Michael Winter was born in 1965 in Jarrow, England. His father was an industrial arts teacher, who moved the family to Newfoundland three years later, eventually settling in Corner Brook. After high school, Winter went to Memorial University, graduating in 1986 with a BA in economic geography.
Winter’s first short story collection, Creaking in Their Skins, was published in 1994. In 1999, editor John Metcalf at The Porcupine’s Quill published his second book of stories, One Last Good Look. Winter moved to Toronto in 1999, where he published his first two novels: This All Happened (2000) and The Big Why (2004).
Much of Winter’s fiction chronicles the life and adventures of his fictional alter ego, Gabriel English. This All Happened, for example, is organized as a fictional diary, with 365 entries describing Gabriel’s life in St. John’s, his relationship with filmmaker Lydia Murphy, and the progress of the novel he is trying to write. The book was nominated for the 2000 Rogers Writers' Trust Fiction Prize and won the inaugural Winterset Award.
The Big Why was a historical novel narrated by real-life American artist Rockwell Kent describing the time he spent in Brigus, Newfoundland, in 1914. Kent was eventually deported from Canada on suspicion of being a Nazi spy.
Winter was one of the judges of the 2006 Giller Prize, and his line drawings illustrate Noah Richler's This is My Country, What's Yours? A Literary Atlas of Canada (2006). He serialized short teasers for each chapter of his third novel, The Architects are Here (2007), on Facebook.
The Death of Donna Whalen (2010), his fourth novel, is described by the author as “documentary fiction”. It uses court documents, transcripts and other material to tell the story of Donna Whalen, a St. John’s woman stabbed to death, possibly by her boyfriend Sheldon Troke. The book is based on the 1993 murder of Brenda Young.
Winter’s novels and short stories have been described has having in common “a free-flowing, vibrant dialogue, presented without quotation marks. His characters' speech ranges from contemplative and meandering to rapid fire and piercing.”
Lynn Coady, reviewing The Death of Donna Whalen, wrote that Winter’s use of documentary material “shows amazing faith in the power of story itself, the sheer ability of raw human character to transfix us. In stepping back from centre stage and turning the spotlight entirely on this devastating array of intersecting lives and deaths, Winter has enacted some of the most powerful storytelling of his career.”