A critical discourse analysis (CDA) was employed to examine judicial opinions in the United States and Russia on the free speech provisions in their respective constitutions. As a research perspective, CDA is designed to directly speak to social change, focusing on power, history, ideology, and language’s role as a social phenomenon in expressing values of individuals and social groups (Wodak & Meyer, 2001). Fairclough’s (2001) methodological approach to CDA was selected for its consistency and structure in examining societal issues in CDA; namely, a five-stage approach that includes: (1) focusing on a social problem that possesses a semiotic aspect; (2) identifying obstacles to addressing the problem through text as semiosis (in relation to his three-part model addressed above); (3) considering whether the social structure “needs” the problem; (4) identifying potential routes to overcome the obstacles, and (5) reflecting critically on the first four stages. This methodological framework was utilized in answering the following research questions: (1) What are the textual and constructive differences in the U.S. and Russian constitutional free speech provisions and judicial systems? (2) How do the differences in (1) affect the protection of individual speech rights? (3)What are avenues to protect or improve speech rights in the future? The results of this study manifested similar structures of power and methods of defending the courts’ authority, notwithstanding different cultural understanding of free speech and jurisprudential approaches.