This study examines Fidel Castro’s leadership emergence and style in Cuba with reference to the situation, goals sought, leadership process and the outcomes. The emergence of Fidel Castro was underpinned by the qualities he exhibited and significant popular support he enjoyed from different strata of the society. Transforming a pre-revolutionary corrupt, oppressive and discriminatory system by creating equal opportunities for everyone was the main objective of Fidel Castro’s led revolution in Cuba. Despite some efforts toward societal transformation, Cubans were divided over the achievements of the revolution. While some expressed positive views about Fidel Castro’s initiated socialism, others described it as a source of frustration. Findings reveal that the level of leadership effectiveness under Fidel Castro was largely attained through a variety of styles used to address different situations. The resilient abilities Fidel Castro shared with followers could enable socialist Cuba to survive the ColdWar and the post-Cold War eras.