Churchman dedicated his career to sensitizing systems scientists and other inquirers to the existence of what he referred to as "enormous problems." In his view these are problems that cannot be addressed by a single discipline or a single inquirer but by interdisciplinary teams of inquirers. This chapter tells the story of how a group of researchers, in the context of the Club of Rome (CoR) Prospectus on The Predicament of Humankind, proposed in the early 70s a very forward looking and innovative systems approach. It took over twenty years of research and development for the emergence of a paradigm of Structured Design Science (SDS) that has been tested in the arena of practice for the last fifteen years.The CoR prospectus introduced the concept of the Problematique as the "enormous problem" of the 20^th Century. In 1993, twenty-three years after the conceptualization of the Problematique, a small team composed of three of the original architects of the CoR proposal employed the SDS paradigm to conduct a retrospective inquiry of the global Problematique. The findings from this inquiry demonstrate that no significant progress had been made in terms of resolving the root causes of the Problematique in the ensuing twenty-thee years, i.e., 1970–1993. It is conjectured that a similar inquiry conducted today, i.e., ten years later, will reaffirm the lack of progress in resolving this enormous problem of huhumankind. The implications of these findings are significant for all systems scientists, and especially for students of Churchman's work.