At the beginning of the 19th century, there were only five medical schools in America. The Medical Department of Transylvania University in Lexington, Kentucky, was the first in the West; however, it had few students or faculty until it was restructured in 1815. In 1817–1818, three of its faculty members (Benjamin Dudley, Daniel Drake, and William Richardson) quickly developed a highly dysfunctional relationship. Dudley tried to have Richardson fired, with Drake blocking this. Drake then criticized Dudley's performance of a coroner's autopsy, resulting in both parties publishing derogatory comments about each other. Dudley then challenged Drake to a pistol duel but Drake, not believing in dueling, declined. Richardson, wanting to defend his friend's honor, accepted the challenge and was mortally wounded in August 1818. Dudley, a prominent surgeon, saved his life. Both Dudley and Richardson were important Kentuckian Freemasons and the brotherhood felt compelled to punish them for un‐Masonic behavior. Drake left and started his own medical school in Cincinnati in 1819, in direct completion with and destabilizing Transylvania's school. This saga is dissected in the context of the bizarre history of dueling as part of the Code of Honor by which gentlemen in the Old South often resolved their differences. The essay analyzes the autopsy dispute and reviews politics within the medical school, the University, and newer competing medical schools. Transylvania's medical school was recognized as one of the best in the US during the first half of the 1800s, but by 1859, it had permanently closed its doors. Clin. Anat. 32:489–500, 2019. © 2019 Wiley Periodicals, Inc.