This chapter links leadership in the West to five major historical periods: Ancient Greece, Ancient Rome, the Renaissance in Europe, the Enlightenment, and the Industrial Revolution in Europe and North America. It also presents a synopsis of Machiavelli’s The Prince and its connection to a Western perspective on leadership. Major themes include: leader-centric individualism juxtaposed with transactional leadership based on the rule of law; pragmatic/utilitarian individual morality balanced by a secular code of ethics; and freedom of expression contrasted with a democratic community.