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This paper presents a critical analysis of the last 250 years of Cuban political history, from a perspective of its integration in the Spanish Caribbean. We discuss how the traditional Cuban political and ideological intolerance has contributed to the creation of an inefficient model of regime succession that has taken the country to its current stage. We present and examine several national and international conditions that we believe are necessary to achieve a peaceful transition toward an open and pluralistic system. We analyze and compare the transitions in Brazil, Mexico and Spain. And we draw several conclusions that may be applicable to the Cuban case. [ABSTRACT FROM AUTHOR]