Activism Cressy has worked on various social justice issues, which traces back to high school when he spent a year in South Africa. Upon returning to high school in Toronto, he got involved in the anti-Iraq war movement and has since worked on anti-poverty campaigns in South Africa, literacy programs with First Nations communities in Northern Ontario, and worked with The Stop Community Food Centre. Cressy also supports
LGBTQ issues, volunteering for an LGBTQ organization while studying abroad in
Accra and supporting the
New Democratic Party's (NDP) call for a visa ban against legislators who passed anti-gay laws in Russia.
Federal politics Cressy ran for the
New Democratic Party (NDP) in a by-election seeking to represent
Trinity—Spadina in the
House of Commons following former NDP member of Parliament (MP)
Olivia Chow's resignation to run for
mayor of Toronto in the
2014 mayoral election. Cressy placed second, following winner
Adam Vaughan who previously represented Ward 20 on Toronto City Council.
Toronto City Council Following his defeat federally, Cressy ran and was elected in the
2014 municipal election in Ward 20 Trinity—Spadina, succeeding
Ceta Ramkhalawansingh, who was appointed interim councillor following Vaughan's resignation to run for MP. As councillor, Cressy has sat on the Toronto Board of Health (serving as chair), the board of directors for
Toronto Community Housing, the Parks and Environment Committee and the sub-committee on Climate Change and Adaptation. Cressy ran again in the
2018 municipal election in the newly formed Ward 10 Spadina—Fort York, which his old ward was amalgamated into. He was re-elected by one of the widest victory margins of any councillor in the city with 55.06 per cent of the vote. He resigned from city council, effective April 30, 2022, to accept an appointment as senior vice president for external relations, communications and real estate development at
George Brown College. == Personal life ==