This chapter provides the dominant rationales that are said to underlie freedom of speech, and it evaluates how the autochthonous narrative in Singapore combines a neo-Confucianist ethos with a principled pragmatic orientation. It examines one of the horizontal effects of Article 14 as it applies to the law of defamation. The chapter argues that the justifications behind the Lange and Reynolds privileges are relevant to the Singapore experience, and that courts in Singapore ought to consider a broader qualified privilege applicable to citizens that takes into account the Reynolds factors in defamation suits involving political public figures. It questions whether the 'four walls' approach to constitutional interpretation is really tenable in the twenty-first century. The chapter concludes that exciting times lie ahead for freedom of speech jurisprudence in Singapore as the country enters a new phase of experimenting with a more consultative style of government and encouraging a more active citizenry.