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Nagel’s (1998) conceptual application of R.W. Connell’s (1995) hegemonic masculinity to nationalism, allows for scholars to unveil how portrayals of national “others” may rely on constructing “otherness” through contrasting race, class, or sexualized masculinities. Previous research shows that portrayals or descriptions of gendered “others,” have provided support for controlling, managing, punishing, or even undermining other nations and has implications for international relationships and treatment of immigrants and diaspora. This work intends to extend research that examines the connections of masculinity and nationhood through examining how Cuba, particularly its leadership is portrayed in the United States media. The author explores representations of Cuba, specifically Cuban men, using a textual analysis that includes 793 articles from 1959-2010 in Time and Newsweek. The author finds that these articles predominately emphasize the deficiencies of Cuba as a nation, through portraying Cuban men, specifically its leadership, as having “ineffective masculinity.” These narratives suggesting that Cuban men are (a) motivated by anger, violence, or idealism; and (b) illegitimate leaders through illustrating inadequacies in their profession and physicality. The comparisons drawn between the United States and Cuba illustrate how this “ineffective masculinity” is simultaneously tied to racialized notions of masculinity as well as a discourse of Cuba, as a nation, as a problem for the United States. These findings have implications for how Cuba is “imagined” by people in the U.S., future international relations between the U.S. and Cuba, and stereotyping of Cuban masculinity for Cubans both within and outside the U.S.