Jimmy Lai believed in “delivering freedom through media”. His Apple Daily newspaper was a staunch champion of Hong Kong’s democracy movement, and Lai was considered one of the Chinese Communist party’s most outspoken critics.

Now the rags-to-riches media mogul, who was among Hong Kong’s best-known and most colourful billionaires, has lost not only his media empire but also his personal freedom.

Having already spent almost three years in prison, the 76-year-old faces the prospect of spending the rest of his life there. In a landmark trial, which begins on Monday, Lai is accused of collusion with foreign forces and conspiring to publish seditious material. If he is found guilty as expected, he faces a maximum penalty of life in prison. Lai, who has British citizenship, is the highest-profile casualty of Beijing’s crackdown on the city and a sweeping national security law.

“Jimmy Lai is probably number one on Beijing’s enemies list,” said Thomas Kellogg, executive director of Georgetown University’s Center for Asian Law. “The clear goal here is for Lai to be sentenced to prison for the rest of his life.”

Jimmy Lai walks through the Stanley prison in Hong Kong in July
Jimmy Lai walks through the Stanley prison in Hong Kong in July © Louise Delmotte/AP

Lai is being tried under the National Security Law, introduced in 2020 in the wake of citywide pro-democracy protests. Many opposition activists have been jailed or fled, and independent media outlets have shut down.

In late 2021 Lai was sentenced to 13 months in jail after being convicted for inciting others to take part in a banned 2020 Tiananmen Square massacre commemoration. Last year he was sentenced to five years and nine months in prison on separate fraud charges, convicted for violating the terms of a lease contract for the headquarters of Apple Daily.

“He has given up everything he has for the idea of democracy,” Lai’s son Sebastien, now based in Taipei, told the Financial Times.

In some ways, Lai’s life follows the typical trajectory of Hong Kong’s self-made billionaires. Born in Guangdong province, Lai left his family and went to Hong Kong in 1960 after the Communist party took power in mainland China. He worked at a factory from the age of 12 and rose to manager in a decade.

By his 30s, Lai had founded his own fashion retail chain, Giordano, which expanded into the rest of Asia. Beijing expressed dissatisfaction with his strong stance against the bloody crackdown on protests in Tiananmen Square in 1989 and threatened to shut its stores in the mainland. He later sold his stake in the company.

His first forays into media came when he founded Next Magazine and its parent company Next Media in 1990. He set up Apple Daily in 1995. Both publications featured a mix of political advocacy and tabloid-style reporting of sex and gossip. Both were highly critical of the Chinese Communist party.

Apple Daily — whose daily circulation rose to as much as 500,000 after Hong Kong’s handover from the UK to China in 1997 — later played a pivotal role in mobilising people to participate in mass demonstrations in Hong Kong.

“You can deliver freedom through media,” Lai told the FT in an interview in 2020, as he explained his logic for setting up Next and Apple Daily.

From right: Jimmy Lai, Martin Lee, Szeto Wah and Joseph Zen
Jimmy Lai, right, participates in a march calling for universal suffrage during the 10th anniversary of Hong Kong’s handover to Chinese rule in 2007 © Ricky Chung/South China Morning Post/Getty Images

He also donated to pro-democracy parties and was close to prominent opposition figures including Martin Lee, founder of the city’s Democratic party. During the height of pro-democracy protests in 2019, he flew to Washington and met then US vice-president Mike Pence and secretary of state Mike Pompeo to discuss the situation in Hong Kong.

In August 2020 authorities moved quickly to disband his empire. Just weeks after the introduction of the National Security Law, Lai was arrested and led away in handcuffs as Apple Daily’s building was raided by about 200 police officers.

Apple Daily was subsequently shut down in mid-2021 after authorities froze its assets, raided its newsroom again and arrested some of its senior journalists on collusion charges. Hong Kong-listed Next Digital, formerly Next Media, became defunct later that year.

Lai’s high-profile arrest was “emblematic of a much wider campaign against press freedom in Hong Kong”, said Fiona O’Brien, UK director of Reporters Without Borders. “His case is being used as a deterrent to all independent voices in the media and civil society.”

The Apple Daily newsroom in May 2021
The Apple Daily newsroom in May 2021, one month before it was shut down © Peter Parks/AFP/Getty Images

In June this year the European parliament passed a resolution calling for Lai’s immediate release after a group of United Nations experts expressed “grave concerns” over his detention. His son, along with some human rights groups, have been pushing the UK government to pressure Beijing to release his father.

It was “disappointing and heartbreaking” that the UK government had not formally called for his father’s release, Sebastien Lai said. This week he met foreign secretary David Cameron to discuss his father’s case. Last month 10 Catholic bishops signed a petition demanding the release of Lai, a devout Catholic.

A UK Foreign, Commonwealth and Development Office spokesperson said Lai’s case “is a priority” for the government and had “been raised on multiple occasions with the Chinese Government”.

The Hong Kong government blocked Lai’s defence lawyer, UK barrister Tim Owen, from representing him last year, arguing foreign lawyers could pose a threat to national security.

Ahead of the trial, Beijing’s foreign ministry called Lai an agent who “took pride in foreign interference” and “pawn of the anti-China forces” whose crime of collusion with foreign forces “is clear”. In response to calls to release Lai, Hong Kong officials have said all lawbreakers must be “held accountable”.

Lai remains in “good spirits”, said a person close to him, even as he is held in solitary confinement at a maximum-security facility.

“My dad decided to essentially sacrifice everything that he has in order to stand up for these beliefs,” Sebastien Lai said. “He knew full well he could very well end up in prison, but he decided to stay with his people because he knew that that was the right thing to do.”

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