This thesis explores the relationship between British colonial influence and Lesbian, Gay, Bisexual, and Transgender (LGBT) rights in the Caribbean. Comparing the Cayman Islands, a British Overseas Territory, and Jamaica, an independent former colony of the United Kingdom, the situation for LGBT people is evaluated. While Jamaica has serious abuses and a concerning situation for the human rights of LGBT people, the Cayman Islands’ LGBT community’s position is far less concerning. Owing to its continued connection to the United Kingdom of Great Britain and Northern Ireland, the Cayman Islands’ LGBT rights situation is much less dire. Through British influence via funding of human rights initiatives, the use of orders-in-council to alter loca...