The U.S. Cuba Relationship: Trying Something New

The U.S. and Cuba have an atypical diplomatic relationship that John Caulfield calls highly-emotional. Caulfield shares the fundamental disagreement between the U.S. and Cuban governments and urges the Cuban government to evolve in today’s ever-changing world.

Mr. John Caulfield is a retired career American diplomat now based in Jacksonville, Florida. Over the course of his career, Mr. Caulfield negotiated agreements with some of the most contentious governments in Latin America. In his most recent post, Mr. Caulfield served as Chief of Mission of the U.S. Interests Section in Havana, Cuba from 2011 to 2014. He achieved agreements on immigration, environmental protection, civil aviation and cultural exchange; championed the aspirations of ordinary Cubans to increase their political rights and economic opportunities in a difficult environment. Prior to assuming this position in September 2011, Mr. Caulfield served as Chargé d’ Affaires at the American Embassy in Caracas since July 2010. Mr. Caulfield is also former Consul General at the American Embassy in London. From 2002 to 2005 he was Deputy Chief of Mission at American Embassy in Lima, Peru. In a career spanning more than 30 years, Mr. Caulfield has held a variety of positions dealing with Latin America and Consular Affairs. He served as American Consul General in Manila, Philippines, and as Consul in Ciudad Juárez, Mexico. He has also directed the Office of Congressional and Public Affairs for the Department of State’s Bureau of Consular Affairs. Earlier in his career, he served in Washington as Country Affairs Officer for Argentina and Brazil, and overseas in Colombia, the United Kingdom, Portugal and Brazil. Mr. Caulfield is fluent Portuguese and Spanish, and continues to serve as a resource for organizations interested in Latin America. Having stood at the intersect of U.S.-Cuba relations, Mr. Caulfield has particularly valuable insight on fundamentals pertaining to the country’s regulatory landscape, as well as the future outlook on Cuban politics and steps towards opening the country up for trade.

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