This research project identifies cultural limitations a local translator might face when dealing with the task of rendering political speeches. In an attempt to recognize and classify those aspects that might hinder understanding of political speeches, Critical Discourse Analysis becomes a valuable tool to ascertain the necessary background information about a text so as to develop a final proposal in the form of contextualized translation templates and contextualized translation recommendations. This work articulates the most relevant cultural elements, cultural references, and linguistics and rhetorical features of Donald Trump and Barack Obama’s inaugural addresses that might posit challenges to translators dealing with those political speeches. It provides a detailed analysis of the abovementioned aspects and offers guidelines for translators undertaking similar processes. It includes a set of templates that can be used to compare texts and two different renderings that portray the claims. Therefore, through establishing the basis for further En>Sp translations in the political field, this research highlights the importance of studying a source text before translating it into another language.