In this paper, I interrogate the exhaustive ‘inbetweenness’ through which Bhutan is understood and located on a map (‘inbetween India and China’), arguing that this naturalizes a contemporary geopolitics with little depth about how this inbetweenness shifted historically over the previous centuries, thereby constructing a timeless, obscure, remote Bhutan which is ‘naturally’ oriented southwards. I provide an account of how Bhutan’s asymmetrical inbetweenness construction 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 specific phases (late 18th to mid 19th centuries, mid 19th to early 20th centuries, early 20th century onwards) marked by commercial, production, and security interests, through which this asymmetrical inbetweenness was consolidated. Bringing together sources from different disciplines combined with archival work, this account also challenges some 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.