The rise of populist leaders like Trump certainly raises issues of leadership and effectiveness. The current populist moment may be one of “Cultural Backlash,” but there is also merit in resurrecting and assessing the work of Niccolò Machiavelli in evaluating Trump’s leadership and success. Would Machiavelli, with his emphasis on a “success ethic” and a studied moral indifference, rate Trump to be a “great prince?” This article analyzes Machiavelli’s role and contemporary relevance as well as what he might say about a leader like Donald Trump. Machiavelli offers one insight into a style of leader that exposes the dangers of ignorance allied with self-interest in a nationalist pose. Also, we can visualize (with Machiavelli’s help) a modern reconsideration of the dimensions of love, hate, and fear in 21st century leadership—especially among national populist leaders. This matters politically to us all.