This chapter examines the life and contributions of Singapore's Chief Justice Chan Sek Keong as a towering judge. Chan’s imprint on Singapore public law goes beyond his jurisprudential contributions and extends to fostering a mindset shift that has led to a reformed image of public law litigation as a professional and legitimate endeavour, and not simply a political and politicised activity. In presenting Chan as a towering judge, we conceptualise ‘towering’ as a relative and contextualised idea. Chan towers not only because he is one of the best legal minds in Singapore, and is more committed and diligent than most, but also because he was able to navigate what would be considered a limited policy space in a dominant-party state. Accordingly, although his jurisprudence may be described as minimalist in some quarters, we present his judicial minimalism not as judicial conservatism but as judicial courage.