York was born in Toronto and studied political science and history at York University. He began his journalistic career as a young reporter and summer staffer for The Globe and Mail, covering both sports and news during his high school and university days.
York first wrote for The Globe as a teenager in 1974, after a reporter who visited his class recruited him to write about amateur sports. Not long afterwards, popular Globe sports columnist Dick Beddoes took York under his wing and became his mentor.
After his graduation, then-Globe managing editor Clark Davey hired York full-time for sports coverage and asked him to inject objective and tough reporting into his work.

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