The Office of Information and Regulatory Affairs (OIRA) is responsible for reviewing executive branch agencies’ draft proposed and final regulations, coordinating the federal government’s regulatory agenda, approving government collections of information from the public, and developing and overseeing the implementation of government-wide policies related to information policy, information quality, peer review, privacy, and statistical policy. While some of those functions are statutorily granted, others—notably those related to regulatory policy—derive from presidential executive orders. Since presidents can, and do, rescind their predecessors’ executive orders with ease, it is striking that these regulatory oversight functions, and the economics-based framework underlying them, have not changed significantly through six very different presidential transitions. This paper reflects on OIRA’s evolution over the almost 40 years since the Paperwork Reduction Act created it in 1980 to understand what has made it so durable. Part I begins with an examination of executive oversight of regulatory practice before the creation of OIRA. Part II looks at how presidents from Reagan through Trump have used OIRA to achieve their regulatory goals. Relying in part on the author’s experience, Part III explores the durability of OIRA’s procedures and guiding principles and briefly comments on proposals for changes to these practices. Part IV concludes.