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Since the United States antebellum era, abolitionists, scholars, social reformers, educators, and political leaders have grappled with the Black community’s social, political, and economic progress. Consequently, several proposed solutions yielded creditable results, while other solutions stifled upward socio-economic mobility. Respectively, in the late 19th and early 20th century, two prominent figures, W.E.B. DuBois, a sociologist and historian and Booker T. Washington, an educator each proposed ideas for solving the Black community’s political, social, racial, and economic problems, with each positioning “education” as the solution. Drawing on perspectives and experiences of Black students attending a northeastern predominantly white institution and engaging with critical race theory, Black educational criticism, and historical/comparative analysis, this study revisits DuBois’, and Washington’s arguments to interrogate their applicability and examine the current state of Black education in the U.S. Lastly, we offer strategies for advancing Black education to maximize the Black community's educational, social, and economic progress.