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The founder/owner of a successful multimillion-dollar service supplier in a manufacturing industry and his oldest son, the heir apparent, created a family and business crisis that brought to the forefront a transgenerational legacy of crippling paternalism. Observed was fierce sibling rivalry, competitiveness, and envy, while at the same time, there was also intense drive to achieve and a yearning to gain a sense of personal self-worth and empowerment, as well as autonomy, recognition, and the family acceptance. The problematic legacy of psychological disturbance exemplified in the family dynamics were dramatically lived out within the context of the family business. With many possible points of entry to address the complexity of this family business crisis, two innovative steps were taken. First, two psychoanalysts formed a partnership—a kind of psychoanalytic team—to create what Winnicott (1965, 1971) might have referred to as a “transitional space”—within which to work with the business owner, his family, and the leaders of his family business. Second, a psychoanalytic process of collateral and self-analytic inquiry is introduced as an analytically informing and helpful model when a psychoanalytic team or partnership approach to an organizational or family business consultation would appear warranted.