Frank Pickersgill had a plan. It was December 1941. He’d been locked up by the Nazis for months, shipped from one internment camp to another. Starving and sick, he’d been forced to exist on nothing more than hot water, mouldy potato soup, and bread. He’d seen horrors, witnessed fellow prisoners murdered, and lost forty pounds off an already thin frame. But now, there was hope. Frank Pickersgill was going to escape.
His days as a student at the University of Toronto must have seemed like a distant dream. He’d been in Europe for a while now, having continued his studies in France, doing his postgraduate work at the Sorbonne, living the life of a young, struggling writer in the cafés of Paris when the war broke out. He hadn’t left right away, had tried to stick it out during the first few quiet months of the war. He’d written the first English translation of Jean-Paul Sartre’s new novel Nausea, and helped pay his bills by working as a milkman.
By the time he decided to leave, it was too late. The Germans were approaching. The Canadian authorities had already evacuated; they couldn’t help. So, as the black smoke of Nazi war machines reached the City of Love, Pickersgill climbed onto his bicycle and raced off into the French countryside, joining the endless lines of refugees heading south out of Paris as German tanks rumbled into the city from the north. He pedalled endlessly through the French countryside, looking for a way out. The last ships to England had already left. Frightened villagers were suspicious of strangers: some nearly killed him, thinking he must be a German spy. In the end, as Hitler’s forces took control of France, Pickersgill was rounded up like most of the Canadians and other British subjects who were still stuck in the country. Now, he was back in Paris, at the St. Denis Internment Camp.
But if he had his way, he wouldn’t be there for long.
The first step: he got assigned to cleaning duty. That meant he worked one day a week in the administrative buildings. They were outside the barbed wire. There was nothing between him and freedom but a big brick wall.
Next: he needed to get access to the censor’s office. It had a barred window that looked out onto the street. Luckily, one of the German officers was a bit careless with his key. When he forgot it in the lock, all it took was a few moments. Pickersgill’s co-conspirator kept a lump of clay in his pocket. They pressed the key into it, making a perfect mould of its shape, and then put the key back where they found it. When Pickersgill got a visit from a friend, he secretly passed the mould on to him, and when the friend returned, he had a brand-new key ready to pass back to Pickersgill. A perfect copy.
Then: they had to wait for the office to be empty. They’d done their research: the censor spent every weekend with his mistress. They simply waited until the end of the day on Saturday and slipped right into his office with their copy of his key. He wouldn’t be back until Monday.
Finally: they had to deal with the bars on the window. They had a plan for them, too. Pickersgill’s accomplice got so much mail from friends and family that the guards at the post office had stopped searching his packages. They didn’t notice when a friend mailed him a loaf of bread with a hacksaw and three blades baked inside. It took four hours of loud sawing, every moment excruciating as they expected to be discovered, but in the wee hours of the morning, the bars finally fell free.
They waited until morning, when the streets were full of people, then slipped out the window, put the bars carefully back in place, and melted away into the crowd. It would be weeks before the Germans finally figured out how they’d escaped.
The very next day, Frank Pickersgill was on his way out of Paris. For the next six months, through the summer of 1942, Pickersgill would live in the French countryside. There, he found plenty of people willing to help: to welcome him, conceal his true identify, and give him shelter — including a couple of Ernest Hemingway’s old Parisian friends, the famous writer Gertrude Stein and her partner Alice B. Toklas. He was even able to find work with the French Resistance, translating anti-Nazi propaganda.
But Pickersgill was determined to do more. He’d fallen in love with France during his time in Paris. The thought of his beloved city suffering under Nazi occupation was too much to bear. Even before he’d been captured, he’d been driven to pitch in. “I am so full of shame and disgust that I must do something,” he wrote in French, “if I don’t, I could never come back.”
He was still weakened and thin as a result of his months in captivity, but he was desperate to do something substantial — to a make a real, concrete contribution. “I was in the war up to the neck,” he wrote, “and I think I should have died of spiritual starvation had I been wrenched away from it. In others words I suppose in a sense I had become a fanatic.” Refusing to return home all the way to Canada and safety, he worked instead to get himself onto a flight bound for England. There, he was sure, he would find the opportunity he was looking for: a chance to join the fight.
And he was right. The day after he got off the plane in England, he was approached by officials from the British government. He was a scholar from a prominent diplomatic family who had survived Nazi internment camps, escaped captivity, and worked with the French Resistance. He was exactly the kind of person the Allied secret services were looking for. Frank Pickersgill was going to be a spy.
So was Ken Macalister. He was doing it for love. He’d once been one of the most promising young law students at the University of Toronto. So promising, in fact, he became a Rhodes Scholar, given a scholarship to study at Oxford University in England. But Macalister’s interest in the origins of Canadian law wasn’t just limited to its British roots. He wanted to know about its French origins, too. So he convinced the Rhodes Trustees to let him study at the Sorbonne for a while. And it was there in France that he met Jeannine.
A bit of luck brought them together. Looking to improve his French, Macalister arranged to spend the summer of 1939 living with a professor and his family in Normandy, so he could be fully immersed in the language. Jeannine was the professor’s daughter. And as they spent those long summer days together near the coast of France, the two quickly fell in love. They were married before autumn arrived, ready to spend their lives together.
But then, just weeks later, the war began — and German tanks wouldn’t be far behind. Macalister had promised the Rhodes Trustees he would immediately return to the safety of England when war broke out, but now he fought for every moment with Jeannine. He lied repeatedly, made up excuses, and dragged his feet, all so he could stay in France as long as possible. He even tried to enlist in the French army, but was rejected because of his poor eyesight. Even still, he was determined to do his part to keep France — and his new wife — safe from the Nazis. So, in the end, he made a heart-wrenching decision: he would return to England as he’d promised, leaving Jeannine behind, and try to join the British army.
Those days in London were an incredibly difficult time for the young law student. He was rejected from the military again. And his separation from Jeannine soon became even more rending; she was pregnant, expecting their first child that spring, and he wouldn’t be able to see her. They could barely communicate at all, able to exchange only a few letters sent through the Red Cross or smuggled out of France. In spring, terrible news arrived: Jeannine’s labour had gone poorly. She was okay, but the baby hadn’t survived. And with Germany launching its invasion of France just weeks later, there was no safe way for Macalister to join his wife and console her. She would soon be trapped behind enemy lines.
The Canadian was more determined than ever. He would to do everything in his power to join the effort to liberate France — and Jeannine with it.
That’s when he was presented with an unusual opportunity.
They called it “The Firm.” Its official name was the Secret Operations Executive (SOE). It was created in the summer of 1940, in the terrifying months after Hitler’s forces had swept across Europe and the Nazis began to bomb Britain in anticipation of an invasion. The Firm would be responsible for strengthening anti-Nazi resistance in the occupied countries of Europe through sabotage and death. Winston Churchill called the ministry overseeing it “The Ministry of Ungentlemanly Warfare.” Its mission, as he put it, “was to set Europe ablaze.”
Thousands of secret agents would be parachuted into Nazi-occupied territory over the course of the war, where they assumed false identities and recruited sympathetic locals. They carried out sabotage against the Germans, planned assassinations, and prepared secret armies of resistance fighters ready for the day when the Allies returned to liberate their countries.
In Prague, they assassinated a leader of the SS. In Scandinavia, they sabotaged atomic research facilities. In Italy, they would capture the entire city of Genoa. One German commander would later estimate that The Firm shortened the war by six months.
But it was incredibly dangerous and difficult work. Many of the spy networks were uncovered. Many agents were captured, tortured, and executed.
Canadians played an important role in the secret service right from the very start. One of the organizations that evolved into the SOE was founded by a newspaper magnate from Montreal: Sir Campbell Stuart. And one of Britain’s most successful spymasters was an industrialist from Winnipeg: William Stephenson — said to have inspired the character of James Bond. With his help, a secret spy school was built on the shores of Lake Ontario. Camp X stood just outside Toronto, on the border between Whitby and Oshawa. Hundreds of recruits were trained there — including the children’s author Roald Dahl and maybe even James Bond’s creator, Ian Fleming. Graduates of Camp X would become spies for the SOE, the FBI, and the forerunners of the CIA. Today, the place where it once stood is a public park called Intrepid Park, in honour of William Stephenson’s code name.
And Canadians weren’t just working behind the scenes. Some were signing up to become spies themselves. When Ken Macalister was approached to join the SOE, he leapt at the opportunity. In the secret service, his poor eyesight wouldn’t be as much of a liability as it was in the regular army. In fact, his thick glasses would help his disguise. It was settled: he would become a secret agent, join the fight against the Nazis, liberate France, and free his wife.
Little did he know the terrible truth: he would never see Jeannine again.
Frank Pickersgill was about to fall in love, too.
Training for The Firm was a thoroughly rigorous process, designed to weed out all the candidates who weren’t up for such a demanding assignment. They learned how to fire guns and explode grenades; they ran obstacle courses and climbed ropes; and they learned sabotage, Morse code, and how to sneak up on a sentry and kill him quietly, even while drunk. They practised their French, studied maps, and carried out elaborate practice missions.
The Firm had some worries about Pickersgill. The Germans knew what he looked like thanks to the long months he’d spent in their prisons. And even if they’d forgotten, the story of his escape had been published in his hometown Winnipeg newspaper along with a photo — the Nazis might have seen it. He also had a terrible habit of talking in his sleep — in English. Not ideal for a man going undercover as a French citizen.
But he was also clearly driven, with a sense of purpose and a deep dedication to the cause. He wrote about his training with unbridled enthusiasm. “I’m enjoying it as I’ve never enjoyed anything in my life before.… I’ve been in a permanent state of exhilaration [since my escape] on the crest of a wave which kept getting higher and higher as each frontier was crossed, and which now, instead of subsiding, seems to be going on up. I don’t know where it’s going to land me, but it’s damned good while it lasts.”
He would be partnered with Ken Macalister, the two graduates of the University of Toronto taking on the Nazis together. Their training complete, there was nothing left to do but wait for the phone to ring with the details of their mission. And it was while they were waiting that Frank Pickersgill would fall in love with Alison Grant.
She was from an influential Toronto family: her relatives included famous academics and philosophers; her uncle was the governor general, Vincent Massey. Her background was a lot to live up to, and she took the responsibility that came with her heritage seriously; she was determined to make a real difference. Having moved to England to attend art school, she found herself in London as the war began, living with a couple of other young women in a perfectly ordinary-looking apartment above a dairy. But apartment 54A wasn’t an ordinary apartment at all. It was a safe house.
Grant now worked for MI5. Her flatmates worked for The Firm. The two new Canadian spies would stay there until they got their phone call.
When he arrived at 54A, Pickersgill was nursing a broken heart. His escape from occupied France had taken him through Lisbon, where he’d coincidentally met another woman named Grant. Jacqueline Grant had also escaped from France after spending time in a Nazi internment camp. And during those brief but exciting days together in Portugal, the two fell in love. By the time he left for England, Pickersgill was confident they would soon be married — he simply wanted to make sure he could afford it before he officially proposed.
It wasn’t until Jacqueline joined him in England that they realized their relationship wasn’t quite as profound as they’d hoped — the thrill of their escape made their feelings seem stronger than they actually were. “We didn’t have much in common to talk about,” she would later admit. After a long and difficult conversation, hours of painful discussion, they decided to break it off.
That was good news for Alison Grant. When she first met Pickersgill, she described him as “terribly thin and hollow-eyed,” still recovering from his ordeal, “but with such a sparkle in his eye.” When he was back to full health, he was incredibly strong and tall, with the off-beat charm of an academic and rumpled clothes. He was excited about politics, philosophy, and ideas. And it was far from just talk; he was about to parachute into France to fight the Nazis.
He was smitten, too. “Alison is a frightfully good thing and terribly amusing,” he wrote in a letter back home just after meeting her. “She is certainly one of the most amusing people I’ve ever met,” he added later, “and we have a riotous time making New Yorkerish surrealist jokes at one another.” Within a couple of months, they were truly and deeply in love.
The five of them — the three Canadians and the women who’d taken them in — became inseparable during the six months they were together, waiting for the phone to ring. They spent their nights dancing, going to the movies, or sitting at home around the fireplace deep in conversation. Grant helped them pick out clothes for their French disguises — rubbing them in dirt and ripping up the lining to make sure they looked authentically worn.
But all the while, the threat of death hung over them. They knew the men would soon be called away on their dangerous mission. Once, when Grant and Pickersgill went to a movie that featured a double agent, things got a bit too real for her. But he was resolute. “Frank knew exactly what he was doing and getting into.… [The movie] got pretty grim, and I began to feel uncomfortable, and suggested we leave. Frank said quite coldly: ‘If I can stand it surely you can.’ That was that.” All they needed to do was survive the war. Then, they were sure, they would spend the rest of their lives together.
The telephone finally rang. It was time for the spies to begin their mission. Grant saw Pickersgill off, saying goodbye to him on a street corner, watching him walk away in his disguise. It was the last time she would ever see him.
On a moonlit night in June 1943, the two Canadian spies floated down out of the sky above France. Their plane had taken off in England, flying low over the English Channel to avoid detection, heading toward a field outside the French town of Blois. Signal lanterns marked the spot where the Canadians were meant to land. In those early morning hours, they leapt from the plane into the empty sky, their parachutes bursting open and bringing them gently toward the ground. It must have been an exhilarating moment. “Absolute peace and silence” is how Pickersgill described the experience during his training jumps. “It’s the nearest thing to a perfect dream that could be imagined.”
For a moment, all seemed to be going exactly to plan. Macalister would twist his ankle a bit on landing, but it was nothing serious. And the two French spies who would serve as their initial contacts were there waiting.
Pierre Culioli started the war with a motorcycle unit, but was wounded and captured — only to be released on compassionate grounds when his wife was killed by Italian bombers, giving him the chance to rejoin the fight as a secret agent. His partner was Yvonne Rudelatt, a forty-seven-year-old divorcee and grandmother, who’d been recruited while working at a club in London frequented by members of the secret service. Together, they pretended to be a married couple who’d been bombed out of their home and forced to become refugees. She had a knack for sabotage. He was skilled at organizing drops, just like the one that was now bringing the Canadians floating out of the sky.
Culioli and Rudelatt were meant to help the Canadians get started. The Firm had already established a large spy network in the region. Upon their arrival, Pickersgill and Macalister would set up a new subcircuit, codenamed “Archdeacon.” Pickersgill would be the organizer, tasked with making new contacts, sussing out the people he met, and then bringing those he absolutely trusted into his confidence — and into his spy network. Macalister would be his radio operator, their vital link to the outside world and their only way of communicating with their bosses in London.
Even if everything went exactly to plan, it would be an incredibly dangerous mission. And it soon became clear that things wouldn’t go to plan at all. In fact, things had begun to go horribly wrong before they’d even hit the ground.
Just days before the two new secret agents were scheduled to arrive in France, the British parachuted in a shipment of explosives to be used in sabotage. The drop was a disaster: the explosives detonated when they hit the ground. The Germans heard it. They would soon send more than two thousand troops into the region to investigate and search for spies. An agent on the ground sent The Firm an urgent message: they should abort the upcoming drop; it was too dangerous for the Canadians to parachute in.
But the message was either ignored or was never even received in the first place. The Canadians were sent anyway, dropping into an area that was about to become thick with German soldiers on the alert for anyone who seemed suspicious.
After months of preparation, the mission would last less than a week.
The spies laid low for a few days, until they decided it was safe enough to catch a train to Paris. But on their way to the station, they were pulled over at a checkpoint. While the soldiers bought the story Culioli and Rudelatt told them, the two Canadians weren’t so lucky. They were taken inside the town hall for questioning.
It was a tense moment. Culioli and Rudelatt waited in the car, motor running, hoping their colleagues would somehow be able to convince the Germans they were just ordinary Frenchmen — despite their iffy command of French. There’s no way to know what happened inside that town hall, but when the Germans came out and called for Culioli and Rudelatt to follow them, they assumed the Canadians had been found out. Culioli floored it, peeling out of town and away across the country roads, trying to outrun the three German cars that followed.
They didn’t make it far. A roadblock loomed up ahead, and as Culioli sped forward to ram it, the guards opened fire. One bullet sliced through Culioli’s hat. Another wounded Rudelatt in the head. He swerved, aiming for a brick house, trying to kill them both and destroy the car in a ball of flame that would burn all the evidence and equipment in the trunk. Instead, the car glanced off the house and landed in a field. All four spies were taken into custody.
The Canadians would spend months being interrogated, tortured, and beaten in prisons, Gestapo headquarters, and concentration camps across France and Germany. But they refused to give up any secrets. When the Germans tried to bribe Pickersgill with a lavish meal in Paris, he responded by grabbing a bottle of wine off the table, smashing it into a jagged weapon, slitting the throat of his guard, escaping into the hallway, killing another soldier who tried to stop him, and then jumping out the second-floor window into the street below, breaking his elbow in the process. As he hobbled away down the road, he was brought down by a shower of German bullets. He survived but was thrown back into prison.
Still, even without the Canadians’ help, the Germans had a lot to go on. They used the information they found in the trunk of the car to launch their own covert operation. They had agents assume the identities of the Canadians, pretending to set up the spy ring as planned, and then arresting anyone they were able to lure into it. They even met with one of the greatest of all British spies. Noor Inayat Khan met with the two German operatives who were pretending to be Pickersgill and Macalister, barely avoiding capture. It was the beginning of the end for her; now the Germans knew what she looked like. She was betrayed and arrested soon after.
And that wasn’t all the Germans found in the trunk of the car. They also had Macalister’s radio. They sent messages to England, pretending the dispatches were coming from the Canadians. They were convincing enough that the British kept parachuting in money, weapons, supplies, and spies — which were all seized by the Germans as soon as they hit the ground. It wasn’t until The Firm asked the women of apartment 54A if they’d like to send their Canadian friends a message for the holidays that they began to get suspicious. They sent a playful greeting: “The tea samovar is still bubbling at 54A.” When the answer came, it was painfully dry and generic: “Thank you for your personal message.” The women knew it couldn’t possibly have come from the light-hearted Canadians. They must have been captured.
The realization must have come as a crushing blow to the women those secret agents had left behind. Germans weren’t in the habit of showing mercy to Allied spies. They can’t have known it for sure, and must have held out hope, however faint. But with that impersonal message, the truth began to reveal itself. They would never see Frank Pickersgill and Ken Macalister ever again. Jeannine Macalister would never remarry. Alison Grant would fall in love again. She would marry a diplomat called George Ignatieff, who would one day become the chancellor of the University of Toronto. Their son Michael would eventually grow up to become the leader of the federal Liberal Party.
Pickersgill and Macalister would spend more than a year in Nazi prisons. But as the end of the war drew near, they continued to insist they would never give their captors any help. That meant they weren’t needed anymore. In the summer of 1944, as the Allies pushed the Germans back across the continent, the Canadians were taken to Buchenwald. They would spend their few remaining weeks surrounded by the horrors of one of the Nazis’ most notorious concentration camps.
The end came on a September afternoon. They and fourteen other men were marched to the crematorium, their guards shoving them down the steps into the basement: a long, concrete room lined with big hooks known as “the corpse cellar.” The executioner was waiting for them. He ordered their hands bound and a noose of thick wire wrapped around each of their necks. It was there in that basement that Frank Pickersgill and Ken Macalister were hanged, dangling from the hooks until they died. Then their bodies were fed into the ovens.
A big stone tower was built at the University of Toronto after the First World War. The Soldiers’ Tower stands next to Hart House, a memorial to the students and staff who’d fought and died. And with the end of the Second World War, a new wall was added to the arch that passes through it. More room was needed for the names of the dead, hundreds of them chiselled into the stone. The names of Frank Pickersgill and Ken Macalister can still be found among them. And next to the tower, a small garden was planted: a flowering tribute to two Canadian spies who gave their lives trying to free Europe from the Nazis and return to the women they loved.