In a tribute to Paul Ornstein, this article describes how Paul was one of the rising generations of self psychologists that embraced radical ideas that were opposed to the philosophical, theoretical, and therapeutic ideologies of the day. After highlighting his unfettered courage and optimism, I describe how Paul built on Kohut’s innovations, helping to spearhead a seismic shift in our philosophical and theoretical understanding of the underpinnings of psychoanalysis. I was fortunate to have the opportunity to discuss these major transitions with Paul during two years of taped Wednesday afternoon conversations. The article shares with you excerpts on selected issues from our conversations, covering topics such as how Paul found self psychology, empathy, the unconscious, the therapeutic alliance, curative fantasy, supervision, transmuting internalization, selfobject transference, and interpretation. It is through these exchanges that the breadth and depth of Paul’s clinical wisdom is most apparent.