In a 1924 communiqué from the British High Commission in Constantinople to London, the author expressed concern about a Turkish newspaper article and accompanying illustration. He noted: “It is a significant fact that the Ileri of February 5th, 1924 published an attack on the Caliphal House of a kind more insidious and at the same time rather more gross than any which has hitherto come to my notice.” Indeed, the published piece in question caricatured the Ottoman caliph as a corpulent elderly gentleman indulging in carnal pleasures and other excesses while the common man endured heavy taxation. In response, the India Office expressed alarm over this type of visual rhetoric and its potential to rouse pro-caliphal segments of India’s Muslim population already voicing dissent through the Khilafat Movement. In this paper, I examine select Turkish and South Asian print media coverage, particularly satirical visual material, critical of Ottoman autocracy and of British political hegemony within the context of the failing Ottoman Empire, the emergent Turkish Republic, and the Indian struggle for independence. I explore the complexities and nuances the images (and texts) reveal about the Khilafat movement’s anti-colonial stance, its connections to other colonies still in the British Empire but aggressively pulling on the reins, its implications for the larger Muslim world as Turkey unmoored itself from the anchorage of political Islam, and British interventions to curb its growing appeal using heavy censorship.