Essential Aloneness presents a series of lectures on DW Winnicott delivered by Christopher Bollas in the 1980s to students and staff of the Institute of Child Neuropsychiatry at the University of Rome. Those attending were familiar with Winnicott’s works; indeed, many were expert. But a question remained. How do you use Winnicott’s concepts in the clinical space? Bollas not only addresses that question but also writes about his own clinical formulations at the time, such as ‘the transformational object’ or ‘the unthought known.’Each chapter contains a unique and distinct talk, as delivered and suffused with the aliveness that is a hallmark of in-person lectures, with Bollas exhibiting a remarkable flexibility of scope and focus in order to meet the attendant group’s clinical interests. The book teems with questions of Winnicottian psychoanalytic theory and practice no less relevant today than when the lectures were first delivered. These questions identify the subtle and complex positions taken by Winnicott, as understood by Bollas and other analysts in the United Kingdom and in Italy, who worked with him and knew how to make use of the Winnicott object. One of Winnicott’s literary editors, Bollas brings a unique perspective in real time to the challenges Winnicott’s thinking posed to the psychoanalytical, literary, and intellectual culture in the United Kingdom and abroad in the decade after Winnicott’s death.