The home of Jimmy Lai, multimillionaire tycoon and political rebel, sits towards the top of a hill on a quiet street in the Kowloon district of Hong Kong. The leafy avenue dotted with detached, low-rise houses is an oasis of calm in a city better known as a jumble of skyscrapers and tightly packed streets. As my taxi pulls up, I expect to see police officers surveilling one of Hong Kong’s most famous dissidents. But the only sign of anything unusual is an elderly Nepali security guard playing Bollywood hits on his mobile phone.

Lai is one of Beijing’s staunchest enemies in the Chinese territory. For years, he has used his publications, including Apple Daily, a blend of celebrity tittle-tattle and hard-hitting news, to needle China and champion free speech. During the pro-democracy protests that engulfed the city last year, he was at the forefront of the fight against Beijing’s creeping control of Hong Kong.

He ushers me into a bright conservatory filled with art and orchids that looks on to a bucolic garden. Hong Kong has long been a refuge for the region’s business and political elite — a status it has maintained following the handover of the city from British to Chinese rule in 1997. But following the demonstrations, Beijing has intensified its efforts to bring the city to heel — and Lai, a rare Chinese businessman to openly defy the Communist party, is one of its most important targets.

On August 10 Lai was arrested on suspicion of “collaborating with foreign forces” under the national security law Beijing imposed on Hong Kong in the wake of the protests, a charge that he denies. Reporters filmed him being carted away in handcuffs from his house. Hours later, police marched him through his newsroom; his own journalists live-streamed the perp walk from inside their office.

This scene in a city that has long been a beacon of press freedom in Asia shocked many Hong Kongers — and that was probably the point. For Beijing, Lai’s arrest was a signal that no one who challenged its authority was beyond reach. It seems inevitable that he will be sent to prison, possibly in mainland China. He is now on bail.

Lai, a burly 73-year-old with a cherubic face, is scrupulously polite when discussing his time under arrest. “They treated me, maybe because of my age, quite politely,” he says. He is as matter-of-fact as if he were describing a visit to the dentist. “I asked if I could be allowed to have a bath. They allowed me but the door had to be kept open. They didn’t treat me nastily.”

Some things in Hong Kong still work differently from in mainland China, I think to myself — as Lai knows only too well.

For nearly two hours Lai enthusiastically explains his journey from child refugee to entrepreneur to political activist. His story is a quintessentially Hong Kong one. He was born in the southern Chinese province of Guangdong, to a rich family with interests in shipping. When the Communists took power soon after, that wealth made them a target and his family “disintegrated”. His father borrowed some money and fled to Hong Kong and the family lost contact with him.

Lai’s mother was forced to go to a labour camp and only allowed to return at weekends. His elder brothers were sent away to school. That left a six-year-old Lai, his twin sister and a nine-year-old sister to largely take care of themselves. “I had to bring money to buy some rice every day,” he says. He initially sold items at a sidewalk stall. Later, when he worked as a porter inside the railway station and earned decent tips, he got a taste of life in Hong Kong.

“One day, a guy — I was carrying his bag — was walking and biting on a bar of chocolate. He gave me a tip and then eventually he gave me the rest of the bar he was eating,” he says. Lai was mesmerised. “‘Hong Kong must be heaven,’” he thought, if anything that tasted this special existed there. “I said to my mother that I needed to go.”

One of Lai’s staff places our first dishes — two plates of har gau — on a sparsely set table covered by a white tablecloth. Lai stands up and drizzles truffle oil over the steamed shrimp dumplings before shaving slivers of fresh truffle on top. The combination is pungent and wonderful.

At the age of 12, Lai obtained a permit to go to Macau and was then smuggled on a fishing boat to Hong Kong. The day he arrived, Lai was sent to the garment factory where he would work and live. “Hong Kong to me was another world. It really was like heaven because I never felt that free,” he says.

Lai’s ascent was swift. He realised that the most successful people in Hong Kong spoke English. With some help from a factory accountant who had been an English teacher, Lai learnt English and within two years was promoted to work with the traders who sold the company’s clothes abroad. By the time he was 21, he was managing the factory.

If Hong Kong offered freedom and opportunity, it was the US that provided the intellectual foundation for his politics. In 1969, he was sent to New York to sell sweaters to department stores such as JCPenney and Montgomery Ward. He was entranced. “America was great, it’s the greatest country ever, even today,” he says, as he dishes out chunks of steamed grouper with spring onion and ginger, giving me a fin.

A retired Jewish salesman became his mentor. After Lai spent an evening “bad-mouthing communists”, a friend of the mentor gave him a copy of The Road to Serfdom by Friedrich Hayek. Lai’s English was still shaky, but he ploughed through it. “I was very touched reading Hayek, by his passion for freedom,” he says. “I’m a born entrepreneur but I wouldn’t have been advocating for freedom.” A bust of Hayek still sits in the reception of Lai’s media group HQ.

As his political fire was stirring, Lai bought a factory back in Hong Kong, using his bonus to speculate on the stock market to make enough to pay for it. He went on to launch Giordano, a high street fashion retail chain. The brand expanded worldwide, went public and made Lai a fortune.

But his political and commercial interests soon collided. During the Tiananmen Square protests in 1989, he sent T-shirts emblazoned with slogans backing the movement to the demonstrators. When, a few years later, Chinese premier Li Peng, the leader most closely linked to the bloody crackdown on the protests, justified the actions, Lai was incensed. He had already launched Next Magazine, his first media business, and wrote a column calling Li “a turtle’s egg”, a Chinese insult comparable to calling someone “a son of a bitch”. The Communist party told Giordano it had five days to sell Lai’s stake or its shops in mainland China would be shut.

Most entrepreneurs I know would be devastated to be forced out of their company. Lai says he wasn’t. “By the time this happened, I was already bored by the business,” he admits.

Lai hoped China would liberalise and launched Next and Apple Daily partly with that in mind. “You can deliver freedom through media,” he says of his thinking at the time. Next Digital, Lai’s media group, is listed in Hong Kong and Apple Daily, the city’s biggest pro-democracy newspaper, publishes salacious celebrity fodder and also pursues political campaigns; its front pages are often waved by protesters. “You can’t do [only] serious things and expect people to buy it,” Lai says of this use of sex and gossip to sell copies.

Lai now says he was overly optimistic. Central control has tightened under Xi Jinping, the country’s most dominant leader since Mao Zedong. Lai sees China’s relationship with the world as a clash of values. Until Beijing accepts the west’s, he argues, it will never be a reasonable actor. “The free world has only one set of institutions and those are western institutions that evolved from western civilisation,” he says.

We are speaking shortly before the US presidential election. Lai wanted Donald Trump to win. He is a particular admirer of Trump’s aggressive stance towards China. “He deals with reality, he’s not a gentleman. He plays hardball and this is effective,” Lai says. “The only way to avoid war with China is to threaten war,” he adds.

Lai thinks the anti-China attitude in Washington is now bipartisan, adding that Beijing’s handling of Covid-19, which started in Wuhan and spread worldwide after authorities initially downplayed the situation, has entrenched that view. But he worries that the Democrats’ antipathy to Trump could lead a Biden administration to soften or reverse some of his policies.

China sees Lai as a foreign stooge and decries what it calls foreign interference in an internal matter. The protests were the biggest open challenge on Chinese soil since Tiananmen, and Beijing wants Hong Kong to remain a global financial centre but under closer political control. Lai denies the accusation of being a western puppet. But shortly after our lunch, he was mired in controversy after it was revealed that Mark Simon, a close aide, had used Lai’s money to help compile a dossier about alleged business links of Hunter Biden, Joe Biden’s son, to the Chinese Communist party. The report was promoted by some Trump supporters. Lai denied any knowledge of the effort and Simon later resigned but the affair raised questions about Apple Daily’s ethics and probity.

Lai’s remarks and record reflect how Hong Kong has been caught in the middle of the US-China standoff. The Trump administration has said it no longer views the city as autonomous from Beijing and has sanctioned Hong Kong officials. Lai’s pro-Trump stance put him at odds with some other activists, who thought the president would ditch Hong Kong if it suited his purposes.


I ask if last year’s protests have simply accelerated the end of Hong Kong’s semi-autonomy. “Definitely,” he says, adding that if some protesters hadn’t resorted to violence, the national security law would not yet have been imposed. Even in the face of police brutality, he says, non-violence is the only way to maintain the moral high ground and would have been more astute tactically. Still, he adds, it was inevitable that Beijing would eventually take control.

Doesn’t this mean the protests were self-defeating? A movement that expedites the very thing it is fighting against hardly seems a desirable result. “At least we fought, we showed our dignity and that Hong Kong people aren’t just people who are money makers,” he replies. “We have a soul, we have dignity, we have pride as human beings. That’s important. We can’t have mass resistance again but we haven’t given up.”

One Hong Kong entrepreneur who backed the protests and was aghast at Lai’s arrest told me that the focus now should be negotiating a way to operate under the new conditions. Business is focused on the short term and making money, Lai says. But Beijing’s squeeze on the rule of law will force many to reconsider. “The problem of doing business without the protection of the rule of law will sink in when you get in trouble with a Chinese business partner.”

Since the handover, Hong Kong has remained Asia’s leading financial centre. But a cloud now hangs over commerce in the territory following the imposition of the national security law, with companies unclear how to enforce the rules. Local tycoons and executives at foreign companies have not spoken out for fear of angering Beijing. HSBC publicly backed the NSL, a move it said was about adhering to local laws, and was lambasted by British MPs and institutional investors. The NBA was also hit hard after the former boss of the Houston Rockets retweeted a message in support of the Hong Kong protests, prompting the cancellation of pre-season games in China and broadcasting deals.

A week after my lunch with Lai, the consequences of taking on Beijing were even more evident when Chinese regulators killed the $37bn initial public offering of Ant Group, the financial technology company founded by Jack Ma, just days before it was to be listed in Shanghai and Hong Kong. The decision is widely seen as political, after Ma, China’s best-known entrepreneur, criticised Beijing in a public speech last month. The Communist party pushed back against the challenge to its authority, even though it deprived Hong Kong of a high-profile listing. All of this makes Lai’s interventions exceptional.

Dessert has arrived: a plate of melon to share, warm crispy bao filled with custard, and a bowl of sweetened almond milk, into which Lai shaves more of the truffle. For now Lai insists that he is still focused on his business and continuing to speak out against China. Alongside its operations in Hong Kong, Apple Daily has a sister publication in Taiwan.

His more immediate concern however must be the threat of prison, even though he has lived with daily intimid­ation — he has been the subject of a murder plot and petrol bombs have been thrown at his house — for years. Lai, who holds British citizenship, is adamant that he has never considered quitting the business or the city that gave him his freedom. “A captain can’t jump ship. You may save your life but you will live in hell,” he says.

“I’m free!” he says. “Even when I’m facing jail time. I know I’m not guilty, I haven’t done anything wrong. There is no weight on my conscience.”

But now, for the first time in our conversation, he cracks. His Catholicism has girded him for any punishment but when I ask about his family, he chokes up; two of his sons were arrested on the same day as he was.

“The only thing I worry about is the family. If they use the family against me, I don’t know what I would do,” he says, wiping away tears. “That’s the only thing I worry about.” Lai succumbs to his emotions only fleetingly. “My life has been really good. Even if they nail me on the cross, that’s fine,” he says.

Lai is ready to get back to work and bids me farewell from his front porch. I grab a taxi and head back down the hill, into the heart of a city facing a future as uncertain as one of its biggest champions.