This essay, a slightly revised version of the distinguished historian address presented to SHGAPE in April 2013, suggests that millennial learners are oftentimes inadequately introduced to the African American experience during the Progressive Era, a period that historians of the black past, sampling from Rayford W. Logan's 1954 opus, customarily call “the Nadir” or “the lowest point” in the African American struggle for social justice. When discussing the Progressive Era, normative U.S. history textbooks at high school and college and university levels tend to relegate blacks to the margins of cultural and historical change, minimize lynching and other forms of anti-black violence that characterized the period, and endorse the archaic W. E. B. Du Bois–Booker T. Washington dichotomy of black leadership at the expense of oversimplifying and even denigrating Washington's accomplishments and legacy. On the other hand, specialized African American history textbooks and monographs equip their readers with critical interpretations that challenge what historian Manning Marable called the “master narrative of American history.” In this essay, I offer my thoughts on these subjects and propose some basic suggestions for more effectively teaching, problematizing, and thinking about the African American experience during the complex Progressive Era.