This book traces American engagement in the English-speaking Caribbean from the eighteenth to the twenty-first century, and is the first to examine the policies of Presidents George W. Bush, Barack Obama and Donald Trump in this context. Focusing on The Bahamas, Jamaica, Trinidad and Tobago and Guyana as case studies, the book describes the growth of the English-speaking Caribbean and highlights American interest and foreign relations in this region from European discovery up through the post-9/11 era to today (1492-2019). The book demonstrates the unique relationship between America and the former British colonies, shedding light on U.S. foreign policy with the Caribbean in general and at a bilateral level with the four selected countries, providing a useful survey for students, scholars, diplomats, policymakers, governments officials, and anyone interested in gaining a better understanding of U.S. – Caribbean relations.