In the early hours of 9 February 2026, a Hong Kong courtroom delivered a verdict that echoed far beyond its walls: Jimmy Lai, the 78-year-old media mogul and outspoken critic of Beijing, was sentenced to 20 years in prison. Convicted under the city’s sweeping national security law of conspiring to collude with foreign forces and sedition, Lai’s fate has become emblematic of the erosion of freedoms in the former British colony. To his supporters, he is a martyr for democracy; to his detractors, a traitor who courted foreign interference. As Lai, frail and diminished after more than five years in custody, nodded calmly at the sentence, the world watched a man whose rags-to-riches story mirrors the rise and fall of Hong Kong’s once-vibrant spirit of resistance.
Born Lai Chee-ying on 8 December 1947 in Guangzhou, southern China, Jimmy Lai’s early life was marked by poverty and upheaval. The son of a factory worker, he grew up amid the chaos of Mao Zedong’s communist revolution. At just 12 years old, in 1959, Lai stowed away on a boat to Hong Kong, then a British territory teeming with refugees fleeing the mainland. Arriving penniless, he began working in a glove factory, earning a pittance but harbouring ambitions that would propel him to unimaginable wealth. “I came to Hong Kong with nothing but a hunger for freedom,” Lai once reflected in an interview, a sentiment that would define his later activism.
Lai’s ascent in the business world was nothing short of meteoric. Starting as a lowly knitter, he quickly rose through the ranks, learning the intricacies of the garment trade. By the 1970s, he had saved enough to invest in the stock market, amassing a small fortune. In 1981, he founded Giordano, a casual clothing chain inspired by global brands like Gap and Benetton. Giordano expanded rapidly across Asia, turning Lai into a billionaire by the 1990s. His entrepreneurial flair was matched by a sharp eye for opportunity; he sold Giordano in 1989 amid fears of the impending handover of Hong Kong to China in 1997, pocketing millions. But Lai’s interests were evolving. The 1989 Tiananmen Square massacre, where Chinese troops crushed pro-democracy protests, profoundly affected him. “It was a wake-up call,” he later said. “I realised that without freedom, prosperity means nothing.”
This epiphany led Lai to pivot from fashion to media. In 1990, he launched Next Magazine, a tabloid known for its sensational exposés on celebrities and politicians. Five years later, in 1995, he founded Apple Daily, a newspaper that blended bold journalism with a pro-democracy slant. Apple Daily quickly became Hong Kong’s most popular Chinese-language paper, famed for its colourful graphics, investigative reporting, and unapologetic criticism of Beijing. Lai used his platform to champion human rights, often publishing articles that lambasted the Chinese Communist Party (CCP). His conversion to Catholicism in 1997, influenced by Cardinal Joseph Zen, a vocal critic of Beijing, further deepened his commitment to social justice. Lai’s media empire, under Next Digital, grew to include digital outlets and even ventures into Taiwan, solidifying his status as a thorn in the side of authoritarianism.
Lai’s activism intensified in the 2010s, as Hong Kong’s pro-democracy movement gained momentum. He was a key figure in the 2014 Umbrella Movement, where protesters occupied streets demanding universal suffrage. But it was the 2019 anti-extradition bill protests that thrust him into the global spotlight. Apple Daily provided extensive coverage, framing the demonstrations as a fight for Hong Kong’s soul against encroaching mainland control. Lai himself marched in rallies, donated millions to pro-democracy causes, and met with US officials, including then-Vice President Mike Pence and Secretary of State Mike Pompeo, to lobby for international support. These actions, prosecutors would later argue, amounted to collusion with foreign powers. Lai dismissed such claims, insisting he was merely advocating for universal values like freedom and the rule of law.
Beijing’s response was swift and severe. In June 2020, following the protests, China imposed a national security law on Hong Kong, criminalising secession, subversion, terrorism, and collusion with foreign forces. Lai was among the first high-profile targets. Arrested in August 2020 during a raid on Apple Daily’s offices, he was charged with fraud and later national security offences. By December, he was denied bail and imprisoned, marking the beginning of over five years in custody, much of it in solitary confinement at Stanley Prison. Apple Daily was forced to shut down in June 2021 after its assets were frozen and staff arrested, a move that silenced one of the last bastions of independent journalism in the city.
Lai’s trial, which began in December 2023 after multiple delays, was a protracted affair lasting 156 days. Prosecutors accused him of using Apple Daily to incite sedition and conspire with foreign entities to impose sanctions on China and Hong Kong officials. Key evidence included articles calling for international intervention and Lai’s meetings with US politicians. Lai pleaded not guilty, testifying that his newspaper simply ‘stood on the right side of history.’ Defence lawyers highlighted his age and health issues, diabetes, heart problems, and significant weight loss arguing for leniency. Yet, in December 2025, he was convicted on all counts. The 20-year sentence handed down this week is the harshest under the security law to date, effectively a life term for the octogenarian.
The international backlash has been fierce. Human Rights Watch condemned the sentence as ‘cruel and profoundly unjust,’ while the US State Department called it a ‘mockery of justice.’ Lai’s son, Sebastien, described it as ‘life-threatening,’ noting his father’s deteriorating health could mean he dies behind bars. Supporters, including exiled activists and Western lawmakers, have rallied for his release, viewing him as a prisoner of conscience. Beijing, however, portrays Lai as an instigator of ‘anti-China riots,’ with state media Xinhua hailing the verdict as a victory for stability.
Lai’s story is inextricably linked to Hong Kong’s own trajectory. From a haven for free enterprise and expression, the city has transformed under Beijing’s grip, with over 1,800 political prisoners now detained, a figure rivalling authoritarian regimes with far larger populations. Lai, once dubbed ‘Fatty Lai’ for his rotund figure and love of food, now appears gaunt in court sketches, a shadow of the charismatic tycoon who built empires from scratch. His British citizenship has offered little protection; appeals for his release have fallen on deaf ears.
Yet, even in defeat, Lai’s legacy endures. He inspired a generation of Hongkongers to fight for autonomy, and his imprisonment underscores the high cost of dissent in an increasingly repressive China. As one former Apple Daily colleague told me anonymously, ‘Jimmy didn’t just report the news; he became it.’ Whether history will judge him as a hero or a provocateur, one thing is certain: Jimmy Lai’s unyielding pursuit of freedom has left an indelible mark on the struggle for democracy in Asia.
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