This chapter focuses on the legalization of media censorship in Cuba at the end of the 1950s and the government’s transformative interpretation of morality and decency in entertainment programming. Between 1957 and 1958, as the Ministry of Communication regulated sexual content on television, the office also targeted material perceived to challenge the political status quo.  Government officials claimed that these regulatory measures were intended to protect Cuba from communist threats, but they also came at a moment in which U.S. media were regularly questioning Fulgencio Batista’s dictatorship.  By reporting on Fidel Castro and the 26th of July Movement soldiers, the U.S. began both to uncover Batista’s oppression while, at the same time, depicting Castro as a hero of the people. This U.S. mediated imagining of the rebellion and its maximum leader was prominent in the 1957 CBS documentary, Rebels of the Sierra Maestra: The Story of Cuba’s Jungle Fighters, the first television program devoted to Cuban revolutionaries. Rebels of the Sierra Maestra served as a preamble to some of the televised narratives utilized by Fidel Castro and his government after the triumph of the Cuban Revolution.