November 22, 2013 marks the fiftieth anniversary of the assassination of John F. Kennedy (JFK), an event that continues to spark interest to this day. In this paper, James G. Blight and janet M. Lang examine JFK’s cautious skepticism — his “Black Swan logic”— which he used to scrutinize the potentially disastrous consequences of US military intervention. In doing so, JFK met with tremendous protest from his hawkish advisers — but a life of debilitating back pain, near-death experiences and barely controlled Addison’s disease gave him the steely resolved to trust his instincts, against the better judgment of doctors, generals and political advisers. JFK’s black swan logic helped him to avoid his hawkish advisers’ forceful attempts to bring the United States into conflicts that would have quickly escalated into nuclear war. Shedding new light on his misunderstood behaviour during an era of nuclear uncertainty, Blight and Lang conclude that JFK’s skeptical, cautious approach is as indispensable now as it was during his presidency.