The three terms comprising the Obama and Trump presidencies provide an opportunity to understand the evolution of race-conscious education policy in an increasingly multiracial, unequal, and divided society. Through document review and interviews with civil rights lawyers, government officials, congressional staffers, and intermediary organization personnel, we sought to understand how Obama officials envisioned and changed the role of the federal government in fostering K-12 race-conscious educational policies and what mechanisms they used to advance priorities. We also explored changes Trump administration officials made to federal civil rights policies and through which institutional means. Our findings reveal through-lines between past and present political agendas and the methods for enactment. Obama’s interagency efforts to reinvigorate civil rights oversight and enforcement in education harkened back to the mid-1960s era of bipartisan cooperation around school desegregation. Yet the decades-long legal and policy retrenchment against civil rights advances made in the 1960s constrained further progress. Trump’s administration advocated for the privatization of public education through increased choice and opposed race-consciousness in education law and policy. The reshaping of the federal judiciary under Trump presents challenges for race-consciousness in the law for years to come. Recognizing these consistent through-lines and constraints will be essential for advocates and policymakers going forward.