Born in England, James “Jimmie” Simpson migrated to Canada at age 14. He began working in a tin factory, but his Sunday School teacher got him an apprenticeship as a printer. In 1892, he was one of 27 union printers on strike against the Toronto News. The strikers, including Simpson, founded the Evening Star as a strike paper. For 10 years, he was the Star’s city hall reporter and nine as its municipal editor. He became vice-president of the Toronto and District Trades Labor Congress of Canada.
Simpson was elected to the school board from 1905 to 1910, and got appointed to the Royal Commission on Technical Education. He ran for several offices as a socialist candidate, but lost. In 1914, however, he was elected as a controller on city council. In 1912, he became co-editor of the Industrial Banner, a weekly labour newspaper. During World War 1 and the 1920s, he was a leader of the Ontario Labour Party, for which he ran unsuccessfully in federal and provincial elections. From 1930-34, Simpson sat on the Board of Control again. The next year, he became Toronto’s first labour mayor, running under the CCF banner.