The Most Dangerous Woman in the World was playing a quiet game of cards. It was a snowy Toronto evening in the winter of 1940, that first terrible winter of the Second World War. She was staying with friends at their home on Vaughan Road, waiting for a meeting to begin. That’s when she slumped over in her chair. It was a stroke. One of the greatest orators of the twentieth century couldn’t speak a word.

This wasn’t the end most people would have expected for Emma Goldman. For decades now, she’d been the most notorious anarchist on earth. Her ideas made nations tremble: thoughts about freedom and free speech and free love; about feminism and marriage and birth control; about violence and pacifism and war. She’d been thrown out of the United States for those ideas, forced to flee Soviet Russia, driven out of Latvia, Sweden, Germany… Canada was one of the very few places where she was still relatively welcome. She spent decades in exile. And everywhere she went, she refused to be intimidated: giving fiery speeches, sparking riots, inspiring assassins, visiting war zones. Nothing could silence her. Not exile, not prison, not threats of violence. Nothing, that is, until that quiet game of cards.

The first stroke didn’t kill her. She still had a few weeks left to live, weakened and afraid, half-paralyzed, robbed of the powerful voice that had made her famous. But even on her deathbed, she had one more fight to win. There was one last life to save.

~~~

His name was Attilio Bortolotti. Some people knew him as Art Bartell. He was a leader of the Toronto anarchists.

Bortolotti was born in Italy in the very early 1900s — which meant that he was still just a boy when the First World War swept into his hometown. He saw terrible things: death and destruction raining down from the sky; dead bodies dumped in ditches; drunken soldiers killing their own men. But he also saw an act of kindness that would change his life.

One day, during an air raid, his young nephew was in danger of being crushed by falling debris. Bortolotti watched in amazement as a German officer — the enemy — threw himself over the young boy and saved his life. It was a shock. This wasn’t the image of the Germans the Italian newspapers were painting: of the inhuman, savage “Hun.”

“Young man,” the German officer explained to the confused teenager, “I want you to listen to what I have to say to you. I am a professor; I was teaching at the University of Berlin when I was called to serve in the army. I don’t feel that I have the right to kill you because you were born here; nor should you feel you can kill me because I was born in Berlin. I want you to remember three words: Freiheit über alles.” Freedom above all.

“A revolution,” Bortolotti later remembered, “began in my head.”

Once was the war was over, he left Italy for Canada. Here, he wouldn’t be forced into compulsory military service and could lead a more peaceful life. He was just sixteen years old when he sailed across the Atlantic, checking in at Ellis Island on his way north to join his brother in Windsor.

He spent the next few years working for a blacksmith and on construction sites and in auto factories — both in Windsor and just across the river in Detroit. But the life he found wasn’t entirely peaceful: the early 1900s were times of turmoil in North America, too — especially for the working class. These were the days of bloody union battles. Of police officers and soldiers killing striking workers in the streets. Of robber barons building private armies to crack down on dissent.

In Windsor, the young Bortolotti was exposed to new ideas. He spent long hours reading in the public library, talked about politics with his fellow workers, went to meetings, marched in protests and clashed with police. The more he learned, the more he saw, the more he became attracted to one idea in particular.

By then, anarchism was already an old idea: that government is inherently bad; that people should be completely free; that society should have no hierarchy at all. But in the last few decades, that old idea had been growing in popularity. Anarchists had played leading roles in some of the world’s most important events. In France, they helped to establish the Paris Commune. In Russia, they fought alongside the Bolsheviks as they overthrew the Tsar. In Canada and in the United States, they were on the front lines of the fight for labour rights: demanding reforms like an eight-hour workday.

But they were also growing ever-more notorious. While some anarchists didn’t believe in violence at all, those who did were giving the philosophy a reputation for bomb-throwing and assassinations. All over the Western World, anarchists were answering the violence against workers by trying to kill those in power.

They’d been doing it for decades. In Italy, King Umberto was shot three times in the chest as he climbed into his carriage. In Switzerland, Empress Elizabeth was stabbed to death with a file. In Spain, one Prime Minster was killed while relaxing at a spa and another while window-shopping at a bookstore in Madrid. In Kiev, the Russian Prime Minister was murdered during an opera. In Greece, King George was shot in the back while taking a walk. In the United States, President McKinley took two bullets to the stomach at point blank range while visiting the Pan American Exposition in Buffalo. Bombs blew up weddings and carriages and crowds, all in the name of anarchy.

Governments responded with arrests and executions and even more violence. Sometimes, it didn’t seem to matter who they were putting to death — guilty or not — just as long as they were anarchists.

One of the most infamous examples was the case of Sacco and Vanzetti. After a deadly armed robbery in Massachusetts, two Italian immigrants were arrested. They were both anarchists, they were both found guilty, and they were both sentenced to death. But they were also both innocent. The evidence in the case was so flimsy that it sparked international outrage, with major protests held in cities all over the world. In the end, Sacco and Vanzetti were both electrocuted anyway. It wasn’t until the 1980s that Massachusetts Governor Michael Dukakis finally cleared their names.

In Windsor, Attilio Bortolotti took up their cause. He organized meetings, raised money, and printed pamphlets. Even after the executions had been carried out, Bortolotti and his fellow anarchists continued to raise awareness of the case. Every year on the anniversary of the executions, you could find Bortolotti on the streets of Windsor and Detroit, handing out thousands of leaflets.

By now, his politics were starting to get him into trouble. His tireless opposition to fascism — which plenty of Canadians and Americans still supported back then, even as Mussolini marched on Rome and seized power in Italy — had gotten him blacklisted from jobs in the auto industry. His support for Sacco and Vanzetti earned him a meeting with Windsor’s chief of police, who told him he was no longer welcome in the city. He was ordered to leave town. At first, Bortolotti just moved across the river, but it quickly became clear that things were getting dangerous. He was arrested in Detroit for handing out pamphlets; the police, he said, beat him unconscious. When he made bail, he slipped back across the border into Windsor, and then kept right on running.

That’s how Attilio Bortolotti ended up in Toronto.

He got off the train at Union Station in the fall of 1929 — just a few weeks before the stock market crashed. At first, he didn’t know anyone in the city. But when he took his leaflets to an Italian neighbourhood on the anniversary of the Sacco and Vanzetti executions, he met a few Italian socialists and Communists who introduced him to another anarchist.

Before long they’d created their own Torontonian anarchist group: Il Gruppo Libertario. They published their own newspaper, organized meetings and events. They became familiar faces at the Labour Lyceum on Spadina Avenue: today, it’s a dim sum restaurant in Chinatown (on the corner of St. Andrew Street), but back then it was the political hub for textile workers in the heart of Toronto’s Jewish community. The Italians began to meet the city’s other anarchists: mostly Jewish and Eastern European immigrants. The community grew. Bortolotti had finally found his home.

It was only a matter of a time before he met another anarchist who had been staying in Toronto: the most infamous anarchist the world.

~~~

Emma Goldman was born in Russia in the late 1800s, back in the days of the Tsars. She grew up in what one of her biographers called “low-grade Tolstoyan unhappiness.” Her father beat her, sometimes with a whip, and when she turned twelve, he forced her to leave school and go work in a factory instead. “All a Jewish girl need know,” he told her, “is how to make gefilte fish, cut noodles fine, and give her husband babies.”

Still, even as a child, she was strong-willed and defiant. She had no patience for injustice. Decades before Bortolotti was shaped by the horrors of the First World War, Goldman was shaped by the horrors of Tsarist Russia.

“I was born a rebel,” she would later explain to the Toronto Daily Star, “but my first feeling of hatred for the present system came when I was six years old. At that time I saw a Russian peasant flogged and this sight of a human being degraded and tortured by his fiendish masters taught me that something was radically wrong somewhere. An indelible picture of the poor, suffering wretch has ever haunted my life.”

When she turned sixteen, her father demanded that she get married, so Goldman left home instead. Just like Bortolotti did at that very same age many years later, she sailed across the Atlantic, checked in at Ellis Island, and then headed north. She settled in Rochester, on the American shore of Lake Ontario, where her sister lived.

There, she fell in love with America: with its people and its relative freedoms. But that didn’t blind her to its flaws. Rochester was a city filled with sweatshops and slums. Workers toiled away over long hours in dangerous conditions for little pay. Goldman was still just a teenager, but she was bent over a sewing machine in a miserable factory for ten hours every day. It only got worse when her parents arrived from Russia. And when she did eventually get married, she discovered that her husband was impotent and depressed. She left him after only a few months.

Meanwhile, her political ideas were becoming ever-more radical. It was the Haymarket affair that finally turned her into an anarchist. The case had a lot in common with the trial of Sacco and Vanzetti. After a deadly bombing during a labour march in Chicago, the police arrested eight anarchists. All of them were convicted. Four of them were hanged. A fifth committed suicide. But the trial was a farce: there was no real evidence, the jury was biased, and not even the prosecutor claimed that any of the suspects had actually thrown the bomb. People all over the world were appalled. Today, it’s remembered as one of the darkest chapters in American labour history; it even served as the inspiration for International Workers Day, which we still celebrate on May Day every year.

Outraged, Goldman headed south to New York City to take up the cause. She arrived on a summer’s day in 1889, just twenty years old, with nothing but five dollars and a sewing machine. It didn’t take long for her to settle in, though. That very first afternoon, she headed straight for an anarchist café. That night, she went to see her first anarchist speech. Before long, she was giving her own speeches, earning a reputation as one of the most riveting lecturers in the country, passionately speaking about issues like labour rights, feminism, and political philosophy.

Today, many of her ideas seem pretty obvious — an eight-hour workday, legal birth control, gay rights — but in the late 1800s and early 1900s, even those ideas were deeply radical. She quickly attracted the attention not only of the press, but also the police. Once, she was arrested for giving a talk about methods of birth control. Another time, it was for inciting a riot. (“Ask for work,” she told a crowd of the starving and unemployed, “If they don’t give you work, ask for bread. If they do not give you work or bread, then take bread.”) She got so used to spending time in prison that she started to carry a book with her wherever she went, just in case she suddenly found herself in a jail cell without anything to read.

By the end of the 1800s, Goldman had become one of the biggest celebrities in the country. She was a front page staple. Red Emma, they called her. The Queen of Anarchism. The Most Dangerous Woman in the World.

And she could be dangerous. At least to some people. In those days, it felt like radical change could come at any moment. To many, the revolution didn’t just seem possible, it seemed inevitable. The young Goldman was willing to do whatever she could to help. If violence was necessary, that was okay with her. Even murder.

Just a few years after she arrived in New York, Goldman planned her own assassination. She and her lover, Alexander Berkman — who she met at that anarchist café on her very first afternoon in the city — plotted to kill Henry Ford Frick, the chairman of the Carnegie Steel Corporation. He was responsible for a bloody crack-down on a strike at a steel mill in Pennsylvania, hiring hundreds of Pinkerton detectives — private mercenary soldiers — to attack the striking workers, killing nine of them. In retaliation, Berkman burst into Frick’s office with a revolver, shot him twice and then stabbed him with a steel file. But the attack failed: Frick survived and Berkman spent the next fourteen years in prison.

Goldman, though, walked free. No one knew she’d been involved. And in time, her views on violence seemed to change. In later years, whenever asked, she would always distance herself from the use of force. “The only remedy for the people is anarchy… the form of revolution I want is bloodless… Anarchism does not believe in violence… Ideas are the greatest of bombs.”

But even then she wasn’t willing to condemn those who did resort to violence. When President McKinley was shot, the assassin claimed that he was inspired to do it by Goldman’s lectures. “Her words set me on fire,” he said. Goldman was arrested and questioned, but she refused to denounce the killer. “I have never been an advocate of violence,” she told the papers, but “I have always felt that when an individual resorts to violence it is the fault of the conditions above him that bring him to it.”

It was a theme she often repeated. For her, the real blame for any assassination always lay with systemic oppression. “As an anarchist, I am opposed to violence. But if people want to do away with assassins, they must first do away with the conditions which produce murderers.”

In the end, though, it wasn’t Goldman’s violence that got her kicked out of the United States. It was her pacifism.

When the First World War broke out, Goldman firmly opposed it. It was, she argued, a war to protect the interests of the rich: not a cause worth killing for. For the first three years of the war, her opinion was widely shared in the United States. President Woodrow Wilson even won re-election on a promise to stay out of the fight. But once the Americans did join the war, speaking out against it was no longer allowed. Opinions that had been widely shared suddenly became illegal.

Goldman, as always, refused to back down, giving speeches denouncing the draft. That gave the American authorities the opportunity they’d been waiting for: an excuse to get rid of her.

She was rounded up with a bunch of other anarchists and deported — all loaded onto a ship and sent to Russia. If they believed in revolution, the government told them, then the brand new Soviet state was the perfect place for them.

It wasn’t. At first, Goldman was actually pretty happy to be going back to Russia. As someone who had personally witnessed the horrors of life under the Tsars, she had high hopes for the Russian Revolution. But when she saw it with her own eyes, she realized it had gone terribly wrong. A meeting with Lenin confirmed her fears. They had replaced one totalitarian system with another. She fled the country. Goldman would spent the rest of her life angrily denouncing the Communists.

After that, she never really found another permanent home. She spent the rest of her life living out of her suitcase, forced out of one country after another. Finally, she arranged a marriage to a Welsh miner so that she could get a British passport. That gave her the right to live in Canada, where she would spend much of the rest of her life.

She would never again be allowed to live in her beloved United States, so she settled for the next best thing: she would stay in Toronto, just across the lake from Rochester, as close as she could get to her family and to the country she loved.

~~~

This was 1926. Toronto was still a deeply conservative city: a provincial town, deathly quiet on Sundays, staunchly British; not the kind of place you’d expect to find the world’s most notorious anarchist. And not the kind of place the world’s most notorious anarchist expected to find herself.

“I am so terribly cut off from intellectual contact,” Goldman once wrote while she was staying in Toronto. “I grow so depressed and unhappy at times it seems I could not stand it another day.” When the old anarchist criticized the lack of modern books in the library, the librarian gave her a blunt reply: “We do not buy books we consider immoral.” Toronto was, Goldman complained, “deadly dull.”

Still, it wasn’t all bad. The authorities in Toronto were more tolerant of her ideas than those in the United States had been — even if they did still screen all her mail. And there was a small, dedicated community of anarchists, artists and other progressive thinkers who were thrilled to have her in the city. They put her up in their homes, helped her to organize meetings and lectures, donated money to the causes she championed.

Plus, every time the Toronto Daily Star wrote about her — and they wrote about her a lot — it was in positively glowing terms. They called her “the world’s greatest feminine apostle of free speech.” “Brilliant.” “[A] speaker of notable excellence.” “You were impressed not only by her knowledge but also by her wisdom. She was a feminine Socrates conducting a brilliant dialogue on high and grave questions of human destiny and human conduct…”

“No woman of her generation,” the Star would remember after she died, “was more widely known or lived more fully than Emma Goldman. None clung more staunchly, through adversity, to her ideals…”

Goldman became a familiar name in the local papers and in lecture halls across the city. She spoke at the Labour Lyceum on Spadina, the Heliconian Club in Yorkville, the Hygea Hall on Elm Street, the Oddfellows Temple on College — always after a stiff drink of whisky to calm her nerves. Crowds of hundreds came to see her talk about feminism, free love, politics, literature… She thundered on about Sacco and Vanzetti, denounced Toronto schools for forcing all their boys to have military training, and railed against the dangers of Stalin with such passion that local Communists would attend her lectures just so they could shout her down. She warned of a coming war before Hitler had even taken power and gave speeches condemning him when many in Toronto still thought fascism was a perfectly acceptable idea.

She became a role model in a city starved for radical thought, inspiring those who were determined to make Toronto a more progressive place, and pressuring them to do better when she thought they were falling short. It was Emma Goldman who dared to speak about birth control back when it was still illegal, giving a lecture to a packed house at the Hygea Hall, earning a roar of applause when she declared contraception to be a right. (She was careful not to mention any specific methods — that would have been blatantly illegal and landed in her in the clutches of the Toronto Police Morality Squad — but she did hand out cards directing women to doctors who could help.) And it was Emma Goldman who launched the movement to ban Toronto teachers from using physical violence as a method of disciplining their students.

She would never fully settle in Toronto; she kept living out of her suitcase, like she always did. She had three long stays in the city, but would spend long periods away from it: writing her autobiography in France, visiting the anarchists fighting the fascists in the Spanish Civil War, going on speaking tours across Canada — she was even allowed to make one last trip to the United States.

But in the end, she always came back to Toronto. And that meant she was bound to run into Attilio Bortolotti eventually.

“I went to hear her,” he said, “and was flabbergasted by the way she spoke, with her energy, with the beauty of her sentences.” They were introduced after her speech, and eventually became close friends. Bortolotti volunteered as her unofficial chauffeur, happy to drive the old anarchist around the city as she gave lectures and attended meetings. Once, he even took her to Windsor, so she could gaze longingly across the river at the country she adored. (“She looked at Belle Isle and Detroit,” he said, “as though through the eyes of a lover. It was then that I understood how much America meant to her.”)

But this was 1939. All of Goldman’s dire warnings were about to come true: Hitler invaded Poland that September; the Second World War was underway.

That meant trouble for Toronto’s anarchists. With tensions rising, Bortolotti found his fascist enemies even more dangerous than before. “I was threatened with being ‘taken for a ride,'” he later remembered, “and for the only time in my life — I detest firearms and killing — I carried a pistol for a few months.”

Meanwhile, the authorities were cracking down too. As the paranoia of the war years set in, anyone with unusual ideas became a target for suspicion. Italians, even more than most; Mussolini didn’t enter the war immediately, but he had long been one of Hitler’s closest allies. It didn’t matter that Bortolotti was one of the city’s most ardent anti-fascists, or that he had been warning Canadians about the dangers of Hitler and Mussolini for years, or that Toronto’s own Nazi supporters were trying to silence him. In fact, many have suggested that the police were working with the fascists, who gave them tips about the anarchists they both despised.

“We organized demonstrations and street meetings at which I… spoke, and were attacked by mounted police,” Bortolotti remembered. “The authorities kept me under constant surveillance, and now they tried in earnest to deport me.”

It was the war that finally gave them their chance. When the country was at peace, the police had to respect civil rights. But when war was declared, the War Measures Act came into effect. Suddenly, the authorities had what one historian has called “quasi-totalitarian powers.” They were, according to another, “the most serious restrictions upon the civil liberties of Canadians since Confederation.” Habeas corpus was suspended. So was the right to a trial. Political groups could be banned by the government. So could entire religions. Eventually, they would use the War Measures Act to round up Canadians of Japanese descent and imprison them in internment camps — one of the most horrifying abuses of power in the history of our country.

By the end of the first month of the war, the government had expanded the Act to give themselves the power to censor any literature they didn’t like — and to arrest anyone found with this “dangerous” material. Hundreds of newspapers and magazines were shut down. Bookstores were raided, their owners arrested. Private homes were targeted too. Word began to spread among the Toronto anarchists: the police were raiding their homes one by one. Some rushed to burn their papers before it was too late.

They came for Bortolotti just a few days after the new rules came into effect. Before dawn one morning in early October, police on horseback surrounded his home on Gladstone Avenue (at the very top of the street, near Dupont). It was the Royal Canadian Mounted Police and Toronto’s notoriously brutal anti-Communist unit: the Red Squad. They burst into the house, grabbing all five anarchists who were staying there. “Get up,” they told Bortolotti, “and put on your Sunday best. You won’t be going to work for quite a while.” They searched the house, finding two guns with the triggers removed (the anarchists used them as props in plays) and seized all of Bortolotti’s books, magazines and newspapers: a library of 1,500 volumes. The police would burn them all.

Bortolotti was arrested. He would spend months in the Don Jail while the government worked to deport him. The original charges were dropped, and most of the other anarchists were released. But Bortolotti wasn’t a Canadian citizen and, having been threatened by Windsor’s chief of police, he hadn’t checked in at customs the last time he came across the border from Detroit. So the government was planning on sending him back to Italy anyway, where Mussolini’s fascist government would be waiting for him. If he was lucky, he would be thrown into a fascist prison. If not, he would simply be killed.

But not if Emma Goldman had anything to say about it. She was an old woman now, but she was still as defiant as ever. She leapt into action, asking her friends and allies to support Bortolotti’s defence. She organized meetings, raised money, hired a lawyer.

It wasn’t easy. For the first few months, it was hard to find anyone to support the cause. The newspapers refused to cover the case. And even liberal Canadians were reluctant to challenge the government during a time of war.

“Unfortunately,” Goldman complained, “there exists a conspiracy of silence among the daily journals… More sad is the complete absence of individual animation of civic sense, disposed to defend civil rights from the invasion of authority… no journal, no magazine socialist, liberal, unionist or other, in the US or Canada, said one word in defence of the arrested of Toronto.”

Meanwhile, Bortolotti was falling ill, suffering in the cold, damp conditions of the Don Jail. He came down with bronchitis, lost twelve pounds, ran a fever of 103ºF, and finally had to be transferred into the prison’s hospital ward.

Goldman refused to give up, but the campaign was taking a toll. It was, she admitted, “the hardest thing I have done in many years… [I am] frightfully weary of the struggle, and tired, tired beyond words.”

That’s when she suffered her first stroke.

~~~

She was playing a quiet game of bridge with friends, passing the time on a snowy evening before yet another meeting about Bortolotti’s case. “God damn it,” she complained at the beginning of a new hand, “why did you lead with that?”

Then, The Most Dangerous Woman in the World slumped over sideways in her chair. At first, her friends thought she’d dropped a card and was bending over to pick it up. But she’d actually suffered a massive stroke.

Bortolotti was out on bail when he got the phone call. “I don’t know how I drove without causing accidents,” he remembered, “because I was out of my mind. And I arrived on Vaughan Road there, and saw Emma, moaning—she couldn’t talk any more. Just to think that here was Emma, the greatest orator in America, unable to utter one word.” She was half-paralyzed. There was fear in her eyes. Embarrassed that her bare knee was showing, she pulled her skirt down with one hand. Moments later, the ambulance arrived.

She spent the next six weeks at Toronto General Hospital, where they did what they could for her. She was in tears for much of that time. When she was finally well enough to go home, her speech still hadn’t recovered; she struggled to say even a few words. Still, she kept working. She could understand conversations and read her letters, getting friends to write her replies.

Slowly but surely, her persistence had begun to pay off. People had started contributing to Bortolotti’s defence. First, it was an Italian-American anarchist newspaper. Then, a Yiddish-language paper in New York. There was a spaghetti dinner to raise money in Chicago. A play performed in Brooklyn. Another benefit in Massachusetts. Goldman had her letters to the editor published in The Nation, The New Republic and The Canadian Forum. Eventually, some leading progressive Canadians — like the leader of the federal CCF party (the forerunner of the NDP) — were convinced to join the fight. More letters were written. There were meetings with MPs. The Star published an editorial asking the government to halt the deportation. The tide was finally turning.

Goldman lived long enough to hear the good news: Bortolotti was free to stay. They’d won. He would eventually get his Canadian citizenship, start his own successful business, and play a leading role in Toronto’s anarchist community for decades to come. Thirty years later, the Globe and Mail would write about him fondly, calling him “the grand old man of Toronto anarchism.”

A few months after Goldman’s first stroke, she suffered a second. This time, she wouldn’t recover at all. She died in the middle of May at that same house on Vaughan Road.

A service was held at the Labour Lyceum, the same hall where Goldman’s resounding voice had once filled the air. For three hours people shared their stories and remembered her. The crowd was so big there wasn’t enough room inside the hall; the mourners spilled out onto Spadina. A full funeral in Chicago followed, where she was laid to rest next to the martyrs of the Haymarket affair who had inspired her to become an anarchist all those years ago.

She had gone down fighting, working hard for a cause she believed in right to the very end. It’s all she ever wanted.

Once, years earlier, the Star asked her if she had any regrets. “Whatever will happen will happen,” she said. “I hope to die on deck, true to my ideals with my eyes towards the east — the rising star.”

That’s exactly what she did.

A version of this post originally appeared on the The Toronto Dreams Project Historical Ephemera Blog. You can find more sources, images, links and related stories there.