This chapter examines Jack Spicer’s 1955 play Troilus in the context of its relationship to Shakespeare’s Troilus and Cressida. While situating the play in relation to Spicer’s work more broadly, the chapter also looks at how Spicer rewrites and revisits crucial scenes and concerns from Shakespeare’s play. Pivotal here is the question of “emulation” in all its guises: admiration, jealousy, and imitation. Indeed, “emulation” as figure can be seen not only to govern much of Shakespeare’s Troilus and Cressida but the entire scene of Spicer’s project too, which is to a large degree an “imitation” of Shakespeare’s precedent and which in many respects follows the problematics of “emulation” as Shakespeare himself established them. This entire dynamic, of course, implies psychoanalytic theories of identification, narcissism, and projection, through which relations of both rivalry and erotic attachment, and the unstable border between these two, are negotiated. If Shakespeare’s Cressida, as the play insists, becomes a byword for erotic betrayal, Spicer’s revision teases out a paradoxical notion of fidelity, and a different vision of the ethics of responsibility in love.