This article illustrates the transtheoretical evolution of caring science within complex systems from the discovery of the theory of bureaucratic caring, in 1981, to the emergence of the metatheory relational caring complexity in 2011. The theory of bureaucratic caring, derived from research, is the sentinel grounded theory in the area of caring and economics, and complex healthcare systems in general. Its tenets remain applicable to contemporary nursing practice. Other grounded theories advanced from the original theory, including struggling to find a balance, the paradox between caring and economics, relational complexity, and relational self-organization in workforce redevelopment, as well as professional and patient relational caring questionnaires are presented and discussed.