Within Paradise Lost are numerous themes of early European colonialism: Satan as an imperialist aggressor, Adam and Eve as peaceful settlers, and Eden as a literal New World. Dissecting these themes tends to beg the question whether John Milton supported his country’s colonialism or not. The duplicity in the poem’s colonial parallels suggests that what support Milton may have had was conditional; in the poem, Milton condones Adam and Eve’s colonialism, but not Satan’s. Satan’s colonialism may very closely resemble that of the Black Legend Spanish, but this paper will approach it differently. This thesis will suggest two colonial readings of Paradise Lost : the first, that Satan’s conquest of Eden resembles Oliver Cromwell’s conquest of Jamaica; the second, that Adam and Eve’s settling in Eden resembles the Puritan settling of New England. These two readings create two distinct models of colonialism as Milton understood them: an imperial model, and a settler model, respectively. Through historical examples and evidence from the poem, this paper will argue Milton’s support of the latter model in favor of the former, as well as examine his stakes in writing colonial literature.