This contribution explores the changing valences of the terms “Commonwealth” and “empire” through the lens of South Asian studies. I first investigate how the idea of the Commonwealth as a political genre for association and comparison was described by Sri Lankan, Pakistani, and Indian leaders. Taking foreign policy rhetoric as literary texts, I show how such political speech reveals competing and ambivalent meanings for the term in the region. I then draw on my experience as a co-editor of the journal South Asia: Journal of South Asian Studies to assess how the keywords “Commonwealth” and “empire” have been used in the pages of this journal. Through a mixture of large data patterns and close textual readings, I track when, where, how, and why these terms have mattered. I suggest that the turn captured by the renamed Literature, Critique, and Empire Today resonates with the organic ways that South Asian studies conceptualizes broader paradigms of transnational power and inequality that have shaped, and continue to inform, the region.