Illusion can be viewed as a creative engagement with the world, and as a central psychic motivation and capacity, rather than as a form of self-deception. Winnicott and other Middle Group writers have understood integrative, imaginative illusion as an essential part of healthy living and psychosocial development. As such, it emerges and presents itself in a variety of ways, in transaction with the realities that support or degrade it. In its absence, varied difficulties in living ensue. To elaborate and illustrate this conceptualization, Freud's notion that the oedipus complex is resolved is reconsidered as a creative misreading of Sophocles' Oedipus trilogy, one based on the plausible illusion of a civilizing psychosocial development that would serve as a protective bastion against his experience of the political chaos and violence of the first decades of twentieth-century European history. Finally, the place of illusion and disillusionment among those most disillusioned by the recent election of Donald Trump in the United States is considered in relation to the recent right-wing populist turn.