The concept of freedom, specifically the freedom of a population to dictate the outcome of its own governance, is central to American democratic discourses. Within the greater American historical myth, freedom and democracy are co-constitutive, the discussion of one implies the other (Drury 2014, Ish-Shalom 2008, Nau 2008, Noon 2007). So, it is of little surprise that it features heavily in Reagan’s speeches throughout his presidency. The concept is deeply ingrained within the American population, making it a strong identifier when addressing his constituents. Freedom and democracy are linked with one another and the meta-narrative of democracy is often related to the U.S. population through the sub-topic of freedom. Further to this, the utility of freedom for the rest of the western world is inherent in their various democratic foundations. This chapter traces the use of the freedom trope by Reagan and how this filtered into congressional discussions, outlining how this subtext was implemented in order to relate the President’s broader foreign policy meta-narrative of democracy. Through this deconstruction the manner in which both media outlets and movies interact with this trope will be displayed. In doing so the discursive structure that binds these sites of production to one another will be demonstrated. This chapter provides a breakdown of the freedom trope’s initial emergence in the production phase, its transformation into the sustaining phase, and discussion of the processes by which it evolves into the challenge phase.