This chapter attempts to do justice to the media exemplars’ rich stories by exploring this recurring humility-hubris dichotomy and by integrating it with the latest psychological research on these and related concepts. Both concepts, of course, have deep philosophical roots reaching back to the earliest writings. Humility has long been considered a key virtue among the classical Greek philosophers. It receives less attention than courage, temperance and the other virtues-not because it was perceived as less important but because humility’s role in human affairs was so obvious that it was considered to be a starting point for the virtuous life, not an end in itself. This point is emphasized in the Stoics’ opening chapter of The Art of Living: “Happiness and freedom begin with a clear understanding of one principle: Some things are within our control, and some things are not” (Lebell, 1995, p. 3). More recently, some psychologists have argued that the widely held theory of the “Big Five” personality traits should be amended as the Big Six, since research has suggested the existence of a separate, identifi able “Honesty-Humility” trait that is distinct from Agreeableness, Openness to new experience, Extraversion, Neuroticism and Conscientiousness (Ashton & Lee, 2005; Exline & Hill, 2012). And business researchers are increasingly refuting the relevance of the headstrong, larger-than-life ideal of the corporate executive glamorized in the popular press. Instead, they argue that a close look at the characteristics of nearly all business leaders who have moved their companies from good to great reveals a common, essential yet often-overlooked quality: humility (Collins, 2001; Morris, Brotheridge & Urbanski, 2005; Vera & Rodriguez-Lopez, 2004). This quality is encapsulated perfectly by one unassuming company chief, who over his 20 years as CEO outperformed all others in his industry yet never was the focus of a Wall Street Journal profi le, said at his retirement, “I never stopped trying to become qualifi ed for the job” (Collins, 2001, p. 138).