James "Jimmie" Simpson (1873 – September 24, 1938) was a British-Canadian trade unionist, printer, journalist and left-wing politician in Toronto, Ontario.

The strikers, including Simpson, founded the Evening Star on November 3, 1892, as a strike paper.

Simpson played a leading role in opposing Communists in the Labour Party.

They then formed the Toronto Labour Party, which explicitly excluded Communists from membership.

The other papers and both the Conservative and Liberal parties supported Simpson's opponent, Alderman Harry W. 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.