One of D. W. Winnicott’s seminal contributions to our understanding of personality development is the notion of transitional phenomena. This refers to a child’s capacity to create objects and space that are neither fully real nor fully imaginary. The creation of a transitional space is essential to the child’s ability to recreate sensations of parental comfort. Transitional phenomena are equally essential in the preschooler’s development of the capacity to play. This paper argues that the need for transitional phenomena is also constant throughout life, and that a primary place where it comes to reside for many of us is in our fanatical allegiance to sports teams. We claim that being a fan is a true transitional phenomenon: so safely real, just like our play in earlier years, that we can be far more intense and uninhibited than we can be in almost any other activity, thus satisfying our feelings of passionate expansion within a secure base that are at the core of our personality development from the very start.