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Canada in the Civil War

When we think of the Civil War we rarely even think of Canada but our Canadian neighbors played a significant role in the war. Early on in the war Canada provided a safe haven for Confederate prisoners of war who escaped from Northern prison camps and also served as a relay point for communications between England and the Confederacy.

In 1863, C.L. Vallandingham, an outspoken Confederate sympathizer, fled to Canada in the hopes that he would be able to convince the states of Illinois, Indiana and Ohio to secede from the Union. He wanted to form a Northwestern confederacy which would break the Union into three distinct pieces and hopefully cause the Union to seek peace.

By 1864, Toronto hosted spies from all sides. The fact that they often traded information made the city a most likely place from which to launch a secret operation creating hostile activities in the Northwest just as Vallandingham had wanted to do. Jefferson Davis sent Jacob Thompson a telegram on April 7 stating "If your engagements permit you to accept service abroad for the next six months, please come here immediately." Thompson a staunch supporter of the Confederate cause responded quickly and accepted the challenge. Joined by Clement Clay of Alabama, James Holcombe of Virginia and Captain Thomas Hines, a young veteran Confederate spy, he left for Canada in the Spring of 1864.

The following is a chronology of the actions of the Toronto operation:

--During May, June and July of 1864 Maine coastal residents noticed artists sketching along the shore. These artists were actually topographers who were mapping the coastline. They were looking for coves and inlets that armed steamers could use in a joint land and sea attack on Maine. A smaller than planned attack was turned back by Union actions

--On July 14, the U.S. Consul in St. John, New Brunswick, Canada sent a telegram to the governor of Maine warning him of a Confederate plan to land 14 men on the Maine coast. The governor later received a second telegram telling him of the plans of the landing party to rob a bank in Calais, Maine.

--On July 18, three of the men, William Collins, Phillips and Francis Jones, were captured on the Main Street of Calais walking towards the bank. Collins was found to be carrying a Confederate flag and openly stated that he was a Confederate, supposedly a captain in the 15th Mississippi Infantry Regiment. The other 11 men were not found. Because no real connection between the three men and Richmond could be established they were tried for "conspiracy to rob" and sentenced to three years in the Maine State Prison.

--Francis Jones, who was disillusioned with the Confederacy, confessed to his part in the plot as well as supplied information about Confederate weapons caches in the North. He also provided the names of 20 key Confederate agents operating in Maine, Massachusetts, New York, Pennsylvania, Maryland, Illinois, Mississippi, Kentucky, Tennessee and Ohio. Based on this information mass arrests were made and large stores of weapons confiscated.

--In early June 1864, an uprising planned for the Northwest was timed with a raid in the Ohio/Kentucky area. The mission in Kentucky was successful until the Confederate forces were driven out of the area and into Virginia. This plan did not create the desired effect in the Northwest states.

--An uprising planned to be timed with the Democratic Convention in Chicago on August 29, 1864 also failed.

--The Toronto operation funded James Robinson's campaign for governor of Illinois. They believed that if elected Robinson would turn over the state's militia and arsenal to the Sons of Liberty, one of the Copperhead organizations in the Northwest. He was not elected.

--In the fall of 1864, operatives left Toronto for St. Louis, Missouri, to destroy Union transports used to ferry Union troops and supplies on the Mississippi. They managed to destroy or damage 5 to 10 of the 75 transports in port.

--Because the operation needed money they staged a robbery in St. Albans, Vermont in October of 1864. This time the robbery proved to be successful and the agents returned to Toronto with over $200,000 in gold and U.S. currency. Canada refused to return the money to the U.S. because they were able to prove they were on a military mission by providing their orders from Richmond.

--The Toronto operation provided money and weapons for uprisings in Chicago, New York, Boston Cincinnati for Election Day, November 8, 1864 but the uprisings never happened.

--On November 25, 1864, operatives went to New York City aiming to create a riot and set the city on fire. Some of the hotels sustained fires but again the effect was not what was desired.

--Operatives next targeted the USS Michigan, the only gun ship on the Great Lakes. Confederate prisoners in the prison camp on Lake Michigan were to rise up, take over the camp and escape on the steamer when it was overtaken. However the plan was aborted because a Union counter spy in the camp overheard the prisoners talking and reported what he heard.

--The operatives attempted one last operation in December of 1864. They planned to kidnap Vice President-elect Andrew Johnson on his way to Washington for the inaugural. Events prevented them from taking him in his hotel room in Louisville, Kentucky and their second attempt also met with failure. When they rushed into the vice presidential suite they found it empty. Johnson left earlier after deciding to continue the journey by boat instead of train.

A witness at the Lincoln assassination trial testified the Toronto operation attempted "pestilence warfare" late in the war. Supposedly, "Yellow fever infected" blankets and clothing were delivered to Washington, D.C. in the hopes that the President and his cabinet would be infected.

The Toronto operation failed in part because of Captain Hines idealism. He believed that everyone had the same enthusiasm for the cause that he did. Therefore, his reports to Thompson in Toronto were full of optimism and guarantees that all was well and things were going well. But the Union at this stage of the war had a very sophisticated and successful counter-espionage organization that stopped the Confederacy dead in their tracks.

Sources for the tidbit this week is

Spies & Spymasters of the Civil War, Donald E. Markle. Copyright 1994 Donald E. Markle; Hippocrene paperback edition, 1995

© 2006 Winifred Ledoux