BackgroundFranklin Delano Roosevelt's fatal brain hemorrhage on April 12, 1945 provides an excellent platform for the study of the potential causes of one of the most famous headaches in history. ImpressionThe differential diagnosis of thunderclap headache, including hypertension and melanoma, is discussed, as are Roosevelt's health problems in the context of how serious diseases of our leaders can have a tangible effect upon historical interpretation. DiscussionA large body of evidence is presented in support of a probable cover-up of Roosevelt's health problems, perpetrated by his doctors and close confidantes. The necessity of challenging conventional thinking about the health of our leaders and the fundamental importance of understanding their health issues is also emphasized.