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Over the past few years, the United States Supreme Court has issued highly salient decisions striking down environmental policy (West Virginia v. EPA, 2022) and student loan forgiveness (Biden v. Nebraska, 2023), to name a few, under the “major questions doctrine.” The major questions doctrine is a decision-making rule that calls for the Court to reject government agency authority when the claim of authority is of “vast economic and political significance,” and when Congress has not clearly provided the agency with the authority in that particular issue area. These decisions, and others using the major questions doctrine, are at odds with the long-standing Chevron deference (Chevron v. Natural Resources Defense Council, 1984) which argued that the Court should defer to executive agencies when analyzing ambiguous language in separation of powers disputes. Chevron was part of a larger movement during the 1980s and 1990s that saw the Court expanding the authority of the executive branch at the expense of Congress. However, Chevron was always at odds with cases like INS v. Chadha (1983), Bowsher v. Synar (1986), and Clinton v. New York (1998) which took a more formalistic approach to separation of powers, arguing for strict adherence to the processes and procedures in the United States Constitution. Although the Court has not yet specifically addressed the question of overturning Chevron, during the current Supreme Court term the Justices have been explicitly asked to overturn Chevron in two cases, Loper Bright Enterprises v. Raimondo and Relentless, Inc. v. Department of Commerce. While the major questions doctrine decisions may be at odds with Chevron as legal commentators have noted, the formalistic approach to lawmaking in the United State system of separation of powers is a logical extension of those previous Court decisions that were also at odds with Chevron, like Chadha, Bowsher, and Clinton. But with the major questions doctrine, the conservative majority on the Court is now empowering Congress at the expense of the executive branch, an approach that is counter to the previous conservative coalitions on the Court in the 1980s and 1990s. In this paper, we will conduct a qualitative, descriptive case study to illustrate the path dependent forces of law that came from Chadha, Bowsher and Clinton, and the impact these cases had on the creation of the major questions doctrine, while also analyzing the conservative shift from executive to congressional authority in separation of powers disputes.