This chapter argues that Western border thinking emerges concurrent with early formulations of conquest and labor management. Tracing an arc that begins with Spanish philosopher Juan Maldonado and concludes with African philosopher Achille Mbembe, the chapter discusses the utility of borders to the concepts of self, property, and freedom. It further argues that such conceptual work of borders has also been challenged and reconceptualized by contemporary poets and novelists including, most famously, Gloria Anzaldúa, as well as Sandra Cisneros, Alfredo Aguilar, and Eric Gansworth (Tuscarora). Each of these attend to the ways borders serve as generators of revenue for states and as abjection machines, but also as places of habitation, as processes, and as dense horizontalities, rather than as fixtures on a nested hierarchy of scales.