In this thesis, I engage scholarship on Caribbean Indigeneity, archival construction, and intimate networks to explore shifting dynamics between Kalinago and English peoples in the seventeenth century Lesser Antilles. The central figure is Thomas “Indian” Warner, who operated as both an Indigenous leader and an English colonial governor until his murder, potentially at the hands of his half-brother, in 1675. I use depositions taken from a variety of English colonists during the investigation into Indian Warner’s death to reconstruct the familial networks that Warner fostered in a lifelong attempt to connect Kalinago and English peoples into a novel kind of society. I also seek to understand the process by which colonists shaped the dominant historical memory of Warner. I argue that Warner successfully drew groups of Kalinago and English into a shared intimate network, fostering a new Antillean Indigeneity, until the English rejected their inclusion in this network and violently disentangled themselves. Warner sought to meld the fluidity at the core of the Indigenous Caribbean and the networked ties underpinning European empire, using his hybrid position to produce stability through connection.