This Article delves into the life and work of Judge [Florence] Allen to provide insight to the contributions and jurisprudence of the first woman judge. For history questions what difference putting a woman on the bench might have made. Part I explores Allen’s early influences on her intellectual development grounded in her progressive and politically active family, and her close network of female professional friends. Part II discusses her pivotal work with the women’s suffrage movement, working with the national organizations in New York and leading the legal and political efforts in Ohio. This proactive commitment to gender justice, however, would not survive her ascension to the bench. Once on the court, few cases raised issues of women’s rights, and in those that did, Allen offered only neutral support. Instead, her initial entrée to the judicial profession on the common pleas court focused on judicial management, legal process, and being tough on crime, while supportive of defendant’s rights. Part III traces these cases, highlighting her notoriety as a judge against mafia and corrupt lawyers and judges. Part IV then analyzes Allen’s jurisprudence from her decade on the state supreme court, following the wide variety of cases before her and tracking her developing reputation as a moderate, but politically inconsistent judge. Part V explores Allen’s decisions from her twenty-five years on the federal court of appeals, reconciling her reputation as a Roosevelt liberal with her moderate and bipartisan decisions. The final section of the Article then analyzes Allen’s judicial career, tracing her failed nominations to the U.S. Supreme Court and evaluating her limited legacy to the profession. Her once zealous advocacy of gender justice fizzled into simple polite encouragement of women in the legal profession. Overall, this story reveals the jurisprudence of the first woman judge, crafted carefully to reflect a moderate judge, fitting within the male-centric norms of the profession, and discarding any promise of women’s advocacy on the bench.