This study asks if Black mayors’ individual and collective responses to George Floyd’s killing were qualitatively different than mayoral reactions to the deaths of Michael Brown and Freddie Gray. Specifically, I examine whether Black mayors rejected the “timeworn” tradition of respectability politics in favor of a new paradigm in 2020. I also consider the characteristics of mayors, cities, and media that may explain this change. My original dataset includes 232 public statements issued by 31 Black mayors during either the Obama administration (2014–2015) or Trump administration (2020). I find that the cohort of Black mayors leading large cities during Era 2 were demonstrably less likely to activate respectability politics when talking about Floyd’s murder than their predecessors. I discuss the implications of these observations considering the political climate mayors are confronting at the time of writing, around the 2-year anniversary of Floyd’s death.