Historicist: Confederates and Conspirators
Torontoist has been acquired by Daily Hive Toronto - Your City. Now. Click here to learn more.




Historicist: Confederates and Conspirators

There were many Canadian fans and supporters of the Southern cause in the U.S. Civil War.

Every Saturday at noon, Historicist looks back at the events, places, and characters—good and bad—that have shaped Toronto into the city we know today.

Queen’s Hotel, 1908. City of Toronto Archives, Fonds 1244, Item 333.

When Jacob Thompson arrived in Toronto at the peak of the hostilities of the U.S. Civil War, in the early summer of 1864, the city was already a hotbed of espionage and counter-espionage. The prosperous lawyer and businessman from Oxford, Mississippi, had been a member of the United States Congress and Secretary of the Interior under President Buchanan. Now, he’d arrived in Toronto at the behest of Jefferson Davis, president of the Confederate States of America, on a well-funded mission to coordinate subversive activities against the North from the British North American colonies.

Thompson checked into the Queen’s Hotel, the luxurious hotel located on Front Street overlooking the lake. The Queen’s Hotel was—along with Toronto’s American Hotel—one of the preeminent locales in British North America, Robin W. Winks writes in Canada and the United States: The Civil War Years 4th edition (McGill-Queen’s University Press, 1998), where “the Confederates established informal headquarters where they slept, drank, gathered to curse the North and to plot raids, and waited for someone with authority to show up to lead them.”

With more than 100 Southerners renting out the entire hotel, residents included both aristocratic refugees and fugitive soldiers who’d escaped Northern prison camps. James D. Horan described the scene in Confederate Agent (Crown Publishers, 1954):

There was no mistaking the escaped Rebel prisoners. They hung around the lobby and bar of the Queen’s, trying to appear respectable in torn gray coats and cracked jackboots or in castoff clothes they had robbed from some clothesline after climbing the board fences of Camps Chase, Morton, or Johnson’s Island. They were gaunt, hollow-eyed men, with faces lined and tanned the color of old leather by the relentless sun which had scorched the treeless prison yards that rainless summer.

Southern agents operated freely and openly with little to no concern from local authorities who were governed by British North America’s official policy of neutrality. Indeed, Southerners enjoyed the sympathy of most of Toronto’s political, social, and business elite—although few were as enthusiastic in supporting the Confederate cause as George Taylor Denison III.

Portrait of Jacob Thompson, 1857, via Wikimedia Commons.

As Eric Jarvis details in his contribution to Celebrating One Thousand Years of Ontario’s History (Ontario Historical Society, 2000), “the American Civil War became something of a spectator sport for many Torontonians. There was a vicarious interest in the events of the war and the fascination associated with a dramatic and violent spectacle.” Despite the efforts of George Brown’s Globe newspaper to keep the public focused on slavery as the cause of the American conflict, the majority of Canadian newspaper readers held anti-Northern sentiment. At one point in 1861, a uniformed Union soldier visiting Toronto was loudly jeered by passersby and was greeted, upon entering a saloon, by the musical accompaniment of “Dixie.”

Although most British North American citizens did not favour slavery, they feared that the North was only interested in conquest and that, if the South were vanquished, annexation of British North America would be next. Denison—who would later serve as the city’s police magistrate—was among those who raised the spectre of imminent annexation in a polemic he published, calling for British North American defences to be raised.

Moreover, Southerners who frequently vacationed in the Niagara region before the war had forged close ties with the local elite in Canada West. While visitors from the Northern states were perceived as unscrupulous businessmen and crass nouveau riche, the wealthy and refined tourists from the South convinced many in Southern Ontario “of the righteousness of their cause”—as Winks put it.

Denison’s father’s residence, Rusholme, July 3, 1923. Heydon Villa was similar but grander. City of Toronto Archives, Fonds 1266, Item 1023.

The Denison family of Toronto was prime among those who felt a kinship with the Southern gentry. When George Taylor Denison III built a baronial house at the southwest corner of (present-day) Dovercourt and College in 1864, he self-consciously styled it upon Southern mansions. Heydon Villa—as he christened it—was surrounded by elegant gardens and a forest, and featured “a wide veranda supported by Doric columns, a Grecian pedimented entry, shuttered windows, and eighteen-foot ceilings.”

As Norman Knowles argues in the Dictionary of Canadian Biography, Denison’s “identification with the South came naturally: it represented an idyllic society that embodied the social order, conservative values, and chivalric traditions he wished to see maintained in British North America. He drew parallels between his loyalist ancestors, who had fought to uphold their principles against the demagoguery of American patriots, and the southerners, who were struggling to preserve their identity and way of life.”

By the time Thompson arrived in Toronto to take charge, illicit activities on behalf of the Confederacy were already underway—and had been since the war’s commencement. “An efficient Southern agent,” Winks writes, “could learn with comparative ease of troop movements, gun emplacements, or diplomatic squabbles” but had no means of rapidly communicating the information to the Confederate States. But the vast—and largely unguarded—border made it difficult for the Union to intercept messages. Couriers, Winks notes, “traveled across Lake Ontario from Toronto or Hamilton on grain boats headed for ports in New York or slipped across the St. Lawrence River at night….During the summer hundreds of skiffs passed up and down the river, making it difficult to detect an irregular river crossing.” Therefore, the Union sent its own agents across the border to man observation posts. Initially, British North America authorities made little effort to impede either side in deference to the colonies’ stated neutrality.

Portrait of Thomas H. Hines, 1884, from John W. Headley, Confederate Operations in Canada and New York (Neale, 1906).

“Agents of the Confederacy,” Horan writes, “and detectives for the Union, [walked] in and out of the Queen’s bar, buying, selling and trading information, much of it worthless, from the freelance agents who had run the land route via the Detroit ferry to Windsor or the sea blockade from Wilmington to Bermuda, then to Canada.”

Although Montreal and Windsor were also hot beds of Confederate activity, the epicentre of such activities in Toronto was the Queen’s Hotel. Thompson headquartered there, Adam Mayers writes in Dixie & The Dominion (Dundurn, 2003), because “it suited his taste for fine living. Its foods, wines, and service were renowned, and the main floor telegraph office offered instant communication with allies and emissaries. The hotel carried the latest American newspapers, whose classified ads were another of Thompson’s forms of communication with Richmond.” At its liveliest, Horan writes, the Queen’s Hotel resounded “with the crash of broken glasses and the voices roaring out the words of ‘Morgan and Duke Ride Tonight'” and other whiskey-fuelled sing-alongs.

It was in this atmosphere that Thompson and his many affiliates hatched and executed a variety of plots against the North. Captain Thomas H. Hines, a young Kentuckian with a reputation for daring deeds, had been sent to Canada to organize escaped prisoners and the like into a force which could free soldiers incarcerated in Northern prison camps. He also attempted to foment an insurrection in the states of Illinois, Indiana, and Ohio—timed to coincide with the August 29, 1864, Democratic Convention in Chicago—but failed because in his idealistic naivety, he overestimated the resolve of others.

On November 25, 1864, a group from Toronto firebombed selected targets in New York City with Greek Fire—a molotov cocktail made from sulphur, naptha, and quicklime. Despite some wreaking some havoc, little damage was done because the attackers had been betrayed by a double-agent.

Another scheme late that year was to capture the Union’s only gun ship on the Great Lakes, the U.S.S. Michigan. In December 1864, an attempt by Hines and others to kidnap Vice-President-Elect Andrew Johnson was foiled.

Another plotter was George N. Sanders, an ebullient former consul in London for the President Franklin Pierce administration. A constant presence at the Queen’s Hotel—always unkempt and disheveled—Sanders belligerently pestered his colleagues that robbing banks in Northern cities was an act of war. A raid along those lines, attacking St. Albans, Vermont, was eventually carried out and helped turn public opinion north of the border against the Confederates.

Postcard of the Queen’s Hotel, 1910, from the Toronto Public Library.

Life wasn’t all intrigue for those exiled in Toronto. In his memoirs, Confederate Operations in Canada and New York (Neale, 1906), John W. Headley recalled an afternoon spent in a skiff on the lake with a fellow soldier:

The city presented a grand front when viewed from a distance out in the bay. There was everything in the prospect at Toronto to make a sojourn enjoyable. The leading newspapers of Canada were published here and the South got a friendly comment on the course of events. All the news of the war and from the front of the armies was published daily. We also received the New York, Chicago, Buffalo and Detroit papers.

Although Denison had long been sympathetic to the Southern cause, his involvement heightened with the arrival of his uncle, George Dewson, from Florida in September 1864. A colonel in the Confederate Army, Dewson had been sent by the Confederate cabinet “to evaluate and report on Jacob Thompson’s activities,” according to Mayers. “Dewson’s presence at Heydon Villa and Rusholme was an invitation to any and all Confederate sympathizers and agents to come calling.” Frequent guests included Thompson and Confederate sympathizers like W. Larry Macdonald, who operated an explosives factory in Toronto.

“I became very friendly with Colonel Thompson,” Denison recalled in his memoirs, Soldiering in Canada (Macmillan and Co., 1900), “and he used to visit at my house. I was a strong friend of the Southern refugees who were exiled in our country, and I treated them with the hospitality due to unfortunate strangers driven from their homes.” Both during and after the war—when his guests would include General W.C.P. Breckenridge, General Jubal A. Early and other high-ranking members of the Confederate Army—Denison argued that his interest in Confederate guests was purely to learn from their military expertise. However, despite the prevalence of Southern sympathizers in British North America, few prominent citizens were as unconcealed or zealous in their support of Southern secret service operations as Denison.

By the fall of 1864, Thompson’s activities had attracted a growing amount of counter-espionage. In the hotel bar—and across the street at the railway station—Union detectives observed the comings and goings of Confederate spies and agents. “The bane and curse of carrying out anything in this country,” Thompson lamented in a letter, “is the surveillance under which we act. Detectives or those ready to give information stand at every corner. Two or three cannot interchange ideas without a reporter.”

Portrait of John Yates Beall, another Southern spy in Toronto, 1864, from John W. Headley, Confederate Operations in Canada and New York (Neale, 1906).

With more and more couriers being caught, it was getting more and more difficult for Thompson to communicate with his superiors in Richmond. He turned to Denison for help. For a number of days in early January 1865, Lieutenant Sam Davis, a fair-haired 20-year-old Confederate courier—who’d been injured in combat at Gettysburg—hid at Heydon Villa. “He kept in the house and only went out for exercise after dark,” Denison recalled in Soldiering. When Thompson was ready to send Davis south, the former Congressman slipped out of his hotel undetected after dark, and went to Denison’s to issue final instructions.

Denison knew that Union had learned all the spy tricks employed by Confederate agents. “Boots and collars were cut open and folds of cloth everywhere examined,” he wrote in his memoirs. “Buttons were taken to pieces and carefully scanned under magnifying glasses.” In Soldiering, Denison boasted that he pitched a new technique to Thompson. He suggested that the secret messages be written on white silk, and stitched into the elbows and the lining of the coat—undetectable to the touch. Thompson approved and Denison’s wife, Caroline, was enlisted to do the sewing.

In the pre-dawn hours, Denison guided the young spy to Mimico station to catch his southbound train. Once Davis was across the border, however, he was recognized and arrested in Newark, Ohio. Although his dispatches weren’t discovered—thanks to Denison’s innovation—he was tried as a spy at Cincinnati and sentenced to death (although the sentence was eventually commuted on President Lincoln’s order).

Denison was also involved in a scheme to buy a steamer ship to be armed for raids on the Union. Thompson, through a number of middle-men that included Denison, acquired the Georgian for $17,000—well more than the vessel was worth. Dismayed at the growing derision with which Confederates treated British North America’s neutrality, Canadian authorities made a point of pursuing the Georgian affair with some zeal. In the version of events recorded by Winks, British North American revenue collectors inspected and harassed the Georgian and her crew each time the vessel put into port. Despite Denison’s claims that the Georgian was to be used in the lumber trade, the vessel was eventually impounded in Collingwood. Furthermore, authorities carried an investigation of Denison’s role in the transaction beyond the end of the Civil War, eventually putting him on trial for violating neutrality. He was acquitted and tried to sue the government for damages.

As the Civil War progressed, Winks argues, the St. Albans raid, the Georgian affair, and other incidents “turned many formerly pro-Southern Canadians against the South. A noticeable shift in public opinion coincided with a noticeable shift in official attitude.” During his year in Toronto, Thompson oversaw a litany of failures. The only notable success for the Confederates in Canada was the St. Albans raid (which Thompson doesn’t appear to have sanctioned in advance) that helped turn public opinion in British North America against the South.

Daguerreotype of Jefferson Davis, 1853, via Wikimedia Commons.

In a March 1921 article in the Canadian Historical Review (Vol.2, No.1), Wilfrid Bovey provided his assessment of Thompson and other Confederates in Canada:

[They] had plotted a great deal, spent an enormous amount of money, caused the death of a number of innocent people and of some of their own misguided subordinates, and accomplished absolutely nothing. Sometimes they had chosen their assistants badly; once or twice luck had been against them; but the greatest of their errors was that they entirely misjudged the spirit of the people they were fighting.

Eventually relieved of his post, Thompson bounced around in exile for a number of years before eventually settling in Memphis, Tennessee, where he died in 1885.
For the remainder of his life, Denison was unrepentant about his Confederate sympathies. In April 1865, as an alderman for St. Patrick’s Ward, he was the only voice of dissent when Toronto’s council passed a motion expressing sympathy for the United States over Lincoln’s assassination. On May 30, 1867, Jefferson Davis passed through Toronto on his way to a recuperative holiday in Niagara after two years of imprisonment. Denison spread word of the former Confederate president’s imminent arrival. He helped gather a crowd of almost 7,000, and upon the arrival of the steamer Champion, he scrambled to the top of a coal heap to lead the crowd’s huzzahs. As late as 1916, Denison even ventured to the American South to be feted at a reunion of Confederate veterans in Birmingham, Alabama.

For others, however, British North America’s sympathetic conduct towards the unpalatable Southern cause proved to be an embarrassment best forgotten. And in the Dictionary of Canadian Biography, Knowles asserts that Denison’s open and active support for the Confederacy cost him the Canadian military and political leadership to which he so greatly aspired—and which he felt was his due.

Others sources consulted: Tom Brooks and Robert Trueman, Anxious For A Little War (WWEC, 1993); David Gagan, “The Historical Identity of the Denison Family of Toronto, 1792-1860,” Historical Papers (Vol.6, No.1; 1971; Claire Hoy, Canadians in the Civil War (McArthur & Company, 2004); Oscar A. Kinchen, Confederate Operations in Canada and the North (Christopher Publishing House, 1970); and Donald E. Markle, Spies and Spymasters of the Civil War (Hippocrene Books, 2000).

UPDATED August 16, 2017 at 12:51 p.m. to include a deck/subtitle.