Crawford was elected as a Toronto District School Board in 2003, representing Scarborough Southwest. During his seven-year tenure, he was variously appointed as Co-chair of the Board, Chair of Facilities Management, and Chair of Negotiations. Crawford, who was previously a professional artist and part-time musician, is an advocate for arts and culture and was involved in funding increases for the arts. Crawford ran as a candidate for the
Progressive Conservative Party of Ontario during the
2007 Ontario general election, but was defeated by
Liberal candidate
Lorenzo Berardinetti. He was elected to the
Toronto City Council in the
2010 municipal election to succeed
Brian Ashton representing Scarborough Southwest, and was
re-elected in 2014. As a city councillor, Crawford served as the Budget Chief from 2014–2023 and served on numerous committees including Budget, Planning and Growth, Economic Development, and the Executive Committee. Crawford resigned his seat as city councillor in 2023 to run as a candidate for the Progressive Conservative Party of Ontario in the
Scarborough—Guildwood provincial by-election. He was defeated by Liberal candidate
Andrea Hazell. In addition to his elected positions, Crawford has served on the boards of the East Metro Youth Centre, the
Harbourfront Centre, the St. Lawrence Centre for the Performing Arts, the
Toronto Centre for the Arts, the Toronto Arts Council, and as interim chair of the
Sony Centre for the Performing Arts. He has also chaired the
Mayor's Task Force on the Arts, the Theatres Working Group, and co-chaired the Film Board. ==Election results==