The purpose of this dissertation project was to examine comparative promotion and career processes of men and women prior to and during U.S. accredited allopathic medical school deanships. This study assessed the relationship between gender and the various career progression variables and service factors of medical school deans appointed between 1980-2006. The problem of practice was that despite the increases in the percentages of women medical school graduates, faculty, and administrators, the percentage of women who ascend to the deanship is still very low. The findings from this study show that while the number of women U.S. medical school deans has increased throughout the 26 year time period analyzed, the overall percentage of women deans is still low and fails to keep pace with the increase in the percentages of women in academic medicine. The analysis of the data for this study showed that there was a relationship between gender and several of the career progression variables and service factors included in this study—notably that women deans obtained their doctorates from lower NIH-ranked schools, they had more business-related advanced degrees, they took longer to be promoted to full professor, they were appointed to first deanships at lower NIH-ranked schools, and they had shorter durations as dean. Knowing more about deans and how they ascended to deanship positions may explain why there are so few women who have become U.S. medical school deans. By knowing more about women and men deans, medical institutions and others interested in the advancement of women to senior leadership positions will be in a better position to address the problem of so few women who are U.S. medical school deans.