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The world of blackface minstrelsy was one in which white actors tried on the bodies not only of black men but also of women. This chapter looks to interrogate Garber's relocation of power in black transvestism in the specific case of Jackson. This is done in the context of the prototype of Garber's transvestic figure: the transvested male 'wench' of blackface minstrelsy. Crucially, and in keeping with the minstrel tradition more broadly, the 'wench' was contradictory and notoriously ambiguous, and subjected to a whole host of different investments. In Jackson's version of transvestism this contradiction and ambiguity was equally defining so that, indeed, he could have been empowered, but certainly not entirely or univocally so. In this, the power of those around Jackson, his audience, is brought forth and the deconstructing effect of this on Jackson's ability to have been wholly empowered as Garber claims he was.