Two years have passed since the City of Ottawa declared a housing and homelessness emergency on January 29, 2020; yet very little progress has been made toward building more affordable housing. One of the epicentres of local debate around affordable housing and urban social change has been the Heron Gate neighbourhood, a racialized, working-class community just south of the downtown core. In September 2021, Ottawa city council approved an Official Plan Amendment (OPA), submitted by property owner Hazelview Investments (a financialized real estate firm), to demolish 559 (more) dwellings and build over 50 new apartment buildings in Heron Gate. In 2016 and 2018, the landlord demolished over 150 townhouses, displacing hundreds of racialized families, including over 200 children. The OPA included a community benefits agreement based on the Conference Board of Canada’s community wellbeing framework. It offers affordable units in the new apartment as well as a commitment to not displace any more people from the neighbourhood. The agreement is championed as a first-of-its-kind agreement in Canada, in the absence of any legal mechanisms compelling the landlord-developer to do so. While different politicians, planners, and community groups have taken credit for negotiating the agreement, it was the organizing efforts against mass eviction by the Herongate Tenant Coalition in 2018 that caused the landlord to pivot, rebrand, and rethink its approach to redeveloping the neighbourhood. The Coalition opposes the agreement, deeming it a “framework for social destruction.” Rather than engage at the municipal level, the Coalition is seeking justice at the Human Rights Tribunal of Ontario (HRTO), including a right to return for those displaced from the neighbourhood, with the ultimate aim of halting future evictions. Using a political activist ethnographic approach, this research examines strategies over housing justice and tenant organizing through an examination of the OPA and HRTO cases.