James "Jimmy" Simpson (1873 – September 24, 1938) was a Canadian trade unionist, printer, journalist and left wing politician in Toronto, Ontario. He was a long time member of Toronto's city council and served as Mayor of Toronto in 1935, the first member of the Cooperative Commonwealth Federation to serve in that capacity. Simpson was born in Lancashire, England and immigrated to Canada at the age of 14. Never attending high school, Simpson worked selling newspapers at the age of 10 and then began working for a grocer at the age of 13 before moving to Canada where he worked in a tin factory before joining the printing trade. In 1892, Simpson was one of 27 members of the Typographical Union on strike against the Toronto News. The strikers, including Simpson, founded the Evening Star on November 3, 1892 as a strike paper. For ten years, Simpson served as the Star's City Hall reporter including nine years as the paper's municipal editor. He subsequently became editor of a labour newspaper.