Following a call for nominations of judges who demonstrated legal wisdom in their decision-making and over 250 nominations being received, 11 judges who were nominated multiple times were interviewed about the ways thedevelopment of legal wisdom is supported and hindered within educational and professional systems. A grounded theory analysis was conducted. Findings emphasized that wisdom is promoted by avoiding exclusively adversarial learning models, engaging in training via lived experience in clinics, mentoring, and self- and cultural-reflection to develop contextualized thinking. Judges described challenges related to isolation, being in underresourced systems, and being in elected positions. This study sheds light upon how judges learn to consider multiple sets of values when forming wise decisions.