PROLOGUE:

'ABE’S CONTRACT WAS UP'

Mint juleps were available year-round in Dooley’s Bar at the swank St. Lawrence Hall in Montreal. The libations were served just the way the Southerners from the Confederate States of America liked them: mint leaf, bourbon, some simple syrup and crushed ice, cold enough toallow a thin frost to caress the outside of the cup.

When the handsome Southern gentleman walked into the popular hotel bar on St. James Street one evening in October 1864, many of the patrons would have recognized him. Dark, curly hair, piercing eyes, an easy smile and the confident walk that came from being an actor of considerable renown—“A Star of the First Magnitude,” as one glowing tribute had put it; “a muscular, perfect man,” gushed another.

In the previous months, John Wilkes Booth had starred in performances in Nashville, Cincinnati, New Orleans and Boston. But in Montreal, he stayed away from the stage; he told people he was in town on “a pleasure trip,” though in truth he would spend a lot of time conducting serious business with Confederate agents and sympathizers who flooded the city.

Perhaps the only person at Dooley’s who was as well-known as Booth—at least to the locals—was the stocky man with the neat brown hair who was standing by the pool table in the billiards room next door to the bar. Joseph Dion sported a handlebar moustache that drooped below his chin and seemed to come all the way up to his ears. The Quebec billiards champion was enough of a celebrity to have his picture on a cigarette trading card.

“I was introduced to J. Wilkes Booth,” Dion later recalled, “and indulged in a friendly contest of billiards with him in the saloon of that establishment which was to continue to a late hour in the evening.”

There is no record of whether Dion was polite enough to let his American guest win. But it was the conversation rather than the competition that the billiards champion distinctly remembered about Booth. More specifically, “the wild ideas he expressed.”

“Do you know, I have the sharpest play laid out ever done in America,” Booth boasted. “I can bag the biggest game . . . just remember my address, you’ll hear of a double carom one of these days,” ostensibly referring to the rare pool trick of sinking two balls at once.

As the game and the evening wore on, Booth seemed to get more inebriated—and more political. The American elections were just a few weeks away; Abraham Lincoln’s political future—and the uncertain future of his divided country—hung in the balance as the President fought for re-election.

For three years, Lincoln had been waging a war against the slave-holding Southern states that had broken away from the Union. His Emancipation Proclamation of January 1863, declaring “that all persons held as slaves” within the rebellious states should be free divided the country even more.

Booth, like most Confederate supporters, despised Lincoln—and made his views clear to his Canadian host. Many months later, when his words took on a much more ominous meaning, Dion recalled Booth saying that “it made damned little difference, head or tail, Abe’s contract was nearly up.”

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It was no accident that the man who would become the world’s most famous assassin found himself in Dooley’s Bar just six months before he pointed his single-shot, .44-calibre derringer into the back of Abraham Lincoln’s head.

In Montreal, Booth was among friends. The St. Lawrence Hall wasa notorious hangout for Confederate spies in a city that was a hub for wartime plotters, assassins, mercenaries and soldiers on the run. A few hours’ journey down a dirt highway or by slow train, Toronto was also a headquarters for Confederate money men and gunrunners. Canada in the 1860s was a country rife with espionage, a secret northern frontin a civil war that was tearing apart its neighbour to the south.

By early 1864, Jefferson Davis, the leader of the Confederate States, would order some of his most trusted aides to “proceed at once to Canada” to set up a well-funded secret service network. The Lincoln administration in turn sent its detectives and entice snitches to Canada to spy on the spies.

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Today, Canadians take pride in having been on the “good side” in the battle against slavery, a refuge for thirty thousand Black men, women and children who fled to what they would call the “North Star” of freedom on the Underground Railroad. That heroic endeavour is only part of the story. Much less talked about is Canada’s own history of racism, and the complicated role Canada played in the Civil War.

The truth is that not all Canadians were cheerleaders for “Honest Abe” in his fight against the rebel slave states. In fact, with support from powerful men in the ruling elites, the country provided a staging ground for Confederate kidnap plots, fire bombings, bank raids and prison breaks. Shortly after Lincoln’s assassination, Washington issued a formal proclamation explicitly declaring that “the atrocious murder”of the President was “incited, concerted and procured by . . . rebelsand traitors against the government of the United States harbored in Canada.” Five of the six alleged conspirators named in the indictmentwere operating out of Montreal and Toronto.

The sixth man, Jefferson Davis, was still in America. He was imprisoned after the defeat of his Confederate army, but once released on bail, Davis immediately fled to where many of his Confederate compatriots had already found refuge: Canada. He received a hero’s welcome.

The echoes of the war to end slavery still linger today, in both America and Canada.

Many books about the Civil War focus mainly on the powerful politicians and generals, inevitably all men. The North Star, however, is about ordinary people who chose a life-altering path as they stood at history’s crossroads. Some choices were made for them by their circumstances: the place of their birth, their class and social standing, their gender, their religion and the colour of their skin. But at key moments in their lives, each made critical decisions. Some changed careers, some changed countries; one of them managed, in a way, to change her gender.

Their choices would have extraordinary outcomes none of them could have envisaged when they took those first fateful steps. A farmgirl from New Brunswick, disguised as a man, would fight in some of the bloodiest battles of the war as a Union soldier. A young Black man in Toronto whose parents fled slavery and racism in Alabama would become the first Canadian-born Black doctor, and would find himself at the Washington home where Lincoln lay dying from an assassin’s bullet. A prominent and wealthy Toronto aristocrat would open his heart, his wallet and his home to the Confederate Secret Service leaders in Canada.

And a boy who grew up in a small village outside Montreal would become a respected lieutenant in a Washington cavalry regiment. Immediately after the assassin’s bullet was fired at Ford’s Theatre, he was tasked with leading the most famous manhunt in American history.

His prey would be the billiard player John Wilkes Booth, whose own choices would change the course of history.