were able to prove they were on a military mission--they produced their orders from Richmond).
    Uprisings were next planned in Chicago, New York, Boston, Cincinnati and other locations for Election Day, November 8, 1864. The operation in Canada supplied the money and weapons to make the uprisings happen--but to no avail.
    On November 25, 1864, Confederate operatives from Toronto came to New York City with the intention of "flaming" the city. They selected 19 hotels as targets and hoped to create a riot similar to the New York City draft riots. While some of the hotels did in fact sustain fires, in several cases the Greek fire did not ignite and the total effect was not what was desired. All of the operatives did manage to escape from the city which was a neat trick since a double agent, Godfrey Hyams, had informed the Union of the threat to New York.
    The next target was the USS Michigan, the only gun ship on the Great Lakes. The attempt, made on December 19, 1864, was abortive due to a Union counter spy, J. Winslow Ayer, placed in the Confederate prison camp on Lake Michigan as a patent medicine salesman. He heard the Confederate prisoners talking about the fact that when the ship was taken over they were to rise up, take over the camp and then depart on the steamer.
    In December of 1864 Confederate operatives working for Hines decided to kidnap Vice President-elect Andrew Johnson on his way to Washington for the inaugural. They had a specific plan to capture him in his hotel room in Louisville, Kentucky, and take him away in a covered coach. The first night they attempted to execute the plan events made it impossible. On the second attempt, the agents rushed into the vice presidential suite all too easily, then found that the official party had left about an hour earlier. Vice President Johnson had decided to continue on his journey by boat instead of train.
    After the war, at the Lincoln assassination trial, a witness testified that the Toronto operation actually attempted "pestilence warfare" late in the war. The effort was reported to involve the delivery of "Yellow fever infected" blankets and clothing to Washington, D.C., in hopes of infecting the President and his cabinet with the disease.

        The Union was well aware of the threat represented by the actions of both C.L. Vallandingham and the Toronto operation and a major effort was made to infiltrate one of the Copperhead organizations to avert surprise. They were very successful in this endeavor in the person of Felix Stidger. Stidger was a Midwesterner by birth and was very familiar with Indiana, Kentucky and Ohio. He was a Union soldier under the command of Brigadier General Henry Carrington, who headed the intelligence operations in Indiana. On orders from Carrington, Stidger successfully infiltrated the Knights of the Golden Circle in Indiana in early 1864 and over time rose to the rank of Secretary General of the Grand Council of Indiana. Until October of 1864 Stidger submitted continual reports on the activities of the Knights of the Golden Circle and their involvement with the Toronto Confederate group to General Carrington. In October of 1864, Stidger along with over 100 of the Knights of the Golden Circle hierarchy were arrested. The Knights did not realize that Stidger was a Union agent until he appeared to testify against them.
        All in all, it is estimated that the Confederacy spent over a million dollars funding their efforts to get the Copperheads to rise up, all to no avail due largely to Captain Hines. He was a young idealistic officer who believed that everyone with whom he had contact had the same genuine enthusiasm for the cause that he did. Therefore his reports back to Thompson in Toronto were glowing and full of guarantees that all was well and indeed moving the way the Confederacy wanted it to go. The operation finances could well have been used by the Confederacy for many other purposes, however, in his desperation President Davis felt an uprising had a chance and he refused to let his hopes die.
        The overall failure of the Toronto operation was not only the fault of Captain Hines; it was also due to the excellent counter-espionage efforts of the Union. By this late stage of the War the Union had a very sophisticated counter-espionage organization that had great successes--due in no small part to the lack of appreciation of their work by the Confederacy. While the Union began the war well behind the Confederacy in the world of espionage and counter-espionage, by the final stages the situation was completely reversed.

Source: "Spies and Spymasters of the Civil War" by Donald E. Markle

This Page Last Updated:  02/10/07