This paper challenges Dunn's framing of the early Caribbean and the emergence of slavery as "beyond the line" of English laws or justice or even social norms. It situates his claims within a longer and more elaborate historiography that portrays slavery as emerging within colonies themselves and via the actions of independent colonists. Then it challenges the assumptions of that framing by investigating the extent of English involvement in their empire, via imperial officials and policies including war and treaties and legal strategizing. Exploring the connections between different colonies amid the early legal and political uncertainty during the first decades of English settlement in the Americas illuminates how and why imperial support for slavery was crucial to its development.