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He Fought for Freedom. Then He Chose Prison.
Under solitary confinement, Chinese dissident Jimmy Lai is incarcerated in Stanley Prison in Hong Kong. (Anthony Wallace via Getty Images)

He Fought for Freedom. Then He Chose Prison.

When the Chinese Communist Party came for Jimmy Lai, the billionaire stayed put. ‘I called my people to fight. I can’t let them down.’

Jimmy Lai is one of the most important political prisoners of our age.

The 76-year-old Hong Kong billionaire has been an outspoken critic of the Chinese Communist Party for three decades. In 1995, he founded Apple Daily, the popular Chinese-language newspaper that railed against the authoritarianism of Beijing, until its bank accounts were frozen in 2021. In the intervening years, Lai was a fixture at pro-democracy protests, from the Umbrella Revolution of 2014 to the Water Revolution of 2019. He’s been tear-gassed. His home has been firebombed. And four years ago, on New Year’s Eve, he was jailed.

Since then, Lai has been in solitary confinement, in a maximum security prison at the very edge of Hong Kong. He has been charged with both publishing seditious content and foreign collusion. The trial is ongoing; Lai testified two weeks ago.

Among the human rights activists calling for his release is his former colleague, Mark L. Clifford—who served on the board of Lai’s media company, Next Digital, until it, too, was forced to close in 2021. Clifford is now the leader of The Committee for Freedom in Hong Kong Foundation—an organization dedicated to freeing the city’s political prisoners—as well as the author of a brand-new book published this week, called The Troublemaker: How Jimmy Lai Became a Billionaire, Hong Kong’s Greatest Dissident, and China’s Most Feared Critic. We’re proud to bring you an excerpt of that book today.

The Troublemaker begins with a short foreword by Free Press hero Natan Sharansky—who himself spent nine years as a political prisoner in a Soviet gulag. He had several conversations with Lai in late 2020, when the latter knew he was about to be arrested; Sharansky asked him, “Why won’t you try to escape?” It was more than possible: Lai is rich enough to charter a private jet, and he has British citizenship. “I can’t do it,” Lai answered. “I called my people to fight. They look at me. I can’t let them down.”

Sharansky writes that Lai “asked how to cope with isolation, uncertainty, and fear when the heavy doors closed behind you. This brave man hardly needed any advice. What I learned from hard experience, he grasped instinctively”—which is this: “While your body may be shackled in prison, your spirit can be free.”

Lai is keeping a diary in prison, and some of the entries have been smuggled out—revealing that Lai’s spirit does indeed remain free, even as his body is trapped behind bars. In the following essay, Clifford draws on Lai’s accounts, to shine a light on life as a political prisoner under a brutal regime. —The Editors

Jimmy ​​Lai cannot communicate freely. He sees his family between two and four times a month for 30-minute monitored visits. His friends can only see him during his court appearances. Cameras are not allowed in the courtroom, so few photos of Lai have been seen since the end of 2020. His mail is censored and limited. Because he is a symbol of Hong Kong resistance, authorities want to erase him.

But Lai has documented his time as a political prisoner in diary entries, written in English with a pencil. Some of them have been smuggled out, and they paint a vivid portrait of life behind bars.

Lai’s days in Stanley Prison have the structure and simplicity of a Benedictine monk. He wakes early; he spends his day reading, meditating, and drawing, in addition to performing mandatory prison labor. “The way I think of prison for him is that he is living a monastic life,” said Bill McGurn, now a Wall Street Journal editorial board member, who regularly corresponds with him. Lai understands that his task is very simple: He must survive with dignity. He must remain mentally and spiritually free, and remain true to his principles.

Lai had long harbored artistic ambitions—and in prison he often draws for hours each day, producing hundreds of colored pencil drawings of religious figures. (Lai is Catholic.) In one diary entry, he pronounces himself “really pleased” with a “beautiful portrait of the Holy Mother”—and plans to send the picture to his wife, Teresa.

After a judge found Lai guilty of civil disobedience charges in April 2021, he traded the gray uniform of a prisoner held without bail for the brown uniform of a convict. Conviction also brought with it a work requirement. Lai, who is worth over $1 billion, makes envelopes. He is required to make 600 a week. For this, he earns wages of $25.64 for the month, about one penny per envelope.

He spends a good deal of time trying to do this task quickly so that he has more time for his drawing. “My goal is 150 per hour,” he writes. “It is good to have a goal, so I’m always alert and trying. It is not just about reaching the goal. It is keeping hope. You hope for what you do not have. Each act of hope is one’s free act.”

With temperatures that top 90 degrees and humidity levels occasionally registering 100 percent, inmates at Stanley Prison often struggle to sleep. In late May 2021, the beginning of his first hot season in jail, Lai writes about applying for an extra tin of baby powder each month, to help. “In hot weather, without air con, your body sticks to the cloth, and at night when you turn your body, the straw mattress sticks and turns with your body. Baby powder is indispensable.” He observes, humbly: “Living in an air-conditioned world outside, I never knew about baby powder.” A few days later, Lai celebrated recent rains for breaking the heat wave and cooling the cell (“made life so much easier”). “But the guard warned me, after the rain the mosquitoes would have a field day and ‘feast on you.’ ”

Prison is designed explicitly to humiliate and to dehumanize prisoners. From the moment he wakes, Lai is reminded that his jailers are in charge. Prison regulations prohibit clocks and watches. Waking in the predawn dark on June 28, 2022, a guard told Lai it was 4:30 a.m. “I asked him to turn the light on for me and he said ‘no,’ ” writes Lai. “So I started my morning stretching exercise and ate my morning orange.”

“While I was cleaning up, the guard came and switched the light on for me, as if his conscience revoked his earlier decision not to help me,” continues Lai. “I was touched by his sympathetic help.”

​​Lai’s prison writings are filled with empathy for the prison’s guards. On one occasion, a guard hurries Lai, urging him to stop what he was doing in order to meet a visitor. Reflecting on the occasion, Lai writes: “I lost my temper at the guard. ‘I’m a prisoner—that doesn’t mean I’m not a human being!’ ”

“He kept quiet and seemed to be intimidated by my tantrum,” Lai continues. “I was sorry. I should not let off my temper. I turned to him and, in a contrite manner, held my hand out to shake his hand and apologize. He was surprised and smiled.”

Lai knows that the guards are victims of the same system that imprisons him; he records them joking that, “We are prisoners from 7 a.m. to 7 p.m.” Reporting to work, they must surrender their cell phones and subject themselves to searches. They enter the cell blocks with only their uniforms. “If any of us do anything extra nice to you,” one guard tells Lai, “never say it to anyone or you would get him into trouble.”

Prison conditions can magnify the discomfort of even minor pains and illnesses. Lai contracted a cold in late October 2022. He noted: “had little sleep. . . . My bones are aching. I still have to sleep during the day today. I shall ask officer for permission later.” Prison strips away individual autonomy—an ailing Lai must ask simply to take a nap during the day. He’s not complaining, just stating the fact.

Prison food caused constipation, which led Lai to obtain laxatives, only to be charged for possession of three unauthorized pills. Lai had to go to a prison court—with no lawyer to defend him, a guard as a prosecutor, and a superintendent trying to look like a judge (“with a wooden face and a judge’s solemnity—quite comical”). Lai received a five-day sentence mandating no snacks or soft drinks, and no newspapers, radio, or books, except for religious ones.

And then there are his actual court appearances. Samuel Bickett, a former corporate lawyer who worked for Bank of America in Hong Kong and was jailed on political charges in 2019, described how courtroom days begin for prisoners: “They do everything they can to make it very difficult. They wake you up very early, you have to eat quickly standing up, they scream at you to hurry up.”

Prisoners are strip-searched, and chained for transport. “When they finally put the chains on, you say, ‘thank goodness,’ ” said Bickett. “Putting the chains on you means they’re about to take you out to the bus and get you moving to court.” Prison buses are air-conditioned: “They were the nicest place I sat in for months,” remembered Bickett.

The Chinese Communist Party usually gets its way in Hong Kong through quiet intimidation, often by threatening someone’s job or their parents. Lai refused to put his business interests above his belief in freedom. Now he is forcing the CCP to reveal its ruthlessness to the world. Yet despite four years locked away, Lai is guilty of nothing but optimism. “He doesn’t feel the injustice” of his captivity, marvels his wife, Teresa. “He is so free. It is incredible.”

Sometimes, news from the outside world gets through to Lai. He describes reading an anonymous newsletter written by a 26-year-old Hong Konger who lives in New York. “Her strong love for Hong Kong and her unflinching determination to fight for her home is so admirable it moved me to tears,” Lai writes. “Hong Kong has such young and talented people determined to fight for us. We have hope.”

Mark L. Clifford is president of the Committee for Freedom in Hong Kong Foundation, an organization dedicated to democracy, human rights, and the rule of law for the people of Hong Kong.

This is an edited excerpt of The Troublemaker: How Jimmy Lai Became a Billionaire, Hong Kong’s Greatest Dissident, and China’s Most Feared Critic by Mark L. Clifford. Copyright © 2024 by Mark L. Clifford. Reprinted by permission of Simon & Schuster, Inc. All rights reserved.

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