The article analyzes the novelistic representations of the Assassins, originally a nickname for the Islamic sect of Nizari Ismailis that gained an almost independent currency in Western popular culture. The analysis will be based on a the following selection of past and contemporary Western historical-fiction literature: Vladimir Bartol’s Alamut from 1938, translated into French in 1988 and into English in 2004; Judith Tarr’s Alamut from 1989; James Boschert’s Assassins of Alamut from 2010, the first book of his Talon trilogy; and, finally, Scott Oden’s Lion of Cairo from 2010. The scope of the article is to demonstrate a double-bind re-orientalization of the Assassins in this selection of novels that significantly changes their traditional representations: on one side, they reshape the Assassins in forerunners of modern Islamic fundamentalism and terrorism, while on the other side, the Assassin is gradually transformed from an orientalized villain into an occidentalized hero, thus enabling a self-othering of the Western subject and an identification, rather than disqualification, with this specific Arabo-Islamic Other. The article’s highlighting of this double-bind re-orientalization therefore challenges Orientalism’s binary dichotomy of Occident/Orient and its ideological implications through the concept of self-Orientalism as a self-othering process.