The silence was broken by rapid staccato. Tap. Tap, tap, tap. Not gunfire but anxious fingers typing words onto creamy white paper with Canadian Legion War Services letterhead at the top. A soldier was writing a letter to a girl on the other side of the world.

Portrait of Harry Ward Macdonald with medals.
Harry Ward Macdonald enlisted ­into the Canadian Active Service Force on October 10, 1941.

It was the middle of March 1944, in the hills of central Italy. The Canadian soldier, a lieutenant commanding a tank troop in the 11th Canadian ­Armoured Regiment, was waiting for the rain to cease so his men could start ­moving again through the rough and sodden terrain. He didn’t write about what could lie ahead: the next assault on Monte Cassino, already one of the Allies’ deadliest battles in the Italian campaign.

The Canadian soldier, Harry Mac­donald, my grandfather, had sent Jacquelyn Robinson dozens of letters, spanning several years—letters written in spidery cursive by candlelight as rain ­pounded down on corrugated rooftops or amid the blasts of nearby shelling. His letters were often rushed or cut short, with some started and finished with hours or even days in between. He ­frequently apologized for his messy handwriting, hoping his words would be legible. One letter, sent five days before, written in haste, contained a question for which he anxiously awaited a reply. The letter had begun with a familiar two words, “Dear Jacquie,” and ended with a ­question: “Will you marry me?” But, impatient for an answer, he wrote her again.

It was March 14 when he found the typewriter. He needed his words to be as clear and as confident as his thoughts. “When I think that even now I could be calling upon you, taking you to a dance, going to a show and doing those things normal people could be doing I feel personally one of the greatest horrors of war—the separation of men from those they love,” he typed. “However, I suppose that if it wasn’t for the fact that I’m in the service it might have taken ­longer for me to realize just how lucky I am. I hope for the best, darling, no matter which way things turn out.”

He signed the bottom of the page, folded the sheet, and slipped it into an envelope and carefully wrote a Vancouver address. Now he waited, not knowing what would come first: death or a reply.

Love Letters

As a special feature for our online readers, Harley Rustad recorded his grandfather reading aloud some of the letters he wrote six decades before.

Original copy of handwritten letter
March 9, 1944: “Everything depends upon two big ‘if’s’. If you agree, and, if I come out of this show alive. No matter what happens, darling, I think you are a grand person and I’m very much in love with you. Whichever way you and fate dictate as the course I shall follow will be accepted as my just due. I have memories of you and of our willow tree that I cherish beyond all else. I love you, Jacquie, more than I can say. Will you marry me?”

Harry ward macdonald and Jacquelyn Ruth Robinson met at the 1941 May Day parade in Vancouver. He marched as an eighteen-year-old cadet of the Seaforth High­landers, and she accompanied the May Queen as a fifteen-year-old flower girl. Over the summer, Jacquie and Harry saw each other often. They picnicked along Kitsilano Beach and danced on the springy ­wooden floor of the Commodore Ballroom. The war in Europe seemed a world away from the breezy streets of ­Vancouver. But soon the gunfire and shelling, the gears and grinding, and the call to fight grew louder.

On October 10, 1941, Harry enlisted ­into the Canadian Active Service Force, one of more than 1.1 million Canadians and Newfoundlanders who would take part in the war. He filled in the attestation paper with the particulars of his young life to date: full name, address, religion, trade or calling, and next of kin. He said goodbye to his mother, his father, and his three younger sisters as he prepared to leave for training in Ontario. The evening before his departure, under the stars and drooping branches of a willow tree at the end of Jacquie’s family’s driveway, the young couple said good­bye. On a sign under the tree was an address—4545 Langara Avenue—that would come to represent not just home but hope.

Through the following winter and spring, Harry and thousands of other enlistees received basic weapons training at Camp Borden—the Canadian Forces base north of Toronto. Harry considered entering the air force, but when a sergeant he respected suggested he join the tank corps, Harry signed up. During training, he struggled with firing the 75mm guns of the thirty-tonne ­machines. “Someone could have stood beside the target and have been perfectly safe,” he wrote Jacquie. “Must have been that awful beer we have in the mess.” ­Instead, Harry found he was better at driving and commanding a tank.

Harry’s letters to Jacquie were few at the beginning, as if the two were testing whether the physical distance ­between them was going to prove too much. But the letters kept flowing back and forth—at first across the country and then across continents and oceans. During the Second World War, letters from loved ones and family were a crucial respite for soldiers on the front lines. They were a panacea and a lifeline and a boon to spirits. “It is almost impossible to over-stress the importance of this mail,” wrote then US postmaster general Frank C. Walker. “It is so essential to morale that army and ­navy officers of the highest rank list mail almost on a level with munitions and food.”

When he reached England in the spring of 1943, Harry was assigned to the Ontario Regiment and saw his first action against German troops in North Africa. Wherever he was deployed, he found paper and pen. “Letter writing has so many drawbacks,” he wrote Jacquie. “I want to be able to hold you and ask you in words that are spoken, not ­written. I want to see you in the flesh, not just to picture you in my mind.” Harry joked about being envious of those he called “Varsity wolves”—men who stayed home rather than enlisting, who could eat steaks and sip milkshakes rather than ­suffer through the bully beef and cold tea he was surviving on, or who could go out dancing rather than face the front lines.

Jacquie kept ­writing as she graduated from high school and began ­classes at the University of British Columbia. Mailed from Vancouver, her letters were sorted at a city post office, carried by train across the country, and then ­loaded onto a ship bound for England. There, they joined thousands of letters that had ­entered the Allies’ military mail system, then were dispatched to wherever Harry was listed as serving. From ports under ­Allied control, the letters were transported ­toward the front and then carried by hand to a base sorting facility—where, ­finally, they would reach Harry. Despite the distance, Jacquie’s letters often took only a few weeks to find his hand—but they were weeks of anxious waiting.

In the spring of 1944, the 11th Canadian Armoured Regiment continued to trudge through southern Italy toward Monte Cassino. After sending his proposal, Harry dispatched four subsequent letters explaining his intent and plans for their future ­together. “Remember our last evening under the guiding influence of the willow tree? What a hopeless case I was then. What an opportunity I missed,” he typed in the March 14 letter. “I think I did manage to blurt out, ‘I love you,’ in somewhat uncertain terms. Time has changed that uncertainty into the most definite thing I know.”

Then, on April 23, Harry was ­handed a blue, folded air-mail letter written and dated exactly one month before. In the top corner was a tawny Canadian stamp depicting the Parliament buildings in ­Ottawa, and on the back, in familiar handwriting, was the address under the willow tree. It was the reply from Jacquie he had been waiting for.

“Dear Harry,” she began, “There is a letter in front of me that just arrived today. The most wonderful letter in the world, I just can’t find words to tell you how wonderful it is. I have read it at least a dozen times in the last hour and I’m afraid I am still drying up the tears.”

She mentioned how she had collected pennies in the hope of saving enough to travel, to see England one day, and how they could go together. “I am ­only ­eighteen darling, but I do know what I want, and believe me, right now I must be just the happiest girl in the world. There is only one answer I could ever give you, and that is ‘yes!’”

Handwritten letters
Jacquelyn Ruth Robinson wrote hundreds of replies to Harry over the four years while he was away during the Second World War. On March 23, 1944, she sent him her answer to his proposal.

Over the following months, he would read this letter hundreds of times when he needed to fall asleep or when he needed a lift. His days were a tough slog—commanding, via headset, three Sherman tanks, each with a five-man crew, through wet terraced hills of the Liri Valley from skirmish to battle, from shelling to lull. “This war has just got to end soon or I shall go mad,” he would read, Jacquie’s voice coming off the page as clear as the day they met at the May Day parade. “But no ­matter how long it is I shall wait. I think I would wait ­forever for you just so long as I could always know you were somewhere ­waiting too.”

Two weeks after Harry received his reply, just before midnight on May 11, 1944, the fourth assault of the town of Monte Cassino began. Troops had been amassing quietly to try to maintain surprise for this final push. A coalition of nearly a dozen Allied countries took part, some offering artillery bombardment, some ground troops that formed a “pinch” around the town to force the German troops to flee. The Canadians sent in their tanks. The forces cleared the city and advanced on the ­Hitler line, a German defensive frontier that ran across part of central Italy. On May 24, the Canadian tanks breached the line. The Germans were in full retreat, but the success at Monte Cassino came at a cost: 55,000 Allied soldiers were killed.

Harry survived the battle of Monte Cassino. Many of his fellow soldiers and friends didn’t. His penchant for letter writing served him well in these tragic situations. One of his friends had asked Harry to write a letter to the man’s family if anything were to happen to him. When he died in a subsequent battle, Harry followed through, and the family replied with gratitude and a parcel of 1,500 cigarettes to be passed among his platoon.

Harry couldn’t hide the impact the loss of such compatriots had on him, often thinking about Jacquie and his own family. “To us, wounds and death are all part of the game—they’re taken for granted,” he wrote her. “But the long years of grief that always follow a war are borne by the people who are left behind.”

Through the rest of 1944, Harry and the tanks of the Ontario Regiment moved north through Italy, pushing back the German forces beyond the Trasimeno line. He relied on Jacquie’s words, which kept finding him even in the farthest reaches of the war. In their letters to each other, Harry and Jacquie wrote about finishing their degrees, about starting a family, and about travelling Europe in times of peace.

Wedding photo of Harry and Jacquie

In the first months of 1945, the war in Italy was grinding to a halt, but the fate of northwestern Europe was still uncertain. Harry’s regiment was among the Canadian soldiers who were withdrawn from Italy and boarded a ship in the coastal town of Livorno. One year to the day ­after Harry had proposed to Jacquie, he disembarked in Marseille, France, and began the month-long journey north to where the German army still lay ­entrenched in the Netherlands.

On the morning of April 13, Harry led a troop of tanks across the IJssell ­River in support of a battalion of British soldiers into the Dutch city of Arnhem. It was slow going, clearing machine gunners and snipers from buildings, but the tanks pressed hard to secure a route. As the ­attack in the city’s east faltered, the leading British platoon commander and a sergeant were killed. Chaos erupted. What happened next led to Harry being ­awarded the Military Cross, one of the highest medals of bravery for an officer of a Commonwealth country. His citation read: “At this critical juncture Lieutenant Macdonald at once assumed command and twice dismounted from his tank, under fire, to contact the leading section commander and to make plans for continuing to the objective. That this was achieved was due to Lieutenant Macdonald’s courageous example and to his complete disregard for his own safety. His conduct was a great inspiration to the men of the platoon and was the main factor in the success of the operation.”

Almost to the end of the war, Harry’s tone with Jacquie was unwaveringly positive and upbeat—a shield, perhaps, for her as well as for himself, from reality. But when Harry crossed the border into Germany, his faith in a bright future that he had ­written so often about began to flicker.

For a soldier who thought he had seen the worst, nothing could have prepared him for when he entered Germany. “The horse and cart, with all the family possessions stowed in it, going back home, is becoming a common sight in Germany,” he wrote on April 12, 1945. “Refugees—what complete pathos that word implies! Never a smiling face, never a quick step, never a glimmer of hope. Only the little children in their ignorance seem unaware of the grim present and the even ­grimmer future. The man who starts the next war will be one who will not have seen Germany as it is today....After seeing those people I realize that our ­problems, Jacquie, are infinitesimally small.”

Then, on May 7, having been appointed intelligence officer for the Eleventh Canadian Armoured Regiment, responsible for documenting the movements and goings-­on of his men, Harry sat down at a typewriter and wrote the report for the final days of the war. “This evening the BBC told the world that Prime Minister Churchill would announce to-­morrow would be VE Day,” he typed. “To the soldier in the line the news didn’t mean much. The Regiment accepted the end with very little enthusiasm. There will be little, if any, celebration. There seems to be a feeling of satisfaction at having finished off a good job, but ­nothing more.” The next day, after noting the ­weather, troop movements, and how a captured pilot from Victoria, BC, who had crashed in the Netherlands three months prior had been rescued from the SS, Harry finished his regimental intelligence summary ­quietly: “The war is over. The announcement came to-day.”

Harry knew where to direct his gratitude. “By all the rules I shouldn’t have pulled through—but I did,” he wrote Jacquie the month the war ended. “You were responsible for that. I’m convinced of it. All line soldiers have someone watching over them, or so we believe. In my case it was you.”

In June, Harry was given leave to England, where King George VI pinned a purple-­and-white ribbon with a silver medal, his Military Cross, to his jacket at a ceremony in Buckingham Palace. Come autumn, Harry finally allowed himself to go from stealing a glance west over his shoulder to turning to face it. On October 7, 1945, Harry wrote Jacquie one final letter from Europe. “The moment I see you I know I’ll forget everything about these last years. I’ve almost forgotten them now....There are a great deal of paths to choose, my only problem is which one to start walking down. There’s only one thing I’m certain of. No matter which way we go, we’ll go together....All my love, Harry.

I was twenty-eight, recently home from a year abroad, when my mother handed me a worn navy-blue garment box, torn at the edges. “I think you should read these now,” she said to me. Inside were dozens of postcard-sized envelopes, tied with yellowed string in small bundles.

My grandparents never really spoke about the anxiety, turmoil, and uncertainty of those early years. They were among the postwar twentysomethings who prioritized careers and families ­rather than the activism that would define the next generation. By the time I was handed the box, the story of how they forged their relationship had faded from memory. I learned that, less than a year after arriving home in Vancouver, on ­August 19, 1946, Harry and Jacquie were married. Then, in 1948, at twenty-five, Harry won the Rhodes Scholarship to study economics at Oxford University, and the couple finally saw England together. Before leaving, while in the hospital with his and Jacquie’s newborn baby, Harry spoke to the Vancouver Daily Province—the newspaper ­wanted to interview the local veteran who had recently been awarded a scholarship. He is quoted as saying he wanted “a family of five girls more than an Oxford Ph.D.” After their first, the couple had four more girls.

Reading their letters and digging into their history led to other stories, apocryphal ones told to me in conversations with family. How at the end of the Italian campaign, before being redeployed to the northwestern front, my grandfather chose to drive his tank into Lake Trasimeno and sink it rather than let it fall into potential enemy hands. Or how Harry wasn’t the only soldier during the war my grandmother wrote letters to. There were, I was told, two others, including an airman who, after she had decided on my grandfather, died in a plane crash over the English Channel. The airman’s parents blamed my grandmother, saying that their son had died of a broken heart.

I’ll never know where the truth in these stories lies. War has a tendency to blur the lines between fact and fiction. And one wonders how many more tales of other relationships forged during this time are out there—all being pushed deeper into the catacombs of lore and memory. Every year, as the men and women who endured both front lines of the war enter their nineties, fewer remain. Both my grandparents are gone now: my grandmother died on November 17, 2011, after they had celebrated their sixty-fifth wedding anniversary that summer; my grandfather died on January 2, 2014. Seventy years to the month before, he had written to Jacquie. “I’ve got something now, that no matter what happens, will always be with me. No tough knock, whether it be physical, mental or spiritual, will ever change me now, because I have a faith in the future and a faith in you that will outlast anything.”

Original photos, letters, documents
The author combed through hundreds of love letters, war documents, photographs, and archival material relating to his grandparents’ story.

In that blue cardboard box, in the correspondence between a young man and a young woman who were sep­arated by conflict, I found neither myth nor fable but honest words of both pain and love. Between 1941 and 1945, Harry and Jacquie sent hundreds of letters across the world to each other. They spoke of mundane details and of big plans for their future. He sent her more than 200 dispatches and replies, around one for every week he was away, containing tens of thousands of words. She kept every letter.

For Harry, it wasn’t possible to lug around the hundreds of letters he received from her. While on the move over sand, terraced hills, and cold mud, some letters were lost, some were ruined, and some were left behind when the matter at hand outweighed personal possessions. But, wherever he went, safeguarded among his few belongings, Harry kept only one. He boarded the ship in Portsmouth, England, bound for Halifax on October 11, 1945, with a single blue ­letter, its edges now brown and worn, that folded into itself—the ­letter that held the one word that ­mattered most: yes.

This article originally appeared in the November 2018 issue.

Harley Rustad
Harley Rustad (@hmrustad) is a senior editor at The Walrus and the author of Lost in the Valley of Death: A Story of Obsession and Danger in the Himalayas (2022) and Big Lonely Doug: The Story of One of Canada’s Last Great Trees (2018).
Vicky Lam
Vicky Lam is a Toronto-based photographer whose work has been published in Reader’s Digest, Toronto Life, and Best Health.