The article explores the ambitions, challenges, successes and perceived failures and disappointments of the policies pursued by the Democratic administrations of President Barack Obama, with particular focus on Honduras, Mexico and Colombia. The article notes the eloquent and optimistic rhetoric of Obama, in his first presidential campaign and in the early days of his first administration, commitments to significant change in U.S. policy toward Latin America. In contrast the record of the first five years of his administrations have witnessed the continuation of policies which are difficult to distinguish from those of his predecessor. The article also notes the general decline in U.S. influence in the region. There has been insignificant change in Cuban policy, save for a liberalization of family travel to Cuba. His administration implemented the controversial Free Trade Agreement with Colombia which his own party leaders had long opposed. He has maintained the funding levels of the equally controversial Plan Colombia which began under Bill Clinton, and he has continued to adhere to a largely Republican agenda on border security with Mexico.