In Democracy in America, Alexis de Tocqueville argues that passions for both equality and liberty constitute the chief attributes of liberal democracy. In the same century, Karl Marx and Friedrich Engels –followed by Lenin in the 20th century– contend that history is chiefly characterized by the conflict between those who own the means of productions and those who don’t –those who produce. In Beyond Good and Evil (BGE) and in On the Genealogy of Morals (OGM), Friedrich Nietzsche describes the whole of history as a permanent bipolarity between the strong –committed to the master morality of good vs. bad– and the weak –committed to the slave morality of good vs. evil. Michael Oakeshott, in The Politics of Faith and The Politics of Scepticism, suggests that, since the fifteenth century, modern politics can be characterized by two –logically opposite and yet practically complementary– styles of politics: the politics of faith and the politics of scepticism. Although they disagree on the characterization of the poles themselves, all four philosophers describe politics as a bipolarity: a dynamic between two poles. In this paper, I shall attempt to describe –and then reflect on– the dynamics of bipolarity in these four major works of political theory. Six sets of questions inform the essay. First, was there ever a time in which the political poles identified by the author were either nonexistent or different from the currently predominant or ultimate ones? If so, then why and what were the characteristics of that time? Second, what characterizes the political poles? Are the apparent poles more complicated than what meets the eye upon a first reading? Does the author reveal dimensions, levels, or different incarnations of the poles, or in fact more than two poles? Third, are the characteristics of the poles altered in any way by either political actors, or by way of their confrontation or interaction with one another? If so, how? If not, then why not? Fourth, does the identified bipolarity spontaneously create a political equilibrium or evolve into another, or is intervention required to produce an equilibrium or evolution? Fifth, if the latter, does the author recommend such intervention? Does the author give a normative teaching or assess the identified poles? Sixth, is the bipolarity theory valid? Does it accurately describe politics? The paper opens with the discussion of the first two sets of questions –i.e. the characterization of politics by Tocqueville, Marx, Nietzsche, and Oakeshott. The second section focuses on the intricate dynamics between the poles and on the mediation occurring between them –i.e. the third and fourth sets of questions. The fifth sets of question –i.e. whether the author gives a descriptive or a normative teaching– informs the third section of the paper. In the conclusion, I attempt to offer a personal view to the final question –i.e. the validity of the bipolarity theory offered by the four philosophers– and try to answer it in the Belgian federal context.