Monday, February 23, 2026

James Simpson: The Story of Toronto’s “Most Persistent” Mayor

Life is an extraordinary thing, writes torontoyes. What seems impossible to some is entirely achievable for others. This applies to the well-known saying that “you can’t sit on two chairs at the same time,” implying it’s impossible to succeed in multiple fields simultaneously.

However, James Simpson proved otherwise. He managed to build a brilliant career as both a journalist and a politician. His success culminated in his election as the mayor of Toronto in 1935.

With references to thecanadianencyclopedia.com, we delve deeper into the journey of James Simpson.

Early Life

James Simpson was born in England. At the age of fourteen, he moved to Canada. High school education was not part of his path, and as a teenager, he worked to support himself. He began by selling newspapers and later found employment at a tin factory.

Journalism

In 1892, Simpson joined the Typographical Union, becoming a member during a strike against the Toronto News. On November 3, 1892, Simpson and other strikers founded the Evening Star, a strike-based newspaper.

For ten years, Simpson worked as a Star City Hall reporter and later served as a municipal news editor.

In 1900, Simpson founded the Literary and Debating Society, becoming its president.

Political Beginnings

Simpson eventually grew interested in politics. Initially, he led labour unions, later becoming vice-president of the Toronto and District Trades and Labour Council.

From 1904 to 1936, Simpson also served as vice-president of the Canadian Trades and Labour Congress.

Election Attempts

As a socialist labour politician, Simpson ran as a candidate in the 1902 elections, supported by the Socialist Party of Canada.

He continued his attempts during the 1905 provincial elections and the 1906 by-elections. Despite repeated failures, Simpson remained undeterred.

In 1908, Simpson ran for Toronto mayor in the municipal elections but was once again unsuccessful.

Council Membership

In 1914, Simpson was elected to Toronto’s Board of Control, receiving the highest number of votes.

He later returned to the Board of Control from 1930 to 1934.

Departure from the Labour Party

Simpson was a prominent leader of the provincial Labour Party, running for Parliament on multiple occasions but never securing a victory.

He played a key role in opposing communists within the party. When communists convinced the Labour Party to withdraw Simpson’s nomination in the 1927 elections, he and his supporters immediately left the party. This departure contributed to the party’s eventual collapse.

Mayor of Toronto

In the 1930s, Simpson joined the provincial Cooperative Commonwealth Federation (CCF).

In 1934, he ran for Toronto’s Board of Control as a CCF candidate and was elected, laying the groundwork for his mayoral campaign in 1935.

The Toronto Daily Star was the only newspaper that supported Simpson, while other publications endorsed his opponent.

Despite this, Simpson’s personal popularity helped him win the election, making Toronto the largest North American city to elect a socialist mayor.

As mayor, Simpson supported the campaign to boycott the 1936 Summer Olympic Games held in Nazi Germany.

Sudden Death

In 1938, Simpson’s life was tragically cut short when his car collided with a streetcar.

Photo: Wikipedia

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