The Troublemaker: How Jimmy Lai Became a Billionaire, Hong Kong’s Greatest Dissident, and China’s Most Feared Critic. By Mark L. Clifford. New York: Free Press, 2024. 288 pp.
Mark Clifford’s The Troublemaker is an insider account of the jailed Hong Kong media tycoon Jimmy Lai’s trajectory from child refugee to successful entrepreneur to democracy activist. Clifford served on the board of Lai’s media company, Next Digital, and hosted his daily livecast with politicians, activists, and academics from around the world during the mogul’s last few months of freedom.
The 77-year-old Lai — founder of the now-shuttered Apple Daily, the top-selling Hong Kong newspaper known for its prodemocracy, anti–Chinese Communist Party (CCP) stance — was arrested in mid-2020 under the Beijing-imposed National Security Law. He was granted bail but arrested again in December 2020 and has been imprisoned since late that year. At the time of this writing, he is on trial for “conspiring to collude with foreign forces” and “conspiring to publish seditious materials” in Apple Daily. He faces up to life imprisonment on top of the nine years and eight months he has already received for other drummed-up charges.
In the book’s foreword, Natan Sharansky, a Soviet dissident who spent nine years in a gulag, compares Lai to Alexei Navalny, the Russian anticorruption activist and political dissident who died in an arctic prison in March 2024. Sharansky addresses the often-asked question: Why did Navalny return to Russia after multiple assassination attempts, knowing that he was certain to be arrested? He was not “fighting for his survival,” Sharansky writes, but “for the future of his people.” Navalny wanted Russians to know that he was “not afraid of Putin” and nor should they be. His “life and his message inspire millions” (p. xiv). Substitute Lai for Navalny and you immediately grasp why Lai did not leave Hong Kong despite the risk of spending the rest of his life in prison or worse.
Lai is willing to give everything for Hong Kong because Hong Kong made him who he is today. He spent his early childhood in China on the streets while his mother was in and out of labor camps during the Anti-Rightist Campaign and Great Leap Forward of the 1950s and 1960s for having “wealthy in-laws and a businessman husband who had fled to Hong Kong” (p. 12). In 1961, when Lai was twelve, he convinced his mother to let him find a better life in Hong Kong and stowed away on a fishing boat with only a dollar in his pocket. Upon arriving in the city, he found work, and a place to sleep, in a garment factory. In 1975 at the age of 27, Lai bought the bankrupt knitwear manufacturer Comitex. Six years later, he founded the fast-fashion chain Giordano.
But Lai’s is not the usual rags-to-riches story. Few other Hong Kong tycoons would dare speak out against Beijing as Lai has. “Jimmy and I were the only two guys,” said fellow businessman and antigovernment activist Herbert Chow, who fled the city in 2023 to avoid arrest. “We looked to the left and looked to the right and we only saw each other” (p. 180).
Clifford’s biography of Lai has shown me that if Hong Kong made Lai who he is today, then Lai made Hong Kong what it was yesterday — that is, the free Hong Kong that we once knew, but is now gone. Those of us who were born and raised in Hong Kong in the 1960s and 1970s, who called it home, put down deep roots, and would become the cornerstones of future social movements, grew up not believing that it was “a borrowed place on borrowed time.” The Troublemaker makes me realize, however, that Hong Kongers’ fight for democracy really did operate on borrowed time: Beijing was determined to deny democracy and kill our freedoms. As Tiananmen protesters fought for economic and democratic reforms in 1989 and the handover of Hong Kong from Britain to Beijing drew closer, the slogan “Today’s Tiananmen, Tomorrow’s Hong Kong” captured “the worries of a city where almost every family had someone — a father, a mother, an aunt, or an uncle — who had fled from communist rule on the mainland” (p. 61). Nervous about their own impending “deadline” in 1997, Hong Kongers fervently supported the Tiananmen protesters (p. 59).
From then on, Chinese authorities would view the city as “a subversive fifth column” and “an existential threat” (p. 153). Lai believed that Hong Kong “inherited Western culture and values and institutions,” including “rule of law, private property, freedom of speech, of assembly, of religion” (p. 116). But the CCP was never willing “to accept that Hong Kong people genuinely wanted liberty or democracy” (pp. 171–72). And in 2012, after Xi Jinping came to power, Beijing’s tolerance for Hong Kong’s democracy movement vanished.
Lai’s right-hand man, Mark Simon, who was a top executive at both Apple Daily and Next Digital, saw Apple Daily as “the bulldozer” for “its take-no-prisoners, tabloid-style approach” (p. 86). Yet a more accurate analogy would have been Beijing as the bulldozer (or column of tanks) bent on flattening any freedom in its path. Lai and other prodemocracy activists (like the Tank Man of Tiananmen Square) managed to resist Beijing’s pressure for as long as possible, doing whatever they could to maximize the borrowed time between “today” and “tomorrow.”
We cannot construct a counterfactual Hong Kong in which Lai’s enterprises — clothing retailer Giordano, the weekly Next Magazine, and Apple Daily — never existed, but we can contrast the Hong Kong of before and after. Clifford situates Lai’s young adulthood in Hong Kong in the world of Below the Lion Rock (p. 28), a popular television series that first aired from 1972 to 1980, with four subsequent seasons broadcast over the last four decades. The show depicted Hong Kong residents — ordinary people, often migrants from the mainland — who pulled themselves up by their bootstraps. In Below the Lion Rock’s early years, the cityscape was shaded in muted tones, when ordinary families like mine could afford to buy only products made in China and were rebuffed in stores for looking poor or touching merchandise. But Giordano’s arrival in 1981 brought the colors of the rainbow to street stores and shopping malls, where customers were now welcome just to browse the merchandise without buying anything — a new reality that was uplifting for the working class.
Next’s debut in 1990 brought yet more color, not only in vibrant photos on high-quality paper, but also in its incisive investigative reports of the rich and powerful. Ordinary Hong Kongers were so hungry for behind-the-scenes details of elite scandals and genuine news that the magazine became addictive. Family members would fight over who got to read the latest issue first, and you would see people reading it everywhere, from the metro rail to restaurant dining rooms. When I was studying for my PhD in the United States, I begged my family to send me the magazine to help cure my homesickness.
Apple Daily came on the scene in 1995, just two years ahead of Hong Kong’s transfer of sovereignty to China. The people were anxious about what lay ahead. Among well-off families, the skeptical ones made plans to emigrate to Western democracies while the opportunistic ones were busy profiting from the expanding Chinese market. For ordinary people, whose best option was to stay put, Apple Daily provided not just sensational stories in full color but also an anchor — a sense of being in this boat together, navigating the dreaded transition. As Lai later explained: “Most of the media was so scared. . . . They all went into self-censorship. . . . All of a sudden somebody came up who didn’t care about the communist takeover and was not afraid of it. People find some strength there” (p. 84).
The Hong Kong–based writer and lawyer Antony Dapiran has called Hong Kong a “city of protest.” And it is true that in a city of six million, 1.5 million Hong Kongers demonstrated in support of the Tiananmen Square protesters in 1989. In the following years, however, many of those who had been in the streets began to “dialed back their support of democracy as the 1997 takeover of Hong Kong loomed” (p. 82). While some “troublemakers” continued to mark key dates — January 1 (New Year’s Day), June 4 (the Tiananmen Massacre), July 1 (the handover to China), and October 1 (China’s National Day) — with marches, large protests became less frequent.
Lai, however, was “jolted” by Tiananmen (p. 69): “Suddenly it was like my mother was calling me in the darkness of the night and my heart opened up” (p. 64). From then on, he would pursue a path that “publicly and defiantly put him in opposition to the Chinese Communist Party” (p. 64). Giordano printed the names of Tiananmen student leaders — Wang Dan, Chai Ling, and Wuer Kaixi — on T-shirts; and Lai himself donated tents and supported Operation Yellowbird, which smuggled dissidents facing arrest out of China. Lai came directly into Beijing’s crosshairs in 1994 when, in his column in Next, he described Li Peng, “the butcher of Beijing” who ordered the crackdown on Tiananmen Square, as a “national humiliation” and a gui dan (literally “turtle egg”), meaning someone with such a low IQ that they do not even know who their parents are (pp. 76–77). In 1995, two years before the handover, Lai published the following message in Apple Daily: “An Apple a day keeps the liars away” (p. 84). It was hardly a subtle jab at Beijing’s routine cover-ups and propaganda.
In 1994, Beijing pressured Lai to resign from Giordano and, two years later, to sell his stake in the company. But Apple Daily was going strong. The math was simple: About six in every ten registered voters had chosen prodemocracy candidates in the first elections to the Legislative Council in 1991 (p. 82). Most people “below the Lion Rock” wanted freedom and democracy, and Apple Daily gave readers what they wanted, what other newspapers were too afraid to provide.
Apple Daily was instrumental in bringing “hundreds of thousands and then millions of protesters into the city’s streets in 2003, 2014, and 2019” (p. 5) — Lai made Hong Kong the “city of protest” as we remember it. In 2003, when the authorities first wanted to introduce a national-security law, the paper published a center page designed as a ready-made protest sign for July 1 demonstrators. The campaign eventually toppled the city’s first chief executive, Tung Chee-hwa (p. 94). In 2014, when the Umbrella Movement mobilized for genuine universal suffrage, Apple Daily provided “full-throated support” and legitimized the street occupation by publishing articles highlighting the protesters’ civic engagement (pp. 155, 162). Lai even “putting his body on the line” this time by camping out on “Umbrella Square” in the Admiralty district (one of three occupation sites), so that he was among those arrested when police cleared the encampment in December (p. 160). In 2019, Lai supported a new round of demonstrations, throwing “Apple Daily into the fight against the extradition bill” (which would allow authorities to send any wanted individuals from Hong Kong to mainland China) by publicizing police brutality against the protesters (p. 165).
Beyond running articles in Next and Apple Daily, Lai personally bankrolled the prodemocracy movement (p. 3). Clifford notes how Lai contributed at least US$140 million of his personal wealth “from the time he first sold T-shirts in support of Tiananmen to the day he went to jail” (p. 95). As one exiled Hong Kong activist attested, “Without Apple Daily there would be no Hong Kong pro-democracy movement” (p. 5).
Lai always understood the risks he was facing: “It is just natural they nail me. I have . . . an opposition newspaper supporting the movement. I am very vocal opposing the Communists. I participate in every [demonstration]. For them, I am a troublemaker. It is hard for them not to clamp down on me” (pp. 3–4). In August 2020, Lai was arrested and Apple Daily was raided under the new National Security Law. In 2021, he was convicted and sentenced to 28 months in prison for participating in “illegal assembly” during protests on 18 and 31 August 2019 and to thirteen months for lighting a candle during a Victoria Park Tiananmen vigil on 4 June 2020. On 17 June 2021, Hong Kong authorities again raided Apple Daily, this time arresting Lai and other top executives, and would soon strip Lai of his ownership rights and freeze the paper’s corporate bank accounts. Apple Daily was forced to shut down on 24 June 2021. In 2022, Lai was sentenced to another five years and nine months for having sublet a small personal office at the Apple Daily building. In the latest trial in November 2024, Lai faces the maximum penalty of life imprisonment.
Family and friends who have visited Lai in prison report that he felt lost when “the Hong Kong government killed Apple Daily” (p. 194). But he has always been philosophical about the struggle that he and so many Hong Kongers have been waging. “Even if we fail,” he once reflected about the 2014 Umbrella Movement, “we should not let this period of history go by without leaving a mark. Even if we fail, we would have fought for universal suffrage, cried, and tried our best” (pp.148–49).
Lai has been in solitary confinement since December 2020, but is managing to take his internment in stride. In a conversation just before Lai went to prison, Natan Sharansky told him: “As long as I live, I will live as a free person.” Lai has taken those words to heart, and his prison writings display “a sense of freedom” (p. 114). He converted to Catholicism in 1997 and has become more devout over the course of his political battles. In jail, he maintains a monkish existence, studying Catholic theology and drawing pictures of Jesus Christ and the Virgin Mary (p. 114). Clifford concludes: “Whether in prison or outside it, Jimmy Lai Chee-ying has chosen a life of freedom” (p. 217). Let us hope that he will regain his personal freedom in his lifetime.
Copyright © 2025 National Endowment for Democracy and Johns Hopkins University Press