Printing trade and journalism

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.^[2] For ten years, Simpson served as the Star's City Hall reporter including nine years as the paper's municipal editor.^[1][3] He subsequently became editor of a labour newspaper.^[4]

In 1900, Simpson and eight others founded the Ruskin Literary and Debating Society. He served as its first president. Today, it is Canada's oldest debating society.^[5]

Labour leader

Simpson went on to become a labour leader and was the vice-president of the Toronto and District Trades and Labour Council at the turn of the century and also served three terms as vice-president of the Trades and Labour Congress of Canada between 1904 and 1936.

Labour Party

1932 election ad for Simpson

As a socialist labour politician, he ran in the May 1902 Ontario election in Toronto. As a candidate for the newly-formed Socialist Party of Canada, he ran in Toronto North in the 1905 Ontario provincial election and in a 1906 provincial by-election in Toronto and in the 1908 provincial election, all unsuccessfully.^[6]

He was elected and served as a Toronto school board trustee, 1905–10.

He ran for mayor of Toronto in the 1908 Toronto municipal election as a Socialist but was not elected.^[7]

He was elected to the Toronto Board of Control in 1914 with the highest vote total ever given a candidate up to that time^[1] and sat on the Board of Control again from 1930 to 1934.^[8]

He was one of the co-leaders of the Ontario Labour Party (Ontario section of the Canadian Labour Party) in the 1920s and a Labour candidate for the House of Commons of Canada in Parkdale in the 1921 Canadian federal election, in Toronto Northwest in 1925 and 1926 Canadian federal elections but was unable to win election to Parliament.

Simpson played a leading role in opposing Communists in the Labour Party. After Communists convinced the party to withdraw its nomination of Simpson as its candidate for Toronto city council's Board of Control in 1927, Simpson and his supporters quit the party leading to its collapse. They then formed the Toronto Labour Party, which explicitly excluded Communists from membership.

Mayor

In the 1930s, he became a leading member of the Ontario CCF. In 1934 he ran as a CCF candidate for the Toronto Board of Control and was elected which set the stage for him to run for Mayor of Toronto in the 1935 municipal election. The only one of the city's newspapers to support him was the Toronto Daily Star. The other papers and both the Conservative and Liberal parties supported Simpson's opponent, Alderman Harry Hunt and accused the CCF of being anti-British and under Communist influence. Percy Parker, a leading Liberal, declared on the radio that "the bells of Moscow will ring when Simpson is elected mayor."

Simpson's personal popularity and the organization put together by the CCF and the trade union movement was enough to elect him making Toronto the largest city in North America to have elected a socialist mayor. As mayor, Simpson supported the campaign to boycott the 1936 Summer Olympics being held in Nazi Germany that summer.^[9]

Religion

Simpson was a Methodist and Christian socialist who became active with the Epworth League movement at the age of 16 ultimately becoming president of the Epworth League Toronto Conference. He also served as president of the Toronto Methodist Young People's Union and the Toronto Methodists' Cycling Union.^[1] Simpson was intensely anti-Catholic which cost him the support of the Toronto Star. When he ran for re-election as mayor in 1936 this contributed to his defeat.