Tyrannicide is a political act, which Ford describes as ‘a circle within a circle within a circle’ limited to striking down illegitimate, capricious or impious rulers and constitutes the ‘only respectable link between ethics and political violence’.1 It is parasitic in nature, being reliant on extant illegitimacy for its legitimacy. Its history is also subject to the history of tyranny and is nearly as old; as soon as archaic Greece came to regard tyranny as negative, tyrannicide became legitimate. This chapter also considers two other concepts: tyrannophobia and tyrannophilia. Tyrannophobia, as defined by Hobbes, is an under-identified but simmering presence in tyrannical discourse which impacts on the ability to diagnose tyranny’s presence. Tyrannophilia, as defined by Mark Lilla, describes the interrelationships between theoretical discourse and political support of tyranny. Much of this book focuses on those discussing tyranny, rather than tyrants and tyrannophilia, but this chapter locates the connections between them.