A systems methodology for identifying, characterizing, and evaluating engineering solutions and policies that prevent the formation of brownfields is presented. Brownfields exist in very large numbers and pose serious environmental and health risks in developed countries around the world. As industries abandon unprofitable sites and development spreads to other parts of the globe, potential brownfield creation abounds which will further exacerbate the problem. Preventing the creation of brownfields in the first place should be a priority. However, it will depend on the availability of options (technology) and the incentives to implement them (policy). A retrospective look at the City of Kitchener, Ontario, Canada, shows that a $10,000 investment in prevention could have avoided $100,000+ of cleanup cost on former gas station sites. Similarly, leaking underground fuel tanks could be prevented in South Sudan with double-walled tanks and appropriate procedures for less than 2% of the cost of cleaning up fuel leaks. Additional health-related economic and social costs associated with consumption of hydrocarbon contaminated groundwater could also be avoided. Actual implementation of pollution prevention requires a systems approach. Our research focuses on enhancing the relationship between engineering and policymaking through systems thinking and providing practical decision making support tools to guide development in a sustainable manner.