Reconstruction legislators faced the uncomfortable yet broadly acknowledged fact that the U.S. Constitution had countenanced slavery. The Fourteenth Amendment set out to guarantee and secure civil freedom through the reassertion of the U.S. Constitution, yet its expansive possibilities proved short-lived. Anti-Chinese ideologues and nativists challenged birthright citizenship and advanced new legislation restricting legal entry into the United States. The 1882 Chinese Exclusion Act, the nation’s first raced immigration and naturalization ban, helped stabilize the meaning and value of citizenship as the federal judiciary began narrowing the scope of the Fourteenth Amendment. By the end of the century, the Chinese Exclusion Acts and federal rulings on Chinese immigration cases completed the redefinition of the Asiatic as the categorically excluded. Among the earliest Asian American writers to publish in English, Wong Chin Foo and Edith Maude Eaton (Sui Sin Far) produced a wide-ranging body of journalism and short fiction that addressed public anxieties over “contraband Chinese.” The criminalized “illegal immigrant” remains a ready foil for the citizen, shoring up fantasies of national belonging as our civil liberties face increasing erosion. The writers discussed in this chapter offer us a unique vantage on this conflicted and evolving history of U.S. citizenship.