Tsai Ing-Wen, Taiwan’s first female president, is one of the most prominent female leaders in the world. Having completed her two terms in office (2016–2024), her tenure provides a compelling basis for examining questions about her role within the context of female leadership in Asia. Is Tsai Ing-Wen an exceptional female leader in Asia? How does she compare to other female leaders in the region? Why is studying Tsai’s case important? To explore these questions, supported by the 2022 Taiwan Fellowship, I conducted 38 in-depth, semi-structured interviews in Taiwan. This article begins by presenting the theoretical framework surrounding female leadership in Asia. It then describes the typical pathways through which women in Asia have historically gained political power. The analysis then turns to Tsai Ing-Wen’s political career to address the central research questions.