This chapter uncovers the groundbreaking career of Mary MamYassin Sey, a Gambian judge who broke through the “glass ceiling.” She was the first Gambian High Court judge, Supreme Court judge, and the first African—and sole woman—on Vanuatu’s Supreme Court. Through elite legal interview and legal storytelling, the chapter presents Sey’s journey as a legal pioneer who, over the years, earned a reputation for her independence and relentless pursuit of justice, including handling high-profile corruption cases. Her story sheds light on critical issues within the legal sphere, including women’s representation, judicial independence, the role and impact of foreign judges, and the importance of community engagement. This chapter serves as a testament to the importance of Judge Sey’s work, aiming to document her exceptional path within both the Gambian and international judiciaries, and contributes to emerging literature on African women judges’ paths to leadership and the complexities of navigating power dynamics on and off the bench.