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Perhaps it is their role in our survival, or our economic growth, or the environment. Whatever the reason, energy and natural resource conflicts seems to be unique in the way they can drive significant doctrinal change even outside of energy and natural resource law. Pennsylvania has been a fountainhead of these conflicts. In 1921, Pennsylvania’s Kohler Act and lesser known Fowler Act, which sought to protect surface owners from anthracite coal mine subsidence and to increase tax revenue from anthracite mining, ignited the legal wrangling that eventually led to Pennsylvania Coal Co. v. Mahon. That U.S. Supreme Court decision transformed the Takings Clause of the Fifth Amendment and forever changed property regulation. In 2012, a series of acts of the Pennsylvania General Assembly seeking to capitalize on the hydraulic fracturing boom triggered a fiscal fight that resulted in the Pennsylvania Supreme Court’s 2017 decision in Pennsylvania Env. Def. Foundation v. Commonwealth, which gave self-enforcing legal meaning to the Environmental Rights Amendment of the Pennsylvania Constitution. This latter decisions both shifted Pennsylvania’s administrative and legislative law landscapes and may provide a more meaningful legal framework for constitutional environmental protection than currently exists in the United States. This paper compares and contrasts these two cases, which have so much and so little in common. The paper highlights a series of similarities and offers lessons about doctrinal change, environmental law, and advocacy strategy. In particular, this paper will focus on the way that case outcomes and legal reasoning can conflict. Penn Coal is a triumph of economic liberalism and a boon to the conservative property rights movement. Nevertheless, and has been noted elsewhere, it is an example of Justice Holmes’ famous progressive jurisprudence. Conversely, Pennsylvania Env. Def. Foundation is an unparalleled win for environmental protection, but it evidences a classically conservative approach to legal reasoning. The paper will conclude with an attempt to understand what we mean by the terms conservative, moderate, and progressive in the context of environmental law.