Although socially and culturally Milton and Winstanley perhaps appear improbable bedfellows, this essay begins by reviewing possible interconnections through the intermediary context of the London radical scene in the mid-1640s. It goes on to consider their contrasting achievements as arguably the most creative and innovative interpreters of the Edenic myth in the early-modern literary tradition. Winstanley’s ‘man called Adam, that disobeyed about 6000 years ago’ and Milton’s ‘Offspring of heaven and earth, and all earth’s lord’ go head-to-head in a comparative analysis designed to refine our understanding of the heterodoxy of both authors.