David Chase’s series The Sopranos (1999-2007) was a wildly successful and popular show which has attracted rich analysis from both critics and academics. However, what has not been adequately analyzed by scholars is the central role that race (specifically Whiteness and Whitening) plays within the series. By using theories of Whiteness (especially Sheshadri-Crooks’s idea of Whiteness as master signifier), Whitening, and racialization, this paper shows how ItalianAmericans’ history of racialization, oppression, and eventual Whitening and deracialization expresses itself in complex ways within the series. Specifically, this paper focuses on how the trauma of historical Italian-American oppression and racialization are a constant theme within the seemingly Whitened ItalianAmerican communities and relations portrayed in the series. This intergenerational trauma is considered in the context of historical developments in the Italian-American community and dialogue and plot developments within the series.