This chapter evaluates the question of the ‘complex’ in a range of scientific, political and psychoanalytic contexts, asking not only where lines of connection and demarcation occur among specific distributions of meaning, value, theory and practice; but also probing the psychoanalytic corpus, notably Freud’s writings on the notion of a ‘complex’, in order to reframe various implications of the idea that this term tends to resist its own utilisation as both an object and form of analysis. This section establishes connections between three sets of theoretical questions: the common practice of describing modernity and its wake in terms of a drive towards increasing complexity; the meaning and cultural legacy of phrases such as ‘military-industrial complex’ and sundry derivations in the political sphere; and the intricacies and ambiguities subtending the term ‘complex’ within psychoanalytic theory. As a concept that Freud both utilised and repudiated, the provocative power of the term ‘complex’ is linked to the way it thwarts various attempts at systemization (providing nonetheless an apparatus of sorts through which contemporary science, Slavoj Žižek, Noam Chomsky, Freud, Eisenhower, and post-war politics can be articulated to one another).