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This paper traces the cultural origins of Winnicott's concern with creativity and play to the discovery (or rediscovery) of imagination amongst the Romantic poets after the disillusion of their youthful revolutionary hopes. It shows how the imaginative power to transform the world was discovered in the failure to transform it politically; it champions Wordsworth's poetic interest in the relationships sustained by mental imagery over Coleridge's more famous philosophical interest in the faculty of imagination; and it discusses the profound affinity between Wordsworth's understanding of poetry and Winnicott's understanding of play—an affinity which is partly a diffused influence, since the cultured world of Winnicott's youth retained the high Romantic evaluation of imaginative activity, and partly an effect of their common hostility to the post-Cartesian division of experience into the categories of subjective and objective. Such division ignores the 'potential space' between the two, the space of play and poetry, of image, metaphor and symbol—a space which our common language is ill-equipped to explore. My paper therefore emphasizes the importance of paradox to both Wordsworth and Winnicott: for in so far as they were free of universalist habits of thought, religious or psychoanalytical, paradox enabled them to subvert scientistic categories of thought and celebrate the poetry of the relational in our experience.