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The history of the Shields families of North and South Carolina, beginning with William Bryant Shields Sr. and Moses Shields respectively, offer dichotomous responses to American racial hierarchies over the decades. Generations of race mixing within the Shields family has its roots in the sons of Irish immigrants pursuing relationships with enslaved women. The one-sided nature of the power dynamic in these relationships takes on different dimensions in the lives of the mixed-race children of William Bryant Shields Sr. and the lives of Moses’ son, Henry Wells Shields, Henry’s slave Melvinia Shields, and her children. Both family lines take efforts to repress their black ancestry, one primarily through dilution through marriage and the other through a refusal of formal acknowledgement, which ironically enabled some of their children to flourish in African American society. The permeability of race can be gleaned through these two Shields family lines both in how they went about repressing their ties to enslaved black women and how these culminated in the present-day Shields descendants, Roseanne Cash and Michelle Obama.