The publication of the Flexner Report in 1910 had an immediate and enduring impact on the training of African American physicians in the United States. The Flexner Report's thesis, "that the country needs fewer and better doctors," was intended to normalize medical education for the majority of physicians, but its implementation just 48 years after the Emancipation Proclamation obstructed opportunities for African Americans pursuing medical education and restricted the production of physicians capable of addressing the health needs of a nation that would grow increasingly diverse across the century.This article provides a working definition of structural racism within academic medicine, reviews the significant physician workforce diversity initiatives of the past four decades, and suggests the most successful of these possess strategies common to addressing structural racism (community empowerment, collaboration, clear and measurable goals, leadership, and durable resources). Stymied by popular ballot initiatives, relentless legal challenges, and dwindling funds, current and future efforts to increase diversity in medicine must maintain a focus on addressing the active remnants of structural racism while they build on the broad benefits of diversity in education and medicine. Despite creative and tireless efforts, no significant progress in expanding diversity within the U.S. physician workforce can be made absent a national effort to address this enduring barrier in the collective social, economic, and political institutions. The centennial of the Flexner Report is an opportunity for the academic medicine community to renew its commitment to dismantling the barriers to diversity and improving medical education for all future physicians.