In this article, I interrogate the exhaustive “inbetweenness” through which Bhutan is understood and located on a map (“inbetween India and China”). I argue that this understanding naturalizes a contemporary geopolitics with little depth about how this inbetweenness has shifted over the centuries, thereby constructing a timeless, obscure, and remote Bhutan that is “naturally” oriented southward. I trace how the construction of Bhutan's asymmetrical inbetweenness is nested in the larger story of the formation and consolidation of imperial British India and its dissolution, and the emergence of post-colonial India as a successor state. I identify and analyze the key economic dynamics of three phases marked by commercial, production, and security interests, through which this asymmetrical inbetweenness was consolidated. Bringing together sources from different disciplines and archival work, this account also challenges some of the dominant historical scholarship on Bhutan in each phase. I conclude by emphasizing that critical work at the intersection of geographical/political/historical contingencies is important to the subalternizing of geopolitics, which recognizes the myriad ways in which dominant powers have shaped both the geopolitical environment as well as knowledge-making that has constrained small states.