The May 1, 2025 meeting of The Civil War Round Table of Greater Kingston featured a presentation by member Brent Holland on what is perhaps one of the lesser-known aspects of Canada's involvement in the American Civil War. When we think of Canada and the Civil War, we tend to recall such things as our participation in the Underground Railroad, which smuggled tens of thousands of escaped enslaved people from the United States into Canada West. Or we may think of the approximately fifty thousand Canadians who enlisted in the Union army during the Civil War. We are less likely to be aware of Canada's role in providing a safe haven for Confederate agents gathering intelligence about the North, or those planning military operations against the Union war effort. Most notoriously, there is evidence that planning for the assassination of President Abraham Lincoln actually took place on Canadian soil.

Brent's interest in American history-and especially, the assassination of President John F. Kennedy-has been a part of his own YouTube channel, where you may find his videos under the title "nightfrightshow". The content Brent presented to us on this particular May 1st evening may be found in a fifty-minute video bearing the caption, "Lincoln assassination plot John Wilkes Booth & Canada Julian Sher Paul Van Nest Brent Holland Show". What follows is a summary of the discussion contained in that video.

Brent began by introducing his guests for the evening. First, there was award-winning Canadian journalist, Julian Sher, author of the book, "The North Star: Canada and the Civil War Plots Against Lincoln", published in 2023. Also joining the discussion was our own Paul Van Nest, a man who has been known to politely correct U.S. National Park Service Rangers when they give erroneous information to their Civil War battlefield tour groups.

To set the scene, Brent asked us to imagine the tall handsome figure of the famous actor, John Wilkes Booth, pool cue in his hand, having a friendly game of billiards in Dooley's Bar at the St. Lawrence Hall on St. James Street, Montreal, the most luxurious hotel in all of British North America, set in the heart of Canada's financial district. It is October of 1864, and 591 miles to the south of where Booth is standing, Abraham Lincoln is in the middle of his campaign to win a second term for the Presidency of the United States. The Civil War is not going well for the Richmond government, and the Maryland-born Booth is among those Confederate sympathizers seeking a way to redress the fortunes of war in favour of the South.

Julian then outlined the plan Booth had devised in the summer of 1864 to kidnap President Lincoln and hold him for ransom in exchange for the release of the thousands of Confederate p.o.w.s being held in Northern military camps and prisons. This is the plan Booth and his small band of accomplices attempt to carry out in March of 1865 after his return to Washington, D.C.. But the plan goes awry when Lincoln's carriage follows an unexpected route, and Booth decides his only recourse is to murder the newly- elected President.

As Julian described, Booth and hundreds of other Confederate agents were able to operate quite openly in Montreal, Toronto, and other parts of British North America, as the British government had adopted a position of neutrality in the American Civil War. While staying in Montreal in October of 1864, Booth read newspaper accounts of the St. Albans Raid that took place on the 19th of the month. A group of Confederates based in Canada East rode south to the Vermont town of St. Albans, where they robbed several banks before escaping north to safety across the border.

Speaking of banks, Julian related how the Montreal Confederates held more than $650,000 (about ten to twelve million dollars in today's valuation) at a branch of the Ontario Bank, where Booth did his banking as well. In fact, after Booth was tracked down and killed twelve days after Lincoln's assassination, a bank draft for $300 from the Ontario Bank was one of the items found in his pockets. Incidentally, Julian mentioned that the man in charge of the Union army detachment that hunted down Booth was Lieutenant Edward Doherty, a native Montrealer. Paul then mentioned that it was a Canadian from the New Market, Ontario, region who mortally wounded Confederate General Jeb Stuart at the Battle of Yellow Tavern in May 1864.

One of the points Julian wanted to emphasize was that Canadians of the Civil War era were not necessarily as pro-Union and anti-Confederate as we would like to think. After the assassination of Lincoln in April 1865, newspapers such as the "Monreal Gazette" lamented the President's death, while simultaneously suggesting that his murder was perhaps justified by what the paper called his despotic actions in putting down the Southern rebellion. Of note, this newspaper was founded by Benjamin Franklin in 1776 during his sojourn in Montreal as part of a diplomatic mission from the American rebels to the 14th colony. [Ed. Is there a little dig in there?]

There was also the warm welcome given to former Confederate President Jefferson Davis by the citizens of Montreal when he and his wife, Varina, came to visit in 1867. This was following Davis's two years of imprisonment in the U.S. after the Civil War. Julian described the reception the Davis couple received when they attended a theatre performance one evening. The audience began to applaud, the orchestra struck up "Dixie", and shouts of "The South will rise again!" were heard. Such a thing wouldn't have happened in New York, Boston, or Chicago, said Julian, but it happened in Montreal. Davis was then invited to Toronto, where a cheering crowd of several thousand greeted him and his wife. This was followed by a tour of the Niagara Peninsula, which had become something of a Confederate Riviera for many former rebels, such as John C. Breckenridge, James Mason, and Jubal Early. Davis even gave a speech, in which he thanked Canada for having been "a haven for me and so many of our friends." As Julian observed, there is "a dark side" to Canada's history during the Civil War that has been hidden for too long. Although it is true that slavery was officially abolished in Canada and the rest of the British Empire in 1834, thirty years before the Emancipation Proclamation, that should not overshadow the fact that black Canadians suffered under slavery in our country, one prominent example being Marie-Joseph Angelique, tortured and executed in Montreal in 1734 after having been accused of arson in setting fire to part of the city.

The conversation then moved on to the participation of black Canadians in the Civil War, these being escaped enslaved people who had made their way north via the Underground Railway, free blacks who left the U.S. to live in Canada, and native-born black Canadians. Julian referred to Dr. Alexander Thomas Augusta, originally from Norfolk, Virginia, who moved to Toronto in the early 1850s to obtain the medical training denied him in the U.S. After becoming Canada's first black physician, Dr. Augusta later mentored a Canadian-born black medical student, Anderson Abbot, who likewise became a doctor. With the issuing of the Emancipation Proclamation in September 1862, both Dr. Augusta and Dr. Abbot wrote to President Lincoln offering their services to the Union army as medical officers, and both were accepted. The two became familiar figures at the White House, as well as at Washington's military hospitals and, after Lincoln's death, his widow, Mary Todd Lincoln, would give Dr. Abbott the shawl that Lincoln had worn at his second inaugural address as a token of the late President's esteem for the Canadian doctor.

Julian remarked on the bad habit of using presentism when assessing historical figures; that is, judging the thoughts and actions of people of the past by our present-day standards rather than their own. This, however, does not mean we should give Civil War era Canadians a free pass on their pro-South sympathies simply because such opinions were so prevalent at the time. Julian pointed to the example of George Brown, publisher of "The Globe" newspaper, who was quite outspoken in his denunciation of slavery. We should also remember the tens of thousands of Canadians who enlisted in the Union army to help defeat the Southern slaveholders. It's all a question of what choices people choose to make when confronted with the issues of their time.

Brent then asked Paul to comment upon Sir John A. Macdonald's attitude to the Civil War and his possible contacts with American politicians, North or South. Paul replied that he's never come across any evidence in his reading to suggest that Macdonald ever had any direct contacts with Lincoln or Davis. However, Macdonald was consumed by an interest in the Constitution of the United States and studied it closely for lessons it could teach him about the political organization he and the other Fathers of Confederation were attempting to craft for the then separate colonies of British North America. Macdonald came to the conclusion that the Civil War was the result of too many powers being defaulted to the individual states, and he resolved to found the Canadian Confederation upon the principle of a strong federal government. More specifically, the US Constitution permitted State governments to decide on issues not dealt with in the constitution; Macdonald held sway in the British North America Act that these powers be granted to the Federal government. There was also discussion of the strong motivation for Confederation arising from the threats from vengeful American politicians and generals to annex Canada in retaliation for complicity in the St. Albans Raid and other pro-Confederate activities. In recent months, we have heard similar annexation rhetoric from some voices in Washington.

At the end of the discussion, Brent asked Julian and Paul for a few final observations to offer to the young people who might be watching their video. Julian reminded the audience members that, as confusing and uncertain as our own times might be, they should draw strength and courage from the example of those young people who lived through-and in many cases, fought through-the American Civil War. Paul seconded this thought, and pointed out that, with the wealth of information available in books and online, it is possible to get to know the soldiers, generals, and political leaders of the Civil War on what seems like a personal level and be guided by their example. Finally, Julian reminded us that the Civil War has not really ended, that the same passions concerning race, states' rights, and regional cultural differences that inflamed Americans in the 1860s are still on full display on the American political scene today.

- edited by Tom Brzezicki