This paper aims to explain the Reopening of United States Diplomatic Relations with Cuba under the Barack Obama administration. Barack Obama's decision to normalize relations with Cuba was interesting to analyze. United States relations with Cuba which has a dark history, which later with the election of Obama as President of the United States carved a new history. Where Obama reopens diplomatic relations with Cuba. This paper will explain Obama's perceptions that are influenced by Obama's values, beliefs and knowledge both from Obama's personal life and Obama's life experience as a political activist. In his administration, Obama has a 180 degree different way with his predecessors, Obama is more of a government that is soft power than hard power in running his government. Obama no longer views Cuba as an enemy, the state sponsoring trorism, an anti-American country, changes under his leadership. Obama saw Cuba prospectively invited to cooperate under the leadership of Raul Castro.