"President by Night" is the infamous nickname Park Chung Hee once gave to Pang Il-yŏng, the head of Chosun ilbo, South Korea’s largest daily newspaper. The nickname reveals the symbiotic nature of the relationship between the press and political regimes in authoritarian South Korea, which continued well past the transition to procedural democracy in 1987. Transforming itself from a watchdog to a lapdog to an attack dog, mainstream news media has continued to serve as a powerful stakeholder in the maintenance of conservative political regimes and agendas in twenty-first-century South Korea. Against this backdrop, the rise of new media as news media in the “post-broadcast” age, which took off with the internet, exploded with the podcast, and achieved dominance with YouTube, has been led by an irreverent and iconoclastic maverick named Kim Ou-joon. Tracing Kim's career over three decades from the founding of an internet newspaper to the launch of the wildly popular political podcast Nakkomsu, and to the recent establishment of a YouTube news channel that reached a million subscribers in the first three days of its livecast, this talk will map Kim’s sustained search for what he has termed an “alternate messaging system” onto­ the political and media terrains of his times to interrogate the relationship between media and democracy in twenty-first century South Korea.