This article examines the complicated decisions parents make when they decide to raise critically conscious children. The article argues that critical parenting in US society is often analogous to the Greek myth of Sisyphus. Using Critical Race Parenting, Critical Race Theory, and Critical Whiteness Studies, this critically interpretive parable looks to the election of Donald Trump as US President and the ways whiteness, patriarchy, sexism, xenophobia, ableism, and racism function in social, cultural, economic, and educational spheres. This parable tells the story of Sue Libertad and analyzes how parenting in the era of Trump is Sisyphean. This concludes with a discussion of the importance of talking about race, racism, and heterosexism with our children, which disrupts whiteness, sexism, and patriarchy, and ultimately Trump and his administration.