It was, as you might expect, Hemingway’s proclivity for storytelling that landed him a job in Toronto. While cottaging with his family in Petoskey, Michigan, Hemingway was asked to deliver a speech at the local women’s club, sharing with the audience his experiences as a soldier with the Italian army during the First World War, from which he had recently returned.
Of course, Hemingway had never fought with the Italian forces. He had been a volunteer ambulance driver with the Red Cross. He was handing out chocolates and cigarettes to Italian soldiers when his leg was seriously wounded by mortar fire. After extensive surgery and a long period of convalescence, he was sent home to the United States, having served for two months. This, however, did not make for a good story. So Hemingway procured a custom-tailored Italian officer’s uniform and cape, and made up a better one instead.
Harriet Connable, a wealthy Torontonian who was vacationing in Petoskey with her husband, Ralph, was so moved by Hemingway’s speech at the women’s club that she asked if he would consider staying at the couple’s mansion in Toronto. Harriet believed that the courage and pluck Hemingway showed in recovering from his leg injury might serve as an inspiration to her invalid son, Ralph Jr., and so she offered him a position as the boy’s caretaker and mentor while she and Ralph Sr. travelled to Florida on holiday. Through the elder Ralph’s business connections, Hemingway was able to secure a job writing features for the Star Weekly.
Hemingway was excited by the prospect of working for the Star, but less enthusiastic about taking care of Ralph Jr., whom he regarded as an irredeemable bore. The Connables insisted that Hemingway, who was adept at nearly every sport he tried, should attempt to interest their sickly son in athletics. One such attempt entailed taking Ralph to watch the Toronto St. Patricks, who, seven years later, would be renamed the Maple Leafs. Although the St. Pats were not a particularly skilled team in 1920, they were an undoubtedly truculent one, and Hemingway admired their scrappy style of play. That’s right: Ernest Hemingway was a Leafs fan.
Apparently, though, Hemingway's liking for Toronto diminished sharply over time.