Ralph Greenson's The Technique and Practice of Psychoanalysis acted as a bible for generations of analysts on what to do and what not to do in psychoanalysis. Yet Greenson ignored the strictures of his own textbook, The Technique and Practice of Psychoanalysis, in his treatment of a number of superrich patients and celebrities, such as Marilyn Monroe and Lita Annenberg Hazen. This article presents new evidence from the examination of the papers of Ralph Greenson and Anna Freud at UCLA and the Library of Congress. Although it is well known that Greenson stretched boundaries with Monroe, his practice of blurring boundaries with other patients, and helping to funnel their money to Anna Freud's Hampstead Center, is not known. Hazen was not only President of Greenson's Foundation for Research in Psychoanalysis but was also, through Greenson's encouragement, a major contributor to Anna Freud's Hampstead Center. Greenson even went so far as to answer a personal advertisement on her behalf and fly to New York for a weekend to interview the suitor. These activities took place with Anna Freud's knowledge, approval, and collusion. Other cases are also discussed. If only he had taken his own advice.