Jimmy Lai once believed Hong Kong’s freedoms were worth any personal risk. That conviction ultimately led him from boardrooms and newsrooms to a maximum-security prison.
On a cold morning in 2022, veteran activists Raphael Wong and Figo Chan entered Stanley Prison in Hong Kong to visit Lai, the media tycoon arrested two years earlier under the territory’s national security law. The three men had been prominent figures during the mass pro-democracy protests of 2019, when huge crowds filled the streets demanding greater political rights and civil liberties.
Their friendship had once revolved around long dinners and animated conversations over shared meals. Prison life, however, revealed a very different reality. Lai, now noticeably thinner, had adapted to austere routines. Chan recalled being struck by how the billionaire, once known for indulgence, now enjoyed simple food like rice with pickled ginger.
The meeting underscored how profoundly Hong Kong had changed. The protest movement had been dismantled, many activists imprisoned, and the city’s political atmosphere transformed. Lai, in his seventies, remained a symbol of defiance for a generation that had hoped for a more open future.
As the founder of the popular Apple Daily newspaper, Lai used his media influence to openly challenge Beijing and support Hong Kong’s democratic movement. That stance became perilous after China imposed a sweeping national security law in 2020, criminalising acts deemed to threaten state power.
Despite holding British citizenship, Lai refused to leave the city. Shortly before his arrest in 2020, he told the BBC that he owed his success to Hong Kong and felt a moral duty to defend its freedoms. That decision would ultimately cost him his liberty.
This week, Hong Kong’s High Court delivered its verdict, finding Lai guilty on all charges, including collusion with foreign forces — an offence that can carry a life sentence. The court described him as fiercely hostile to China’s Communist Party and intent on reshaping Hong Kong’s political direction.
Lai has consistently rejected the accusations, insisting he merely advocated core values such as the rule of law, freedom of expression and democratic participation. Hong Kong’s chief executive John Lee welcomed the ruling, arguing that Lai had used his newspaper to inflame social divisions and that national security laws could not be undermined in the name of freedom.
During his detention, Lai’s personal life also changed. According to friends, he requested solitary confinement and turned increasingly to his Catholic faith. He spent hours each day praying and drawing religious images, which he sent to supporters. Wong recalled that, despite his isolation and uncertainty, Lai showed little fear or bitterness, appearing calm and resolute.
Jimmy Lai’s journey from billionaire publisher to convicted prisoner has come to symbolise the narrowing space for dissent in Hong Kong — and the personal cost of challenging China’s political red lines.
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