It was not the first time in his long and eventful career that media mogul Jimmy Lai became the story, and it wouldn’t be the last. But it was certainly the most dramatic. On 10 August 2020, about 200 police officers frogmarched 72-year-old Lai out of the offices of his embattled newspaper, Apple Daily, as they conducted a raid on the publication, which had vigorously supported Hong Kong’s pro-democracy protests. More than 10,000 people tuned in to watch as the newspaper’s reporters defied police warnings and streamed the scene live on Facebook. As if to underline the extent to which the authorities now controlled the story, Lai had actually been arrested at his home earlier that morning. He had been brought to the offices to oversee one of the final blows to the newspaper that he had founded 25 years earlier. It was intended as a final humiliation for the outspoken tycoon who had spent his adult life opposing the Chinese Communist party (CCP) and its increasing grip on Hong Kong. The next day the paper’s front page showed a picture of Lai in handcuffs, with the headline “Apple Daily must fight on”. It was forced to close just under one year later, after its assets were frozen. Lai was charged with violating Hong Kong’s new national security law by colluding with foreign forces. He has since been charged with fraud, sedition and organising and participating in an unlawful assembly. He has been convicted on several of those counts and is awaiting his trial for the most serious national security charges. Once one of Hong Kong’s richest and most outspoken pro-democracy activists, Lai is now in solitary confinement in a maximum-security prison. On 26 September, he marked his thousandth day in prison. But still, he says, life is “full and at peace”. “There is always a price to pay when you put truth, justice and goodness ahead of your own comfort,” he wrote to a friend in 2021. “Luckily God has made this price a grace in disguise. I am so grateful.” Lai’s imprisonment has been condemned by international observers and human rights groups. His case is not just about the crackdown on free speech in Hong Kong. It is also the story of how the city’s once unique, uproarious spirit was quieted in the shadow of Xi Jinping’s China, which brooks no dissent, even at the cost of political and economic pain. Lai’s rags-to-riches journey “wasn’t the story of a lot of people”, says Kris Cheng, a journalist who left the city during the crackdown on the pro-democracy movement. “But it was the kind of story that resonated with a lot of people in Hong Kong … people look up to him, regardless of politics.” Jimmy Lai has always felt lucky. Born in one of the most tumultuous periods of Chinese history, he was just 10 years old when in 1958 Mao Zedong launched the Great Leap Forward, an agricultural collectivisation policy that resulted in the worst famine in human history. His father had fled the country, warning his only son never to go into politics. Tens of millions of people died. But Lai survived. At the age of 12, he snuck into the hold of a fishing boat and smuggled himself from mainland China into Hong Kong, a place that he had imagined as “heaven” after a traveller from the British colony had given him a chocolate bar a few years earlier. “The moment you feel freedom, it’s a high I never had again,” he said of his first moments in the city. He soon found work on the floor of a garment factory, eventually becoming a manager. As Hong Kong’s economy boomed, so did Lai’s fortune, which grew to new heights through the success of his own hugely popular clothing brand, Giordano. In the 1990s he pivoted to newspapers; his company, Next Digital, became the largest listed media company in Hong Kong. By 2008, he was worth an estimated $1.2bn, according to Forbes. Friends of Lai paint a picture of him that is equal parts zealot and genius. “He’s a really curious kind of renaissance man,” says Ron Gluckman, an American journalist who has known Lai since profiling him in 1999. After making his fortune in retail, Lai turned his attentions to media in the wake of the Tiananmen Square massacre, determined to help defend democracy through the dissemination of information. He also saw a business opportunity, as he had been forced to sell his stake in Giordano. Beijing had shut down his stores on the mainland in retaliation for insulting Li Peng, China’s premier, as “the son of a turtle’s egg with zero IQ”. Lai made a reported $280m from the sale, and strode into a media market that was hungry for gossip while full of foreboding about what the forthcoming handover of Hong Kong from British to Chinese rule would do to the city’s identity. Having already angered Beijing more than once, Lai knew what the handover might do to his fortunes as well. But he was “willing to be martyred for the cause”, says Gluckman. “And he believed 100% that it was worthwhile.” By all accounts Lai is fiercely intelligent, and wears it lightly. He taught himself English as a child labourer; the first book he finished, he reread 11 times to perfect his understanding. He is a voracious reader of volumes on economics, philosophy, business and, since his conversion to Catholicism, religion. Powerful men who lack a formal education sometimes worry about their intellectual credentials. Such insecurity seems never to have plagued Lai, who is as happy to play the buffoon as he is to inhabit the role of freedom fighter. He readily admitted that he copied the name for his clothing brand, Giordano, from a pizza joint in New York that he wandered into after feeling “munchy” having unwittingly eaten marijuana cookies. For someone who has invested considerable energy – and money – into accruing huge wealth, Lai has been relaxed about letting it go. “Being rich, you can be very poor,” he once said. “Because if you only have money, you lose meaning, you lose dignity, you lose everything as a human being.” He was referring to his commitment to activism, but it is also an approach he has taken in business. Lai’s passion is for starting companies rather than running them. “He always felt that he was more creative than he was operational,” says his son, Sebastien Lai. Simon Lee, a former employee, puts it more bluntly: working for a Lai company, “the failure rate was phenomenal”. In one instance, he lost $140m in six months in a failed attempt to launch an online grocery store. This rambunctious attitude was exemplified in the pages of Apple Daily, Lai’s newspaper, described by one academic as “a strange hybrid of frivolity and seriousness”. The newspaper launched in 1995 and had an agenda-setting reign until it was forced to close in 2021 after Beijing’s crackdown on freedoms in Hong Kong. Lai always knew that political winds might overpower market forces, and so he invested HKD$700m at the launch, enough to sustain losses until after 1997 if advertisers pulled out for political reasons (which many later did). Apple Daily was an instant hit. Within two months it was the second-biggest newspaper in the city. Its wild, colourful journalism was a “cultural shock to the whole journalism industry”, says Grace Leung, a retired media professor who wrote a book about the paper. Lai brought a racy, freewheeling sensibility to the staid publishing world. He knew how to “sell the sizzle”, recalls Mark Clifford, a former director at Next Digital. For several years, Apple Daily ran a pornography section, with reviews and pictures of brothels and sex workers. The newspaper was repeatedly fined for breaching Hong Kong’s obscenity ordinances, and on a separate occasion one of its reporters was jailed for bribing police officers, but Lai would treat such hiccups as “part of the production costs”, says Leung. In 2003, Apple Daily had the opportunity to throw its now huge influence behind Lai’s political views for the first time. Lai and his newspaper strongly opposed an attempt by the Hong Kong government to implement a piece of legislation known as Article 23, which would prohibit treason or sedition against Beijing. Apple Daily campaigned vigorously against the legislation, helping to turn out half a million people for a march on 1 July. The demonstration was a success, in that Article 23 was shelved. But it also put a mark on Lai’s back. Lai is used to making enemies. He has received death threats, his house has been firebombed and he once returned home to find a skinned dog on his doorstep, a “gift” that was interpreted as a warning from Taiwan’s gangs. His right-hand man, Mark Simon, once spent several nights sleeping in a van outside Lai’s house with a baton. All this has taken its toll on his family. He has six children, several grandchildren and a wife, Teresa, who is credited with his conversion to Catholicism in the late 1990s. His two eldest sons were arrested in 2020, accused of conspiracy to defraud and collusion with foreign forces, while Sebastien, his second-youngest son, has taken on the unwanted position of full-time campaigner for his father’s release from prison. Part of Sebastien’s strategy has been to appeal to western governments to put pressure on Hong Kong. He has stressed that his father is a British citizen and says that the UK government’s response has been “incredibly disappointing”. (James Cleverly, the foreign secretary, said that he raised Lai’s case on a recent visit to Beijing, although he has declined to meet with Sebastien.) Although Lai is a British passport holder, political leanings have brought him more friends among US Republicans than on British soil. Lai’s admiration for the heroes of free market ideologies are well documented. He once accompanied his friend Milton Friedman on a trip to China, where he recalled Friedman responding to a sex worker at their hotel with a one-hour lecture on the inevitability of market forces. He had busts of Friedman and Friedrich Hayek on display in his office in Hong KongSimon, a close aide to Lai for more than 20 years, describes his former boss’s approach to problem-solving as follows: “Close your eyes and feel your way. Every once in a while, you’re going to bump into a chair and hurt your knee. But just keep going.” And so in 2019, as pro-democracy Hong Kongers were protesting with increasing desperation against the tightening grip of the CCP, Lai flew to Washington to plead his city’s case in the White House. In July he met Mike Pence and Mike Pompeo, then the vice-president and secretary of state, to discuss the proposed extradition bill that was causing widespread anger and fear in Hong Kong. The move prompted outrage from Beijing, which said that the meetings were an attempt at “collusion by forces in and out of Hong Kong to destabilise the city”. But Lai was undeterred. In 2020, he was a vocal supporter of Donald Trump in the presidential race against Joe Biden, writing that Trump offered “a stronger sense of security”. Like many of the uber-wealthy, Lai’s life is a portfolio of international affairs. He has homes in Hong Kong, London, Paris, Taipei and Kyoto, and spent a reported $73m on a group of luxury hotels in Niagara-on-the-Lake in Canada, which is managed by his twin sister. And his business dealings have long been intimately entwined with his media empire. Royston Chow, a former executive at Next Digital, was, until June 2020, a director of the company that owns the Canadian hotels (and Simon, Lai’s former aide, still is). Lai, Chow and another Next Digital executive were arrested and charged with fraud relating to a minor lease violation in December of that year; Chow avoided prison by testifying against his former boss. Chow will also be a prosecution witness in Lai’s national security law trial, which is currently expected to start in December. If convicted, which is all but guaranteed with a panel of judges handpicked by the chief executive, he faces life in jail. His supporters desperately want him released, both as an old man with a family who miss him, and as a lodestar of Hong Kong’s golden era when a child refugee could become one of the city’s richest men and fiercest advocates. But for all his international links, Lai always knew this day was coming, and chose to stay. He has said for years that he was ready to go to prison for his beliefs, even as he warned friends to leave Hong Kong in the wake of the national security law. Sebastien hopes that, if nothing else, his father will be remembered as a “bright spot” in Hong Kong’s history. For Lai, although the city has changed, it is still the place that has given him an extraordinary life. As a child, he imagined Hong Kong as a place of “free, well-fed, happy people … where there was endless milk, honey, glutinous chicken rice and barbecued pork buns”. In a book he wrote about his life that was published in 2007, titled I am Jimmy Lai, he described Hong Kong as a city that made him feel “immortal”. “I used to feel sorry for this place,” he marvelled, “but now I am full of longing for its future. How could I have no passion for this place?”