Oliver Cromwell Carmichael, the University of Alabama’s 19th president, was president during a time of controversy. A native of Alabama, President Carmichael was aware that segregation was a deep-rooted tradition in the South, and, having worked in New York, he was aware of the progressive liberal ways of the North. President Carmichael found himself in the middle of these two groups, trying, but unable, to please both. On February 1st, 1956 the University of Alabama admitted its first African American student, Autherine Lucy. Within a week the University dismissed her because riots protesting her enrollment were increasingly violent. This would be the beginning of the University of Alabama becoming the symbol of Southern resistance to integration and defiance of the law. President Carmichael was a cultured, modern, and highly experienced educator and administrator in the world of higher education, yet he failed as president of the University of Alabama, and more important, he failed at desegregating the university when he was given an opportune chance. This study explored President Carmichael’s career in higher education and the leadership traits he did and did not possess. Using historical and archival research, the purpose of this study was to examine President Carmichael’s personality, relationships, professional behavior, and the context that surrounded his presidency at the University of Alabama in order to better understand the reasons behind the choices he made.