Can there be genuine freedom of choice? This paper takes into account competing versions of freedoms and liberties from the Western tradition. There are competing accounts because of the variegated approaches to understanding freedom. There are also various advantages and disadvantages to these varieties of conceptual freedom. If it were possible to place these on a linear scale, there are choices that lie on the right-wing and, at the other extreme, on the left-wing. These propagandist notions of freedom pose serious consequences for the actual choices offered as well as the choices that are eventually made. The paper examines the key arguments made by the most important philosophers of democracy and freedom in modernity. The paper questions whether anyone ought to bother about freedom in the first place. The paper concludes with the major articulations of freedom from both normative and positive political theory.