In his quest to win the 2013 New York City mayoral election in the opening moments of the Black Lives Matter movement, Bill de Blasio emphasized his intimate proximity to blackness by way of his mixed-race family to signal his racially progressive politics. De Blasio’s access to what Cathy Cohen calls “third wave Black politics” allowed him to use his relationships with his son, Dante, and wife, Chirlane McCray, to secure a majority vote in a divided and diverse electorate. However, in centering de Blasio’s family in campaign advertising as a tool to express his “biracial cool,” the de Blasio campaign did not account for how both the mixed-race family and Black motherhood are historically fraught terrain in American history. McCray’s presence as a Black queer mother and founding member of the Combahee River Collective presented a challenge to de Blasio’s ability to control his family’s image and follow through on his message. Because he did not adequately attend to the activist histories of policy needs of the voter blocs his mixed-race family represented, the very same characteristics that made de Blasio a standout candidate were used to critique him, his campaign, and subsequently his 2020 presidential bid.