How Hemingway Broke His Lease
Plus: bootleggers and smugglers, walking tours, and more...
This week, I thought I’d share a chapter from The Toronto Book of Love…
A train pulled into Union Station. It had been travelling overnight from New York City, bringing the British prime minister to Toronto as part of his North American tour. His stop in the Big Apple had been big news. Reporters flocked to cover the event, including a young journalist from the Toronto Star by the name of Ernest Hemingway. Soon, he’d be one of the most celebrated authors in the world, but at the time he was making do with a modest salary from the newspaper. He was coming back to town on the very same train as the visiting prime minister, spending much of the sixteen-hour journey leisurely drinking and joking around with the other reporters. But as the train came to a stop at Union Station, he rushed down the steps onto the platform. He’d just received word, a few kilometres back: his wife, Hadley, had given birth to their first child. He needed to get to the hospital as quick as he could.
Toronto had built a new train station in the decades since George Brown’s triumphant return to the city. The second Union Station was an opulent building with three grand towers; the biggest train station in Canada when it first opened. It stood on the south side of Front Street, overlooking the lake, next to the spot where the modern Union Station stands today. Toronto Western Hospital, where Hadley was recovering with their new baby, was a couple of kilometres away. Hemingway was in a hurry.
But as he raced through the station, he was stopped by a fellow reporter, a colleague from the newspaper who’d been sent by his editor to collect him. He was under strict orders to head straight to the Toronto Star headquarters, a distinguished four-storey building on King Street. Hemingway had missed a scoop while he was in New York and his boss was furious. According to another paper, the deputy mayor of New York had insulted Britain; big news in British Toronto. But Hemingway didn’t care. He had bigger things to worry about right now. He stuffed his notes into the hands of the reporter and rushed away.
He’d met his wife at a party in Chicago a few years earlier. He was the most handsome man there — at least as far as Hadley Richardson was concerned. He was nearly a decade younger than she was — just twenty while she was twenty-eight, already at risk of becoming an aging spinster by the standards of the time. For years, she’d been living a half-life, nursing her dying mother. But now that her mom had passed way, Richardson was ready for love. And she found it there in that handsome young writer wearing an Italian cape.
He proposed within weeks. The engagement was far from uncomplicated: Richardson wasn’t the only woman in love with Hemingway; his other admirers included the mutual friend who’d introduced them. But their bond was strong. He wrote her so many love letters he worried he would be ruined as a letter writer forever, “Like a pitcher with a dead arm.” And she wrote more than a thousand pages back. “You’re absolutely a flame of love,” she told him, “and sweetness and understanding and strength and my I love you beyond anything. Why you’re All.” They were married on a September day in Michigan in 1921.
Two years later, in Toronto, when the contractions started, Hadley didn’t realize what was happening. Not right away. She was distracted, hanging out at their friends’ house, when the labour pains began. It was almost midnight by the time she understood, and nearly too late as he rushed down Bathurst Street to the hospital. “We got there in the nick of time,” she remembered. “Of course, I missed Ernest terribly. He should have been there with me, suffering.” But it went quickly after that. Just a couple of hours later, she gave birth to a healthy baby boy.
Hemingway was elated when he finally arrived to meet his new son. It’s why they’d come to Canada in the first place, taking a break from their beloved Paris because they heard Toronto had the best doctors. And in that moment, it must have all felt so worth it as they gazed down at their new baby boy: John Hadley Nicanor Hemingway — or Mr. Bumby, as they would call him. At the sight of his first child, Hemingway broke down in delight, exhausted and relieved to be reunited with his wife. That joy wouldn’t last forever. Soon, they’d be back in Paris, and Hemingway would fall in love with another woman; their marriage would end in heartbreak and betrayal. But for now, in that moment, they were truly happy.
The next day, Hemingway reported to his editor’s office at the Star. His boss tore into him for missing the scoop and for heading directly to the hospital to see his wife and child instead of straight to work. Hemingway was enraged. He was already frustrated by his heavy workload, which too often kept him from writing his fiction, and by the fact that his editor had shipped him off to New York when Hadley was nine months pregnant and due to give birth any day. His complaints would eventually drive him into a legendary act of defiance. There are many different versions of the story, but some remember Hemingway as being so incensed that he angrily typed out a venomous, sixteen-page screed against his boss. He then taped it together and pinned it to the office notice board for all to read. It was so long the pages curled up on the floor.
Hemingway was out of patience. He’d always hated Toronto. He first moved to the city in 1920. He’d been invited by a wealthy Canadian who saw him give a talk to a women’s group in Michigan. He showed up in his military cape and medals and told harrowing tales of his adventures during the First World War — complete with the war wound he’d earned as an ambulance driver on the Italian front. Many of those tales were completely imaginary, he’d only served for two months and the cape was new, but Harriet Connable didn’t know that. Hemingway was a good storyteller. She was so impressed she offered him a job: hanging out with her son, who was introverted and had a disability, in their mansion near Casa Loma. She hoped the adventurous Hemingway would rub off on her teenager. That job in Toronto led to Hemingway’s gig with the Star, and the paper eventually sent him to Paris as a foreign correspondent, writing dispatches back to Canada from the cobblestoned streets of France with his new wife, Hadley, by his side.
It wasn’t until she got pregnant that they came back to Toronto, living in a tiny apartment on Bathurst, a few blocks north of St. Clair, in a building now known as “The Hemingway.” It wasn’t much. While they did manage to squeeze in a grand piano for Hadley to play, there wasn’t even enough room left over for a full-sized bed; instead, they had to pull a Murphy bed down from the wall every night.
But Hemingway’s dislike for Toronto was the product of more than his cramped living conditions. This was 1923. Toronto was still deeply conservative, staunchly British, and thoroughly reserved. Boring, according to many. It was a city where hotels weren’t allowed to rent rooms to unmarried couples. Where on a Sunday, it was illegal to shop, to swear, or to ride a toboggan. Drinking was illegal on any day of the week: Prohibition was still years away from being repealed in Ontario. Toronto wasn’t exactly the ideal home for one of history’s most infamous alcoholics.
While he praised the TTC — “No city in the world has a better-run and more comfortable streetcar system than Toronto” — and wrote lovingly about the old trees in Queen’s Park, Hemingway was miserable in the city. In his letters to the poet Ezra Pound, Hemingway called Canada a “fistulated asshole” and claimed, “The people are all merde.” To Sylvia Beach, owner of the Shakespeare & Company bookstore, he wrote, “Canadians are all tapettes [pansies] at heart under all the big free open spaces.… It is a dreadful country.” Thanks to the blow-up with his boss, he was done with the Star. That meant he was done with Toronto, too. He was determined to leave the city as soon as possible.
On Boxing Day 1923 — the day after he secured his Christmas bonus — Hemingway quit the paper. But there was still one hitch: the lease on their tiny Bathurst Street apartment. If they simply tried to move out of the building, they’d be caught by the landlord, who would certainly call the police. So, Ernest and Hadley hatched a plan. Every time a friend stopped by to say goodbye, they asked them to take a single piece of furniture out with them when they left. Ever so slowly, one belonging at a time, they secretively moved out of the apartment. When the place had finally been emptied out, they made their move. They slipped away, undetected, and headed south to Union Station.
Not three months after he arrived on that train from New York, Hemingway was waiting for a train to take him back. From there, they would catch a steamship to France. They were leaving Toronto forever, heading home to their beloved Paris, back to the artists and the cafés, back to their famous friends. In Europe, without his work for the Star to distract him, Hemingway would finally have time to finish his first novel. The Sun Also Rises was published just two years later, dedicated to Hadley and their Toronto-born son. But by the time the book went to press, their marriage was coming to an end. Fame was waiting for Ernest Hemingway in Paris, but so were the days of betrayal, heartbreak, and divorce that would haunt him to the end of his life.
The Toronto Book of Love is available from all the usual places, including your favourite local bookstore or directly from my publisher here.
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Toronto’s Most Notorious: Bootleggers & Smugglers
Over the last few months, I’ve been giving a whole new series of lectures for the Toronto Public Library — four talks about some of the most notorious criminals and crimes from our city’s history. And the last one is coming up this Friday!
Toronto's Most Notorious explores the shadowy underbelly of Toronto's past with true crime and mystery stories about the scoundrels, rogues, killers and crooks whose crimes have shocked and fascinated our city for generations. I’ll be sharing wicked tales of vice and villainy and how they've shaped the history of the place we call home.
Here are all the details about the final lecture:
TORONTO’S MOST NOTORIOUS: BOOTLEGGERS & SMUGGLERS
Friday, July 11 — Noon — Online
Toronto's history is filled with tales of criminals creeping through our city's shadows. In this talk, we'll head into the secret speakeasies, backrooms and brothels of days gone by to uncover those stories. Storyteller and historian Adam Bunch will introduce us to everyone from the smugglers who snuck shipments up the Scarborough Bluffs to the jazz age rumrunners who defied Prohibition to the gangsters who got rich off the rewards of bootlegging.
Six Summer Walks With The LIFE Institute!
This summer, I’m hoping to lead more walking tours than ever before! In addition to my usual public tours (more on that below) and the private bookings for which I’m always available (more info here), I’m also heading out to explore the history of the city with the LIFE Institute!
Walking Through Toronto’s History is a series of tours exploring the city’s past. We’ll take six strolls through six neighbourhoods across the city’s core. It’s all being offered through the LIFE Institute, which provides educational programming for “older adults” (50+) and is affiliated with Toronto Metropolitan University’s G. Raymond Chang School of Continuing Education.
Description: Summer in the city! And here’s your chance to get out and explore Toronto’s history on a fascinating series of walking tours led by an expert guide. We'll spend six weekly walks diving into the city's past in the places where that history happened, learning about the neighbourhoods that have transformed Toronto. We’ll begin at the Waterfront with the city's early history — from ancient footprints to the War of 1812 — and follow that up by visiting Old Toronto to learn about the riots and rebellion that broke out over the future of Canadian democracy. Next, we'll explore the city's industrial past and its growth into a booming Victorian metropolis through the story of the distillery's evolution. Our fourth walk will take us through The Ward and Kensington Market, two neighbourhoods that laid the foundations for the multicultural Toronto of today. And then we'll head to Yorkville to learn about that area's days as a hippie haven home to one of the world's greatest music scenes. We'll finish by exploring the strange histories hidden among our towering modern skyscrapers, exploring the financial district as we uncover tales about everything from curses and omens to grisly deaths and mysterious disappearances.
When: Wednesdays at 3pm from July 9 to August 13.
Where: Various neighbourhoods around the city’s core!
(If you mention you learned about Walking Through Toronto’s History from me, I believe you might also be able to get a discounted rate on a membership with LIFE.)
From the Ward to Kensington Market: A New Walking Tour!
I’ve got a new public walking tour coming up! The Ward and Kensington Market are two neighbourhoods that helped transform Toronto, laying the foundations for our multicultural metropolis back in the days when our city was still a stubbornly British place. So, we’ll spend a Saturday afternoon walking between those two old neighbourhoods, exploring some of those stories about the city’s multicultural roots along with other tales hidden in the streets between them — everything from anarchists to runaway horses to demon ghosts.
When: Saturday, July 26 at 3pm.
Where: Meet in Nathan Phillips Square (near the Toronto sign). We’ll end in Kensington Market.
Length: Approximately 1.5 to 2 hours.
Price: Pay what you like!
QUICK LINKS
The best of everything new in Toronto’s past…
DOOMED PLANETARIUM NEWS — It seems as if the McLaughlin Planetarium is entering its final days. The beloved attraction has sat abandoned next to the ROM for decades, having been closed thanks to provincial cuts back in 1995. And now the University of Toronto has announced it will be moving forward with its plans to demolish the building — as well as a portion, it seems, of the 124-year-old Falconer Hall next door — to be replaced with a new home for the School of Cities along with spaces for other departments and a recital hall. Read more.
NAMING NEWS — The Toronto Star’s Deborah Dundas writes about the renaming of Dundas Station and why she’s okay with it despite her pride in her family name. “Cities are organic, changing and growing as the needs and size of their population demand. Sometimes when new information comes to light … change occurs.” Read more.
CEREMONIAL MACE NEWS — On Bluesky, Jeremy Hopkin shares the story of the day the United States returned the ceremonial mace they took from our town during the War of 1812. They brought it back on the fourth of July in 1934. Read more.
OLDEST QUEER SPACE IN CANADA NEWS — Chris Middleton interviews Friends of Hanlan’s about the deep LGBTQ+ history of Hanlan’s Point Beach for blogTO. Read more.
NOT GOOD NEWS FOR FOXES NEWS — Keena Alwahaidi takes a look back at the days when “mass hunting events were held on Toronto streets.” Read more.
CROOKED KNIGHT NEWS — Want to live in the same Rosedale mansion as Sir Henry Pellatt of Casa Loma fame? The home he lived in after leaving his famous folly (having been brought down by his own corruption, a scandal which also took down a bank and cost thousands of ordinary Canadians their life savings) is up for sale. Misha Gajewski took a peek inside for blogTO. Read more.
PODCAST NEWS — The Muddy York podcast has been hard at work, with a slew of recent episodes released about everything from the CN Tower to the Don Valley to the Beaches and more. Listen to them.
TORONTO HISTORY EVENTS
GROUP OF SEVEN DAY: POSTCARD FROM THE WOODS
July 7 — 10:30am to 4pm — Art Gallery of Ontario
“The Group of Seven imagined in paint a Canada of ancient lakes and woods, Arctic vistas, and the magic of the northern lights. We’re bringing Algonquin Park and Algoma to Walker Court for Ontario's first-ever Group of Seven Day. With more than 200 works by the Group of Seven on view, immerse yourself in their art and ambition and try your hand at still life painting in Walker Court. We’ll give you the art-making materials, the inspiration, and a postcard to write home about it—we’ll even provide the canoe!”
Free with general admission!
NEWSGIRLS: GUTSY PIONEERS IN CANADA’S NEWSROOMS
July 8 — 6pm — Runnymede Library
“Join Donna Jean Mackinnon, Toronto author, freelance writer and former Toronto Star reporter, as she documents the lives of 10 leading female reporters who started their careers during newspaper's Golden Age. Presentation includes a slew of vintage photos and intimate anecdotes.”
Free!
WAR & TERROR IN THE TOWN: WALKING TOUR
July 11 at 10:30am — Town of York Historical Society
“In this walking tour, join us as we explore the beginnings of the area that would become the Town of York, the events leading up to the War of 1812, the Battle of York, its aftermath, and everyday living conditions while we walk the original 10 blocks of the early city.”
$17.31
UPRISING & UPSETS: WALKING TOUR
July 11 at 7pm — Town of York Historical Society
“In this walking tour, join us as we explore some of the major riots, uprisings, and upsets that occurred in the Town of York and the early City of Toronto throughout the 18th and 19th centuries, and the outcomes that led to lasting societal and political changes.”
$17.31
1920s GARDEN PARTY AT SPADINA MUSEUM
July 20 — 12-5pm — Spadina Museum
“Be transported to another era as you experience the sights and sounds of summer at Spadina in the 1920s. The historic gardens and sprawling lawns will be set for picnics and lawn games. Visitors take part in art-making workshops and tour the public rooms of the historic mansion. Live music, dancing, and a costume parade fill out the day’s activities. Shop for unique products, prepared food, and drinks from diverse local vendors. You may also pack your own picnic. Spadina’s annual event is inspired by a garden party organized by Mary Austin in support of the Women’s Art Association of Canada in 1928. This year's event celebrates the theme of Home. Wear your best historical 1920’s dress from all cultural and ethnic backgrounds.”
$28 for adults and seniors; $20 for youth and children.
MUSIC WALKING TOUR OF YONGE STREET
July 22 at 3pm; August 6 at 4pm; September 2 at 4pm — Downtown Yonge BIA & Mackenzie House Museum
“From choral songs to jazz ensembles, and blues club crawls to Massey Hall, join us for a walking tour along Yonge St. that considers the vibrant musical history of downtown Toronto. This tour will examine the venues, recordings, instruments, and performances that enriched the Yonge Street music scene through the lens of the virtuoso Canadian jazz pianist, Oscar Peterson, whose centenary is celebrated in 2025! We will start the walk at the St. James Cathedral grounds in Old Town Toronto and make our way to Turko Parkette in the Downtown Yonge neighbourhood. Tour is led by the staff of Mackenzie House Museum.”
Free!
WHEELING THROUGH TORONTO: A HISTORY OF THE BICYCLE AND ITS RIDERS
July 24 — 6:30pm — Deer Park Library
“Cities around the world, including Toronto, are embracing the bicycle as a response to the climate crisis. This is not the first time the bicycle has come to our rescue, proving itself a loyal friend during times of crisis, including the world wars and the COVID pandemic. In Wheeling through Toronto, author Albert Koehl takes the audience on a 130-year ride through the rich history of the bicycle in Toronto. By understanding how we got here, we can begin mapping a way forward, one in which the potential of cycling is maximized.”
Free!
THE LOYALISTS ARRIVE IN YORK: WALKING TOUR
July 25 — 10:30am — Town of York Historical Society
“In this walking tour, explore the early history of the Town of York, with a focus on the Loyalist experience during the American Revolution, the War of 1812, the Battle of York, amidst the backdrop of the Old Town neighbourhood.”
$17.31
I WAS NEVER HERE: CONVERSATIONS WITH A CANADIAN SPY
July 25 — 6pm — Agincourt Library
“Have you ever wondered if you have what it takes to be a Spy? What does being an intelligence officer actually look like? Have all your questions answered by Andrew Kirsch, former Canadian Security Intelligence Service officer as he discusses his new book, I Was Never Here, revealing behind-the-scenes the work of a Canadian spy.”
Free!
VIOLENCE & SCANDAL IN MUDDY YORK: WALKING TOUR
July 25 at 7pm — Town of York Historical Society
“In this walking tour, explore the scandalous side of Little Muddy York as we walk through the surviving built environment of the original 10 blocks of Toronto and learn about the intriguing stories that would have been the gossip of the day. Invasions, epidemics, and hangings, oh my!”
$17.31
THE PAPER TRAIL TO THE 1923 CHINESE EXCLUSION ACT
July 31 — 6:30pm — Toronto Reference Library
“Join award-winning community historian Catherine Clement as she shares the findings of her landmark project, which excavated true personal stories during the years of the Chinese Exclusion Act, a tragic yet mostly forgotten chapter of Canadian history. Her book The Paper Trail to the 1923 Chinese Exclusion Act is the first to explore the broad range of 'human experiences' of exclusion. The pages reveal haunting tales of tragedy, loss, and despair as well as powerful examples of courage, perseverance, and resilience. They chronicle the lives of ordinary people caught in extraordinary times. Crowdsourced from the fragments of memories of hundreds of Chinese Canadian families across Canada, as well as extensive research, many stories and images are being shared publicly for the very first time.”
Free!
HOME GAME: TORONTO LOVES BASKETBALL
Until October 12 — Wednesdays to Sundays — Harbourfront Centre — Museum of Toronto
“Home Game: Toronto Loves Basketball chronicles the love story between a city and a sport. Even before the Toronto Raptors and the rallying cry “We the North”, basketball in Toronto was deeply rooted in the evolving social and cultural conditions of our city and its people. From the Canadian invention of basketball to the early women’s game in 1895, to the first professional game played by the Toronto Huskies in 1946, and the recent creation of the Toronto Tempo WNBA team, these milestones chart the development of the sport in our city. This exhibition, along with a series of profiles on fellow Torontonians, explores how the relationship between basketball and Toronto is unlike any other in the world.”
Free! (Donation suggested.)
HERITAGE TORONTO WALKING TOURS
Until Autumn — Various dates and times — Heritage Toronto
“Through our events, including tours, community discussions, the Heritage Toronto Awards, and more, Heritage Toronto engages the public to reflect on the city’s heritage.”
Usually $9.85.
AT HOME IN TORONTO
Until November 13 — Wed to Sun, 11am–5pm — The Market Gallery
“What does home mean to you? Discover rarely seen artifacts from the City’s collections and items from community members, the exhibition invites you to explore the many ways we define, create, and carry home with us. From a World War One soldier’s return ticket home to a precious family object stewarded by multiple generations, you’ll encounter belongings, voices, and stories of Toronto artists, makers, entrepreneurs, and community leaders as they share their unique perspectives on belonging, identity, and place. These powerful objects offer fresh, heartfelt perspectives on what it means to find, make, or remember home.”
Free!
THE 52: STORIES OF WOMEN WHO TRANSFORMED TORONTO
Until December 20 — Wednesday to Saturday, 12pm to 6pm — Museum of Toronto
“Did you know that 52% of Torontonians are women? Join Museum of Toronto as we bring their stories to life. The 52 is a project that celebrates the impact that women have had on our city, the world, and beyond. Building on a multi-year research project, our newest exhibition will celebrate the lives of 52 women who have shaped Toronto as we know it. Spanning from the 1800s until today, this exhibition shines a spotlight on the change-makers, rebels, and revolutionaries within Toronto’s 52%. While some of these women’s stories are well known, others have gone relatively untold until today. See how many names you are familiar to you — step into their shoes, learn their stories and discover the ways they have transformed Toronto.”
Free! Donation suggested.