In the last fifty years, abortion rights in the United States have gone from being criminalized in most states, to being legal on a federal level, to being regulated through individual state legislatures. In 1973, the landmark abortion case Roe v. Wade granted fecund persons a federal right to abortion for the first time in this nation’s history. To do so, the Supreme Court conceived of abortion rights within a rhetoric of expertise. The Court relied on legal, medical, and personal conceptions of expertise as knowledge, procedure, and deference to ground abortion rights in a precedent of privacy tied to the trimester framework. Since its codification, multiple cases at the Supreme Court and lower court levels have challenged the precedent established in Roe. These challenges have worked to both protect and constrict fecund persons’ abortion rights to various degrees. Each of these post-Roe cases have reconfigured the triangulation of expertise to make sense of abortion rights in their particular political and temporal moments. For instance, the landmark abortion case Planned Parenthood of Southeastern Pennsylvania v. Casey (1992) sought to reinforce the precedent in Roe by clarifying its legal and medical inconsistencies with the undue burden standard. Thirty years later, the Court in Dobbs v. Jackson Women’s Health Organization (2022) decided such inconsistencies warranted returning the abortion decision back to the states. The ability for abortion rights to undergo such a significant shift legally exposes the rhetorical paradox of expertise. The last fifty years of abortion law indicates the inability of legal and medical knowledge and procedures to consistency define the boundaries of legal abortion. But it also shows how the Court has deferred to these expert institutions time and time again to first expand, and then constrict, fecund persons’ personal expertise over the abortion decision. The Paradox of Expertise explores the complex triangulation of expertise in abortion law through an analysis of three pivotal U.S. Supreme Court cases: Roe (1973), Casey (1992), and Dobbs (2022). In each of these cases, the justices interpreted this triangulation in differential ways to shift the boundaries of legal abortion. In Chapter One, I explore how Roe read the legal-medical history of abortion to authorize the trimester framework and regulate fecund persons’ abortion rights and expertise. By regulating abortion through the trimester framework, the Court entangled legal, medical, and personal expertise in a complex web that ultimately privileged legal and medical expertise throughout a fecund person’s pregnancy. In Chapter Two, I analyze Casey to show how the Court responded to the ambiguities presented by the trimester framework. In Casey, the Court reinterpreted the precedent in Roe to affirm abortion rights under an undue burden standard. Because the Court failed to define this standard in a consistent manner, future courts continued to battle over the ambiguities of abortion law. In Chapter Three, I examine the decision in Dobbs to show how such legal battles over expertise allowed the Court to reinterpret abortion history and warrant returning the abortion issue back to the states. But because the Dobbs Court failed to clarify the past inconsistencies in abortion law, state legislators, medical physicians, and fecund persons struggle to make sense of the legal, medical, and personal barriers to abortion access in the present moment. Today, the current landscape of abortion politics is still mired in the paradox of expertise that foreshadows the long road ahead for pro-abortion advocates and those seeking abortion access and care.