Brandon began his career teaching at Jenner Academy in Cabrini-Green, then at Westinghouse College Prep. He later became an organizer with the Chicago Teachers Union, defending schools from privatization and expanding access to state funding. In 2018, Brandon was elected commissioner of the 1st District of Cook County, where he led efforts to pass the Just Housing Ordinance, prohibiting housing discrimination against formerly incarcerated people. He also collaborated with colleagues to secure legal representation for immigrants facing deportation and advance recognition of Indigenous Peoples’ Day. Brandon and his wife Stacie live in the Austin neighborhood, raising their children Owen, Ethan and Braedyn.