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This chapter focuses on two sets of letters from two black settlers to a white acquaintance and a former master in the United States: Samson Ceasar’s letters to Henry F. Westfall and Nancy Ann Smith’s letters to John McDonogh. By dwelling at some length with the speculative intricacies of these letters, the chapter elaborates not so much what concrete histories they describe as how they teach us about the ongoing, volatile concrescence of a free life. These letters prompt us to revise the nineteenth century’s most elaborate and influential speculative account of such a life, at the crossroads of mastery and servitude: that of G. W. F. Hegel.

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