Globally, buildings contribute thirty percent of the CO2 emissions yielding 8.6 billion tons annually. A majority of existing buildings in the United States, and worldwide, will need to undergo a retrofit for environmental sustainability. The aim of the research is to investigate the process and the players involved in the retrofitting of buildings, and identify the enabling and hindering factors within the relationships of key stakeholders. This study will expand upon the green business case for stakeholders involved in the retrofit of existing buildings. Toward these goals, the study employs a case study methodology with qualitative research design in which surveys and interviews are conducted with key players of retrofit projects. Results will be compared to a theoretical basis of the LEED for Existing Building and Operational Maintenance program. Through thorough analysis, the study assesses commonalities and uniquenesses within the stakeholders of different cases. The research intends to establish reasoning about the slow rate of the sustainable industry, and suggests what must occur for the system to adapt accordingly to become more applicable and to accelerate the transformation of the existing building stock, given the complexities of the built environment sector.