This chapter discusses the interrelationships between Charles Brockden Brown’s writings and the historical forces of colonialism and empire. Brown’s novels, journalism, political pamphlets, and historiography explore the impact of US territorial and commercial expansion, the slave trade, political violence, and ideologies of racial difference on the development of the republican political experiment. Brown challenges the ideological divide between British colony and American republic. His writings register how colonialism was part and parcel of the Bildungsroman of a rising republic with imperial designs in North America. This political paradox marked the distinctiveness of Brown’s settler-national voice. Recently, scholarship attuned to the historical forces of colonialism and empire has reorganized the prevailing chronology of Brown studies. It is no longer widely accepted that Brown, after 1800, turned toward conservatism and abandoned aesthetic experimentation. The reception history of Brown’s later work now reads like one of his compelling, contradictory, unpredictable Gothic novels.