Otto Will was one of the most creative psychotherapists of the twentieth century, yet his work is relatively unknown today. This paper strives to transmit his legacy. During his career at Chestnut Lodge and Austen Riggs, Will taught by example, inspiring others to engage in long-term, psychoanalytic treatment of psychosis. Deriving inspiration from his analysts, Harry Stack Sullivan and Frieda Fromm-Reichmann, he explored the healing power of human attachment and relatedness. As a therapist, he presented himself in all of his flawed humanity, admitting mistakes, and acknowledging limitations. Such human responsiveness engendered similarly human responses in the other. Through cultivating attachment and forging vital relationship with severely traumatized patients, he manifested a unique gift for connection. I draw upon my own experience as his student and colleague of twenty-three years to recount his personal and professional history and to examine his unique contributions to technique. Clinical examples and stories demonstrate Will’s singular “artistry of relationship.”