Introduction <p>Evolving demographic trends in the USA have prompted stakeholders to demand a healthcare workforce that reflects the general population. Despite improvements in gender representation in medicine and anesthesiology, Black and Hispanic trainees remain underrepresented. As today’s trainees become tomorrow’s leaders, this disparity threatens to perpetuate minority underrepresentation in anesthesiology leadership roles. Previous assessments of anesthesiology leadership overlooked crucial roles involved in the residency selection process, such as anesthesiology chairs and program directors (PDs), which significantly influence the specialty’s demographics. We analyzed the racial, ethnic, and gender distribution of these key “gatekeeper roles” to understand the potential root causes of minority underrepresentation in anesthesiology leadership positions.</p> Methods <p>This was a cross-sectional study of anesthesiology residency and fellowship programs available on the Fellowship and Residency Electronic Interactive Database Access (FREIDA) website. We extracted demographic data (gender, race, and ethnicity) of anesthesiology chairpersons, residency program directors, and fellowship program directors as reported on the FRIEDA website or from other online sources (department website or Google search). Three independent reviewers extracted demographic data, and an additional reviewer assisted with resolving demographic assignment conflicts when necessary.</p> Results <p>There were 603 anesthesiology faculty leaders from 171 academic anesthesiology programs of whom 145 were departmental chairs, 169 were residency PDs, and 289 were fellowship PDs. Overall, only 34% (<i>n</i> = 205) of these leaders were women. Departmental chairpersons were predominantly White (85.5%), with minimal representation from other racial or ethnic groups. Similar racial, ethnic, and gender underrepresentation was observed among residency and fellowship program directors (PDs) except in pediatric anesthesiology (women = 51.8%).</p> Conclusion <p>Considerable racial, ethnic, and gender inequities were identified in crucial leadership roles in academic anesthesiology. These findings suggest an urgent need for targeted actions to ensure equitable representation, particularly in positions that influence residency and fellowship selection processes, which ultimately determines the demographic composition of anesthesiologists in the USA. Promoting diversity in leadership roles can help ensure a more equitable and representative healthcare workforce, which is essential for improving patient care and fostering innovation. </p>