Ernest Hemingway's Toronto Ties

September 20, 2023 | Pamela

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Ernest Hemingway (1899–1961) was an American novelist who won a Pulitzer Prize for Fiction and Nobel Prize in Literature. He's known for titles such as The Sun Also Rises, A Farewell to Arms and The Old Man and the Sea.

What you may not know is that Hemingway had a four-year association with Toronto and its newspapers. Many credit Hemingway's time in Toronto as being pivotal for his transition from newspaper to novel writing.

This post looks at Hemingway's ties to Toronto and includes historical photos and rare materials from our Special Collections.

Collage of photo of a young Ernest Hemingway and old Toronto postcard with newsprint in background
Postcard of Toronto (approximately 1921) and passport photo of Hemingway (1923).

Hemingway arrives in Toronto

In the summer of 1919, Hemingway caught the attention of Harriet Connable while vacationing at Walloon Lake in Michigan. Harriett and her husband Ralph lived in Toronto. Ralph oversaw the Canadian operations of department store chain F. W. Woolworth Company.

The Connable family were looking for a caretaker and tutor for their 19-year-old son who had a disability. Harriet was impressed by Hemingway’s stories about his service as an ambulance driver in Italy during World War I (although the born-storyteller embellished his experiences). Hemingway's relationship with his own family in Chicago had become strained, so he accepted the job.

On January 8, 1920, Hemingway arrived in Toronto for the first time. He moved in with the Connables at 153 Lyndhurst Avenue in the Casa Loma area of Toronto. He was 20 years old.

Vintage view of large manor with stately entrance gates
Hemingway stayed at 153 Lyndhurst Avenue when he first arrived in Toronto. Here's the home in 1982. View on Digital Archive.

The 1920s was a decade of great change for Toronto. The city was becoming more prominent, but many residents worked long hours for low wages. It was heavily industrialized. Automobile ownership increased, congesting the downtown streets.

When Hemingway arrived, the Toronto Transit Commission had not yet been established. The current Union Station and the Royal York Hotel had not been built. Prohibition was in effect. The population of the city passed half a million, with 62% born in Canada and nearly 30% born in the United Kingdom. 

Postcard of black and white city from above with old Toronto City Hall in middle and few large buildings surrounding it
Postcard of Toronto's old City Hall, 1919. View on Digital Archive.

Hemingway's interest in newspapers

Hemingway always had ambitions to become a fiction writer. His family encouraged him to attend university, but he believed the best way to learn the craft was by writing for newspapers. Many of his literary heroes — Stephen Crane, Mark Twain, Ring Lardner, George Ade and Jack London — began their careers as newspaper reporters.

He had a brief apprenticeship as a cub reporter for the Kansas City Star in Missouri in 1917. This experience taught him how to mine the facts of a story and describe them simply and directly using the paper’s style sheet.

Hemingway was anxious to continue his practical education. He asked Ralph Connable for an introduction to the Toronto Daily Star (renamed Toronto Star in 1971). It was one of five newspapers in Toronto at the time. The others were The Globe, The Mail and Empire, Toronto World and the Toronto Telegram, which was the Star's main competitor.

Side by side images of old multi storey building and a vintage cover of newspaper The Toronto Star Weekly
Left: The Toronto Daily Star, the largest newspaper offices in Canada, at 18-20 King Street West in 1913 (view on Digital Archive). Hemingway worked on the second floor. 
Right: Cover of Toronto Star Weekly from the 1920s, held in our Special Collections at Toronto Reference Library.

Starting at Toronto Star Weekly

Hemingway was given a chance to be a freelance reporter with Toronto Star Weekly, a weekend publication affiliated with the Toronto Daily Star newspaper.

The publication tried to compete with Sunday World, a highly successful magazine that offered inspiring fiction, humorous sketches, comics, children’s tales and advice for the lovelorn. To draw readership, the Star Weekly began to pay for popular fiction and entertaining human interest stories. This was a perfect time for Hemingway to come on board.

Hemingway’s first story was about Mayor Tommy Church, a long-serving politician, but it was rejected for publication due to its heavy-handed tone.

Hemingway scholars believe his first story in a Toronto paper was published on February 14, 1920. It was a short, unsigned Star Weekly piece titled “Circulating Pictures a New High-Art Idea in Toronto.” It was on March 6 that Hemingway had a story for the first time under his byline — “Taking a Chance for a Free Shave” — about getting a free shave at a barber college.

Unlike his eight months at the Kansas City Star (where he never received a byline), Toronto Star Weekly editors mostly left it up to their reporters to suggest ideas. Hemingway's distinctive style was encouraged, and his writing flourished. His features were closer to fiction than hard news. He often wrote about sports, a theme that would appear in his novels.

Opened book of bound newspapers with many columns of text including one with a byline by Ernest Hemingway
Hemingway's first byline appears at the top, just to the right of the centre crease in the Toronto Star Weekly on March 6, 1920 (click image to enlarge). This original newspaper is preserved in our Baldwin Collection of Canadiana.  We encourage researchers to use our Toronto Star Historical Newspaper Archive to help reduce wear and tear on the original newspapers.

Moving abroad

In May of 1920, Hemingway’s job in Toronto as a companion to Junior Connable ended. He went to Michigan and later Chicago, where he met his first wife Hadley Richardson.

He continued to write stories for The Star. In February 1921, one of his former editors offered him a job as Toronto Daily Star’s foreign correspondent in Europe. Six months later, out of financial necessity, Hemingway accepted the job and moved to Paris with his new wife. He was known on the Paris literary scene, becoming part of a group of American writers and poets known as The Lost Generation.

Hemingway's travels through the continent and the company he kept inspired the next phase of his writing. Hemingway wrote about bullfights, drinking and conflict as well as other topics that he later included in his fiction.

Close up of vintage Toronto Star paper with article titled Bull Fighting is Not a Sport by Ernest Hemingway
Hemingway's article "Bull Fighting Is Not a Sport — It is a Tragedy" in an original October 20, 1923 issue of Toronto Star Weekly. Part of our Baldwin Collection of Canadiana. Read it online.

Return to Toronto in 1923

Hemingway and his wife Hadley stayed in Paris until the late summer of 1923 when they moved back to Toronto. They were expecting their first child and wanted him to be born in Toronto. The city’s hospitals had an excellent reputation for caring for newborns and their mothers. Hemingway had been offered a position on The Star’s daily edition, which meant steady work. The Hemingways stayed briefly at The Selby Hotel at 592 Sherbourne Street.

Hemingway found working for the Toronto Daily Star’s city editor Harry C. Hindmarsh difficult. Hemingway was constantly sent out of town on what he felt were menial assignments. On the first week on the job, Hindmarsh sent him to Sudbury, Ontario to write a story about an alleged swindle involving a British coal company. Leslie McFarlane, the first author of the Hardy Boys stories, was a reporter at the Sudbury Star at the time. He told Hemingway that there was no coal in Sudbury — so there was no story. McFarlane later wrote that Hemingway, trying to salvage something from the trip, wrote a piece about Sudbury that accidentally implied it was full of sex workers.

Sepia postcard of building in city with trees and caption reading Selby Hotel 592 Sherbourne Street Toronto Canada
Postcard of Selby Hotel in Toronto, approximately 1920, where the Hemingways briefly resided in 1923. Today, the building still thrives as a hotel and restaurant. Hemingway’s name can be found on the menu. View on Digital Archive.

The Arts and Letters Club

Hemingway was set to become a member of the Toronto’s Arts and Letters Club, an organization founded in 1908. Many key figures in creative and performing arts in English-speaking Canada belonged to the private club during the first half of the 20th century, including members of The Group of Seven.

On September 10, 1923, Hemingway was nominated for membership by William Main Johnson, Toronto Daily Star's promotions manager. Hemingway’s membership was seconded by painter Thomas Garland Greene. Unfortunately, Hemingway didn't pay his initiation dues, so he never officially became a member of the private club. (A photo of Hemingway paired with this anecdote hangs in the basement of the club.)

Black and white photo of old building on street
St. George's Hall at 14 Elm Street, built in 1891, is home to The Arts and Letters Club. Photo from 1979. View on Digital Archive.

Hemingway's first child is born in Toronto

On October 10, 1923, Hemingway returned to Toronto after covering a news story in New York. An employee of The Star met him at Union Station to let him know that his wife Hadley had given birth at Western Hospital. The Hemingways named their son John Hadley Nicanor. (John Hadley was one of Hemingway’s favourite pen names, and Nicanor paid homage to a matador Hemingway admired.) They nicknamed the baby Mr. Bumby, later shortened to Bumby.

Side by side images of a postcard of a hospital with lots of trees in front of building and a birth certificate for Hemingway's son
Left: Postcard of Western Hospital in Toronto, 1910. Right: Birth certificate of John "Bumby" Hemingway, December 10, 1923  from Ancestry Library Edition.  View larger version of certificate.

Final Toronto residence

The Hemingways had been looking for a suitable home before the birth of their son. After staying three weeks in the Selby Hotel, they found a small apartment in a then-new Cedarville Mansions. Located at 1599 Bathurst Street, it was not far from the Connable residence, Hemingway’s first home in Toronto.

Hemingway signed a year-long lease for Unit 19, paying $85 a month. However, the lease was broken when Hemingway quit the newspaper on January 1, 1924 following an altercation with editor Hindmarsh. When he left, Hemingway had filed almost 200 stories for the newspaper, and he had published his first two volumes of fiction: Three Stories and Ten Poems and In Our Time. The literary world was beginning to pay attention.

Hemingway’s last article — "Must Wear Hats Like Other Folks If You Live in Toronto" — appeared in Toronto Star Weekly on January 19, 1924 under the pen name John Hadley. The publication coincided with the Hemingways return voyage to Paris.  

During his association with the Toronto paper, Hemingway was provided with money, mobility and access to people and places that he later turned into fiction. Many credit his time with the newspaper as pivotal for his transition to novel writing.

Black and white view of low rise brick apartment building
1599 Bathurst Street, 1980. Hemingway lived here and there's now a heritage plaque dedicated to him at the residence. View on Digital Archive.

Explore further with additional TPL resources 


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