Two baby boys were born at the end of the 19th century. One, in 1895, to a working-class Irish family named Ryan in Toronto, the other, in 1899, to a well-off, upper middle-class family named Hemingway in the conservative Chicago suburb of Oak Park, Illinois. Both Norman “Red” Ryan and Ernest Hemingway were determined to escape the lives into which they were born. Ryan sought a higher standard of living than the hard scrabble existence he saw his parents lead. Hemingway wanted to escape the conservative community of Oak Park. A community he later described as a neighbourhood of wide lawns and narrow minds. He wanted to be a writer, a different kind of writer, not a doctor like his father. As Hemingway was growing up, Teddy Roosevelt was either president of the United States or a prominent figure on the national and international scene. Roosevelt’s mantra was “Get action. Do things; be sane; don’t fritter away your time; create, act, take a place wherever you are and be somebody; get action.” We know from Hemingway’s life story that it was a philosophy he embraced and attempted to duplicate. As they grew up, both boys upset their families with their attempts to “Get action.” Ryan chose crime as his perceived road to the high life. Hemingway moved to Paris and worked hard to live an artist’s life and have his talents recognized by avant garde literati such as James Joyce, Ezra Pound and Gertrude Stein. After some successes, both were thwarted in their early ambitions. Ryan by the long arm of the law. Hemingway by life, his wife, Hadley’s, unexpected pregnancy. Time, Hemingway concluded, to do the responsible, conservative Oak Park thing and leave his enjoyable and rewarding ex-pat life and do something he should do but he dreaded. On September 10, 1923, when Ryan, age 28, was a literal prisoner in Kingston Penitentiary for bank robbery and Hemingway, aged 24, was imprisoned by an existential crisis, their paths would cross.On September 10th, Hemingway was wrestling with the fact he had placed restraints around himself by leaving Paris and starting a job as a staff reporter at The Toronto Daily Star. Restraints that would clearly make it impossible for him to do the thing he wanted to do the most – write. On September 10th, Ryan went over the penitentiary wall with four other inmates and headed for the woods north of Kingston. Red Ryan took action to release himself from the prison he found himself in. And Hemingway, who knew before he even left France he’d made a big mistake, had a front row seat. September 10th was his first day on the job and his boss Harry Comfort Hindmarsh sent him to cover Red Ryan’s escape.Even when no longer officially assigned to the story, as a Star employee, Hemingway could follow all of Red’s exploits as they came in over the wires. And what Hemingway saw in Red Ryan was the man he wanted to be at that moment and was not. Courage. Red had exhibited plenty. Nerve. Risked his life for freedom. Need money? Rob a bank in broad daylight. Teddy Roosevelt said, “Be Somebody” and Red Ryan certainly was. At that moment, he was famous, infamous, notorious. Much better known than a wanna-be writer putting in eighteen hour days at a job he didn’t like. “Take action!” Teddy Roosevelt said. Red Ryan had taken plenty. And criminal activity notwithstanding, Hemingway was a little jealous.Hemingway was so taken with Red Ryan’s story, his escape and then capture, that in 1926 after the success of The Sun Also Rises, when Hemingway was now a somebody, a big deal somebody in the literary world, he recorded in his notebook that his next novel could be about Red Ryan. Carlos Baker, Hemingway’s premier biographer, quoted from the notebook in his book Hemingway A Life Story (p. 166): “It will not be the story of a weak disappointed youth caught and sucked up by fate. It will be the story of a tough kid lucky for a long time and finally smashed by fate.”Smashed by fate. Are we talking about Red Ryan or the fledgling Ernest Hemingway here? Because that is how Hemingway was feeling in Toronto in 1923. That is why he was fascinated by Red Ryan’s brave attempts to remedy his situation. That is why Hemingway quit his job after three months, went back to Paris and made literary his history. Smashed by fate. Nope. Just like Red, he got action.