Twain’s Adventures of Huckleberry Finn and Puddn’head Wilson portray black characters’ identity shift in a slaveholding society. In the first work, Jim, a black slave, has his status shifted to a free person. In the second, Valet de Chambers, equally a black but a free person, undergoes a change of his status to a slave. Both characters suffer haunting trauma in the process. Through the prism of New Historicism, this essay explores the shift of identity in both novels and uncovers different kinds of trauma these characters undergo. The essay is structured around three parts. After contrasting both novels’ plots, it highlights a happy identity shift in Huckleberry Finn before addressing a sad one in Pudd’nhead Wilson.