Cuba and Venezuela have historically been signaled as the two longest-lasting socialist revolutions and governments in the Western hemisphere. Much of their revolutionary theory has been based on the actions taken by the United States towards Latin America as a whole, as well as towards those two countries specifically. This can be most acutely perceived in the ways in which the leaders of these revolutions, Fidel Castro and Hugo Chávez, speak about the United States in relation to their own ideologies. Consequently, simultaneously studying these policies by the United States, Castro’s speeches, and those by Chávez provide evidence on how punishment and radicalization are closely related. Specifically, political sanctions have historically fueled the passion with which the sanctioned regime opposes its rival. Additionally, the punishment and radicalization on one revolutionary regime has informed the other revolutionary regime, in that the close ties between Cuba and Venezuela have been crucial to shaping some of Chávez’s rhetoric as well.