Winnicott positioned his psychoanalytic style as distinct from Freudian and Kleinian theory, while his clinical practice was viewed by many as too enigmatic from which to establish a suitable theoretical framework. This article explores the role of boundaries within his practice and discusses whether he could be considered a “boundary artist” in the analyst's chair. Winnicott's underlying philosophy and clinical approaches are examined in relation to the analyst's intrapsychic boundaries and the permeable border between the roles of analyst and analysand—particularly with regard to his notion of transitional space. Despite Winnicott exhibiting narcissistic tendencies that may have blurred the boundaries of the therapeutic frame, this critique demonstrates how he used his unique skill set to ensure boundary crossings could benefit the therapeutic process whilst avoiding harmful violations. Additionally, we will also consider the more problematic implications of Winnicott's practice on modern relational psychotherapy.