This essay investigates the politics of cultural and territorial expansionism in the representations of miscegenation and cross-cultural hybridity, in Lyida Maria Child’s Hobomok (1824) and James Fenimore Cooper’s The Pioneers (1823). In Child’s Hobomok, in the early colonial period Mary’s seemingly radical choice of intermarriage with Hobomok, a native in Massachusetts, cannot transcend safety the taboo of crossing the racial/ethnic boundary prevalent in Mary’s and/or Child’s age. In terms of mutual acculturation between Hobomok and Mary, the author biasedly foregrounds that Hobomok is Europeanized rather than the other way around, which means crossing the boundary does not make white Americans’ identity unstable at all. Additionally, Child portrays Hobomok’s later renunciation of his marital status as an inevitable course prepared for a doomed Indian. Little Homomok, a hybrid progeny symbolizing the (imaginary) reconciliation between the two racial parties, eventually loses his Indian heritage. In The Pioneers, similarly, unifying myth in the formative period of the United States in provided not only in the symbolic miscegenation between Elizabeth Temple (a representative of white pioneers in newly-built New York) and Oliver Edwards (a symbolic descendant of the vanishing Delawares) but also in the hybridization of several figures like Natty Bumppo, Oliver, and Indian John Mohigan. However, it turns out to be a rhetorical gesture imaginatively solving some historical tension from the whites’ encroachments of Indians’ lands. As in the case of Hobomok, crossing the boundary in The Pioneers does not actually endanger white Americans’ identity in terms of blood and culture, which testifies the author’s valorizing of asymmetrical and hegemonical relationship between the two racial groups. More than that, Cooper’s portrayals of symbolic intermarriage between Elizabeth and Oliver elaborately pave way for rationalizing white Americans’ entitlement of Indians’ land. Besides, this essay identifies that Indianized Natty’s romantic impulse to escape from the restrains of the Eastern civilized world is weirdly converted into a pathfinder’s desire for westward expansion. Also, this essay examines how Natty’s ostensibly sympathizing attitude toward a degenerated Indian John is involved with expansionist rhetoric often employed by a lot of Jacksonian politicians who campaigned for Indian removal into the West. This study would help us to understand that Child and Cooper conceal and reveal simultaneously expansionist rhetoric in diverse ways, in conformity with their contemporary (mis) belief of Manifest Destiny, in spite of (or more precisely because of ) their construction of unifying “myth” between white Americans and Native Americans.