In the autumn of 1864, at the age of fifteen, William Osler was sent to boarding school in Barrie, Ontario. The school was run by a friend of his father, and all five of his brothers had been there before him. "Willie" and two of his classmates soon became known as "Barrie's Bad Boys" due to their propensity for pranks and misbehaviour. Osler was a good student nonetheless, and excelled at sports.

Due to the waning reputation of the Barrie Grammar School, in January of 1866 Osler's father enrolled him at Trinity College School, which had been founded the previous year in Weston, Ontario, by the Reverend W. A. Johnson. Trinity College School was meant to prepare its students for Trinity College in Toronto, and was based on an English style of discipline and governance; Osler thrived under this system and was soon made a prefect. It was during his time in Weston that Osler first announced his intention to follow in his father's footsteps and become a minister in the Anglican Church.

With this profession in mind Osler entered the Arts program at Trinity College, Toronto, in the autumn of 1867. But by this time Osler had already formulated an intense interest in biology, or what was then known as natural history - a popular pastime among educated men at the time. This interest had been sparked by Reverend Johnson at Weston, and was further encouraged by his teacher Dr. James Bovell at Trinity College. Osler gradually spent more and more time with scientific pursuits, and soon abandoned the idea of a career in the church. Osler enrolled in the Toronto Medical School in 1868. He quickly became dissatisfied with the quality of education offered there, and left Toronto for Montreal's McGill Medical School in 1870.

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