On a winter morning in 2022 Raphael Wong and Figo Chan walked into Hong Kong’s Stanley prison to meet Jimmy Lai, the media billionaire who had been arrested two years before and was awaiting trial charged with national security offences.

They had all been part of the turbulent protests that had rocked Hong Kong in 2019, when hundreds of thousands took to the streets demanding democracy and more freedom in the Chinese territory.

They would also often meet for dinner, sometimes lavish meals, gossiping and bantering over dim sum, pizza or claypot rice.

In prison, he “loved eating rice with pickled ginger,” Chan said. “No-one could have imagined Jimmy Lai would eat something like that!”

But neither had they imagined a reunion at a maximum security prison, the protests crushed, friends and fellow activists jailed, Hong Kong just as boisterous and yet, changed. And gone was the owner of the irreverent nickname “Fatty Lai”: he had lost considerable weight.

Decades apart – Lai in his 70s, Wong and Chan about 40 years younger – they had still dreamed of a different Hong Kong. Lai was a key figure in the protests, wielding his most influential asset, the hugely popular newspaper, Apple Daily, in the hope of shaping Hong Kong into a liberal democracy.

That proved risky under a contentious national security law imposed in 2020 by China’s Communist Party rulers in Beijing.

Lai always said he owed Hong Kong. Although he is a UK citizen, he refused to leave.

“I got everything I have because of this place,” he told the BBC hours before he was arrested in 2020. “This is my redemption,” he said, choking up.

He wanted the city to continue to have the freedom it had given him. That’s what drove his politics – fiercely critical of the Communist Party and avowedly supportive of Hong Kong’s pro-democracy movement. It cost him his own freedom.

Lai harboured “a rabid hatred” of the Chinese Communist Party and “an obsession to change the Party’s values to those of the Western world”, the High Court ruled on Monday as it delivered the verdict in his trial.

It said that Lai had hoped the party would be ousted – or, at the very least, that its leader Xi Jinping would be removed.

Lai was found guilty on all counts of charges he had always denied. The most serious one – colluding with foreign forces – carries a maximum sentence of life in prison.

“Never,” Lai had said to that charge when he testified, arguing that he had only advocated for what he believed were Hong Kong’s values: “rule of law, freedom, pursuit of democracy, freedom of speech, freedom of religion, freedom of assembly”.

Monday’s verdict was welcomed by Hong Kong’s chief executive John Lee, who said Lai had used his newspaper to “wantonly create social conflicts” and “glorify violence”. The law, he added, never allows anyone to harm the country “under the guise of human rights, democracy and freedom”.

Back in 2022, before Wong and Chan left the prison, Lai asked them to pray with him, to Wong’s surprise.

Lai’s Catholic faith had deepened in solitary confinement – an arrangement he had requested, according to authorities. He prayed six hours a day and he made drawings of Christ, which he sent in the mail to friends. “Even though he was suffering,” Wong said, “he didn’t complain nor was he afraid. He was at peace.”

Peace was not what Jimmy Lai had pursued for much of his life – not when he fled China as a 12-year-old, not while he worked his way up the gruelling factory chain, not even after he became a famous Hong Kong tycoon, and certainly not as his media empire took on Beijing.

For Lai, Hong Kong was everything that China was not – deeply capitalist, a land of opportunity and limitless wealth, and free. In the city, which was still a British colony when he arrived in 1959, he found success – and then a voice.

Apple Daily became one of the top-selling papers almost instantly after its debut in 1995. Modelled on USA Today, it revolutionised the aesthetics and layout of newspapers, and kicked off a cut-throat price war.

From a guide to hiring prostitutes in the “adult section” to investigative reports, to columns by economists and novelists, it was a “buffet” targeting “a full range of readers”, said Francis Lee, a journalism professor at the Chinese University of Hong Kong.

Former editors and employees spoke of Lai’s encouragement – “If you dared to do it, he would dare to let you do it” – and his temper. One said he often swore.

They describe him as unconventional, and as a visionary who wasn’t afraid to bet on experiments. “Even before the iPhone was launched, he kept saying mobile phones would be the future,” recalled one of the paper’s editors, adding that he was full of ideas. “It was as if he asked us to create a new website every day.”

It had been the same when he owned a clothing label. “He was not afraid of disrupting the industry, and he was not afraid of making enemies,” said Herbert Chow, a former marketing director at a rival brand.

That was both his making and undoing, Chow said: “Otherwise, there would have been no Apple Daily. Of course, he wouldn’t have ended up like this either.”

An early TV commercial for Apple Daily featured the then 48-year-old Lai biting the forbidden fruit while dozens of arrows took aim at him.

It became a self-fulfilling prophecy.

It was his first taste of chocolate that beckoned Lai to Hong Kong as a boy.

After carrying a passenger’s luggage at a railway station in China, Lai was given a tip, and a bar of chocolate. He took a bite. “I asked him where he’s from. He said Hong Kong. I said, ‘Hong Kong must be heaven’ because I had never tasted anything like that,” Lai said of the encounter in a 2007 documentary, The Call of the Entrepreneur.

Life in Mao Zedong’s China was punctuated by waves of oppressive campaigns – to industrialise China overnight, to weed out capitalist “class enemies”. The Lais, once a family of business people, were blacklisted. His father fled to Hong Kong, leaving them behind. His mother was sent to a labour camp.

Decades later, Lai wrote of how of he and his sisters would be dragged out of their homes to watch a crowd forcing their mother to kneel while she was shoved and taunted – cruel public shaming that soon became the norm. The first time, Lai wrote, was terrifying: “My tears flowed freely and wet my shirt. I dared not make a move. My body was burning with humiliation.”

Uncowed, his grandmother finished every story with the same message: “You have to become a businessman even if you only sell seasoned peanuts!”

And so, at the age of 12, he set off for Hong Kong, among millions who fled the mainland – and Mao’s devastating rule – over the years.

The day he arrived, on the bottom of a fishing boat, along with about 80 seasick travellers, he was hired by a mitten factory. He described the long working hours as a “very happy time, a time that I knew I had a future”. It was there that one of his co-workers helped him learn English. Years later, he would give interviews and even testify at court in fluent English.

By his early 20s, he was managing a textile factory and after making money on the stock market, he started his own, Comitex Knitters. He was 27.

Business often took Lai to New York, and on one of those trips, he was lent a book that came to define his worldview: The Road to Serfdom by Nobel Prize-winning economist Friedrich Hayek, a champion of free-market capitalism. “People’s spontaneous reaction” and “the exchange of information” have created the best in the world, was his takeaway. To him, that was Hong Kong’s strength.

The book spurred a voracious reading habit. He would read the same book multiple times, and read every book by authors he admired. “I want to turn the author’s thoughts into my backyard garden. I want to buy a garden, not cut flowers,” he said in a 2009 interview.

After a decade in manufacturing, he was “bored” and founded the clothing chain Giordano in 1981, which became a fast-fashion pioneer. It was so successful that Tadashi Yanai sought advice from Lai when his Japanese label Uniqlo opened shops.

Lai launched stores in China, which had begun to open up after Mao died. He was “excited”, China “was going to be changed, like a Western country”, he said in the 2007 documentary.

Then in 1989, Beijing crushed pro-democracy protests in Tiananmen Square: a rude awakening for Lai and Hong Kong, which was set to return to Chinese rule in 1997 under a recent agreement by China and the UK.

Giordano sold tees with photos of Tiananmen protest leaders and anti-Beijing slogans, and put up pro-democracy banners in stores across Hong Kong.

A million people marched in Hong Kong in solidarity with student protesters in Beijing. Until 2020, Hong Kong held the largest vigil that mourned the massacre.

Lai said later that he “didn’t feel anything about China” until then. He had always wanted to forget that part of his life but “all of a sudden, it was like my mother was calling in the darkness of the night”.

The following year Lai launched a magazine called Next, and in 1994 published an open letter to Li Peng, “the Butcher of Beijing” who played a key role in the Tiananmen massacre. He called him “the son of a turtle egg with zero intelligence”.

Beijing was furious. Between 1994 and 1996, Giordano’s flagship store in Beijing and 11 franchises in Shanghai closed. Lai sold his shares and stepped down as chairman.

“If I just go on making money, it doesn’t mean anything to me. But if I go into the media business, then I deliver information, which is choice, and choice is freedom,” Lai said in the 2007 documentary.

He soon became a “very active participant” in Hong Kong’s pro-democracy movement, meeting leaders to discuss strategy, said Lee Wing Tat, a former lawmaker from the Democratic Party.

He became an outspoken critic of the CCP, writing in 1994: “I entirely oppose the Communist Party because I hate everything that restrains personal liberties.” He also started to voice concerns about the looming handover of Hong Kong, from Britain to China, in 1997.

“After more than a century of colonial rule, Hong Kongers feel proud to return to the embrace of the motherland,” he wrote. “But should we love the motherland even if it doesn’t have freedom?”

During the handover, however, China’s then-leader Jiang Zemin promised that Hongkongers would govern Hong Kong and the city would have a high degree of autonomy for the next 50 years.

The 2014 Umbrella Movement sparked by Beijing’s refusal to allow completely free elections in Hong Kong became another turning point for Lai.

Protesters occupied the city’s main commercial districts for 79 days. Lai turned up from 9am to 5pm every day, undeterred after a man threw animal entrails at him. “When the police started firing tear gas, I was with Fatty,” the former lawmaker Lee recalled.

The movement ended when the court ordered protest sites to be cleared, but the government did not budge. Five years later, in 2019, Hong Kong erupted again, this time because of a controversial plan that would have allowed extradition to mainland China.

What began as peaceful marches became increasingly violent, turning the city into a battleground for six months. Black-clad protesters threw bricks and Molotov cocktails, stormed parliament and started fires; riot police fired tear gas, rubber bullets, water cannons and live rounds.

Lai was at the forefront of the protests and served 20 months for participating in four unauthorised assemblies. A protester told the BBC he was surprised to see Lai: “To me, he’s a busy businessman, but he showed up.”

Apple Daily provided blanket coverage or, as critics would argue, a sounding board for an anti-government movement.

Government adviser Ronny Tong said Lai was “instrumental” in the protests because Apple Daily carried a “totally false” slogan – anti-extradition to China – which “caught the imagination of people who wanted to cause havoc in Hong Kong”.

Whether Apple Daily played a seditious role, and how much control Lai exerted over its stance was at the centre of his 156-day national security trial.

Lai instructed the editorial team to “urge people to take to the streets”, according to Cheung Kim-hung, former chief executive of Apple Daily’s parent company Next Digital, and a defendant-turned-prosecution witness. After the National Security Law took effect, the newspaper was raided twice and eventually shut down in 2021.

During the height of the protests, Lai flew to the US where he met then Vice-President Mike Pence to discuss the situation in Hong Kong. A month before the National Security Law was imposed, Lai launched a controversial campaign, despite internal pushback, urging Apple Daily readers to send letters to then US President Donald Trump to “save Hong Kong”.

All of this, the court ruled, amounted to a public appeal for a foreign government to interfere in Hong Kong’s internal affairs.

“Nobody in their right mind should think that Hong Kong can undergo any kind of political reform without at least tacit acceptance from Beijing,” Tong said. The protests in 2014 and 2019 “are totally against common sense”.

Beijing says Hong Kong has now moved from “chaos to governance” and onto “greater prosperity” because of the national security law and a “patriot-only” parliament. But critics, including hundreds of thousands of Hongkongers who have since left, say dissent has been stifled, and the city’s freedoms severely curbed.

Lee, the lawmaker, is among them: “When I first came to the UK, I had nightmares. I felt very guilty. Why could we live in other places freely, while our good friends were jailed?”

Lai’s family has been calling for his release for years, citing concerns for his health because he is diabetic, but their calls have been rejected so far. The government and Lai’s Hong Kong legal team have said that his medical needs are being met.

Carmen Tsang, Lai’s daughter-in-law who lives in Hong Kong with her family, says her children miss grandpa – and the big family dinners he hosted every two weeks. His loud voice scared her daughter when she was younger, but “they loved going to grandpa’s place… They think he’s a funny guy”.

She is not sure today’s Hong Kong has a place for Lai.

“If there’s a speck of dust in your eye, you just get rid of it, right?”