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In the seventeenth-century Chesapeake and West Indies, significant wealth acquisition and status promotion occurred largely among affluent, well-connected English migrants. But despite the optimistic claims of some promotional tracts, social mobility was rare among indentured servants, and only a very small minority of freedmen and freed-women rose to become wealthy planters, merchants, and colonial office-holders. Nevertheless, literary accounts of early colonial life often radically exaggerate the incidence and extent of servant mobility and describe plantation colonies as beset by uncouth upstarts and rampant status confusion. Drawing on an English tradition of antimobility rhetoric, such texts satirize risen former servants as ignorant, vulgar, and immoral, mere caricatures of the polite gentry they seek to emulate. In doing so, these satires obscure both the brutal suffering of colonial servitude and the extensive mobility frequently experienced by middling and elite migrants. But they also betray their authors’ ambivalent attitudes about the morality of English colonialism and the unchecked pursuit of gain it facilitated.