Jimmy Lai, the founder of the now-closed Apple Daily newspaper in Hong Kong, has been handed a 20-year prison sentence for violating the controversial National Security Law, which targets anti-government activities. This severe penalty has shocked many, including former colleagues who regard it as 'equivalent to the death penalty', underscoring the dire implications of dissent in today's Hong Kong. Former executive Lee Ka-chung expressed disbelief over the harshness of the ruling, stating that the media's role as the 'fourth estate' should involve criticizing the government, a function that seems to have been criminalized under recent laws. Lee, who worked alongside Lai from 2009 until the newspaper's closure in 2021, highlighted Lai's fearless approach to journalism, believing that there should be no taboos in reporting. Lai consistently emphasized the importance of free expression and stood firmly against the Communist Party's regime. During the implementation of the National Security Law, when many media outlets were retreating from critical reporting, Lai supported the creation of programs that promoted accountability, demonstrating his commitment to a free press. As Hong Kong navigates a complex political landscape post-national security law, the judgment against Lai not only intensifies the scrutiny on media freedoms but also signals a chilling precedent for journalists and the public at large. The measure of such sentences raises questions about the future of dissent and democratic values in a city that was once known for its vibrancy and freedom of expression, thus framing these events as a significant moment in the struggle for media rights in Hong Kong.