The Cayman Islands are home to a world-leading offshore financial centre (OFC) and are the domicile for a significant number of hedge funds (Z/Yen Group Limited 2010). It is this position as an important financial centre that makes the Cayman case particularly interesting, because the outcome from any sovereignty game under play among the Cayman Islands, the United Kingdom (UK) and the European Union (EU) may produce externalities affecting other major financial centres and global finance more generally. This study casts light on the complex interplay over human rights and international taxation engaged between the postcolonial citizens of Britain’s imperial past in the Caribbean with a postmodern Europe.