Reflections on an Extraordinary Career: Thoughts about Gerald Caplan’s Retirement Abstract: The occasion for this essay is the retirement of my colleague Gerald Caplan. But this is not a sentimental account of a friend’s career. Instead, I take the opportunity of Jerry’s retirement to reflect on the role of a thoughtful principled conservative as a Washington insider and as an academic. The essay explores three areas of Jerry’s distinguished career: the first is a discussion of his role in saving the Legal Services Corporation when it was under attack from the right wing, within and without the Reagan Administration. The second topic focuses on Jerry’s widely cited and highly regarded critique of Miranda v. Arizona. I consider whether criminal defendants would have gotten greater protection from coercive police practices, had the Court followed his approach, rather than the approach it took in Miranda. The third section focuses on Jerry’s role in developing police regulations for the District of Columbia’s Metropolitan Police Department. Understanding the police from the perspective of an insider, Jerry disagreed with Mapp v. Ohio. Yet, because of a conservative’s belief in limiting governmental power and in good government, Jerry’s proposals offered the promise of limiting police abuse. Indeed, that section explores whether his approach would have yielded greater protection from abuse while preventing backlash against the criminal justice system.