In this paper, I examine the figure of Ali Pasha of Yannina through the lens of Western travellers and dramatists. I argue that Ali Pasha’s powerful political, larger-than-life persona challenges the ways in which his Western audience has constantly tried to contain, organize and domesticate him. I also problematize Said’s notion of the representation of the Orient, as I suggest that Ali Pasha responds to popular depictions and representations of him through the manipulation and mimicry of his image. I bring attention to travel accounts and dramas such as William Davenport’s Historical Portraiture of leading events in the Life of Ali Pacha and Mordecai Noah’s The Grecian Captive, and read them as ‘cultural texts’ that ultimately reflect more the anxieties and fears of Romantic culture in the wave of Philhellenism than the Despotic figure portrayed by Ali. Moreover, I suggest that the questions of Orientalism in Ali Pasha are more a matter of mimicry, to borrow Homi Bhabha’s term. Ali stages himself as the West sees him, thereby exposing the superficiality and arbitrariness of the manner in which he is defined. When reading diplomatic and travel narratives of Ottoman Greece, I argue in this paper that we encounter two experiences of Ali Pasha and Greece – the diplomatic and the cultural – at odds with one another. On the one hand, European diplomatic knowledge of Greece was bound up with qualms about Ali’s political and economic strength, and his geographically strategic position: “he is a remorseless tyrant, guilty of the most horrible cruelties, very brave & so good a general, they call him the Mahometan Bonaparte” (Byron BLJ I 228). On the other hand, the cultural impulses of Philhellenism and Orientalism cast him as weak, depraved, pathetic and even inconsequential. Despite the fact that many travellers were hospitably entertained in the Pasha’s court, they nevertheless published wildly popular travel accounts, many of which provided sensational portrayals of the cruel and sensuous Ali, and tragic depictions of an enslaved and oppressed Greece. I suggest that European travellers who visited his lands were greatly invested in seeing him in the most alien terms possible. Ali had to be weak and inconsequential, and he had to be other, and only in seeing him as such could Europeans fully feel their imagined affinity with Greece; ultimately, mocking the Pasha became a form of support for the Philhellenic Wars and the Hellenic cause.