Leadership in Energy and Environmental Design (LEED) is the most widely recognised green building assessment system in the United States but is increasingly criticised for only rewarding incremental solutions towards sustainability. With differing perceptions of how green building is best achieved, here we focus on how geographical context and reuse of existing buildings are rewarded. The conceptual framework for our analysis draws upon a light green/deep green dichotomy in sustainability and architectural design. While a light green perspective achieves reduced energy consumption and pollution through technology and green gadgetry, a deep green approach focuses on local geographic conditions to work with natural climate systems through design informed by vernacular architecture, as well as the benefits of adaptive reuse. This study uses a descriptive case study analysis of LEED credit points earned in six certified buildings in Denver and Boulder, Colorado. Our analysis confirms that LEED rewards more light green approaches. There is limited motivation in pursuing sustainability through deep green methods, as recognition of them in LEED is quite minimal. We conclude that the balance against rewarding deep green design limits more transformative paradigm-shifting advances in sustainability. Recommendations for improvements to LEED are given, as well as a discussion on emerging local governance in regulating green building. This paper contributes to the emerging body of literature focusing on green building as a mechanism of urban sustainability, and draws up the geographic perspectives of scale, place, and the political and economic linkages between humans and the environment in cities.