Matlow ran as the Ontario Liberal Party candidate in the 2002 Dufferin—Peel—Wellington—Grey byelection, losing against Progressive Conservative Premier Ernie Eves.

His father, Ted Matlow, was a federally appointed judge and his mother, Elaine Mitchell, was a retired high school teacher.

[1] He studied political science at Concordia University and attended L'École Internationale de Théâtre Jacques Lecoq in Paris, France.

[5] In 2002, at the age of 26, Matlow was asked by the Ontario Liberal Party to run as their candidate in Dufferin—Peel—Wellington—Grey in a by-election against Progressive Conservative Premier Ernie Eves.

[17][18] In a 2011 interview with BlogTO, he proposed contracting out garbage collection services and allowing unions to compete in the tender, citing frustrations during the 2010 strike.

He refers to the LRT as the "evidence-based" transit option, arguing that it serves more people within walking distance and would have been fully funded, instead of requiring the city to take on additional expenses for a subway extension.

[24] In February 2015, Matlow raised a number of administrative inquiries relating to ridership, the cost of cancelling the LRT project, as well as proceeding with a subway extension.

[26] In 2018, Matlow called for a judicial inquiry to investigate what he described as "dysfunctional" transit planning, citing lack of information and misinformation that was provided to council.

[27] At the beginning of the COVID-19 pandemic, Matlow became the first known Canadian politician to go into quarantine on March 9, 2020, after coming into close contact with a person who had tested positive for COVID-19.

[33][34] The second complaint was filed by Interim City Manager Tracey Cook, who Matlow claimed made a "decisions to omit facts".

The commissioner recommended that council dock 10 days of pay from Matlow due to “an escalation” of his misconduct and his history of breaching the code of conduct.

[36] In an interview with the Toronto Star, Matlow described his approach as "pragmatic progressive", and committed to improving city finances and services through cost savings and a property tax increase.

He has also said he intends to ask council to re-evaluate the plan to rebuild the eastern portion of the Gardiner Expressway, stopping its rehabilitation and replacing it with a less expensive boulevard option.