Jimmy Lai has led many lives. An impoverished factory worker, a garment billionaire, owner of one of Hong Kong’s most influential papers, a born-again Catholic. He’s a man of mythical status; someone who doesn’t know their official birthday, who left Mao’s China spurred on by the taste of chocolate, who once lived in a house with a pet bear, monkey and flying fox. A son, a brother, a husband, a father, a boss, a friend. He is all of the above. But to many today he’s known mostly as a political prisoner, and not just any prisoner – arguably the prisoner the Chinese Communist Party (CCP) fears the most. 

“The more I was forced to think about Jimmy in a larger historical context, the more convinced I am that there is nobody in the 75 years of CCP rule like Jimmy,” said Mark Clifford, the author of The Troublemaker, a new biography on Lai.  

“He’s got three things that make them afraid of him,” Clifford continued. “They are: money, which means he can buy the best lawyers; a megaphone in the form of media; and principles. That may be the hardest of them all to deal with – because they don’t [have principles] right?”

Lai has been in custody since December 2020. In the years leading up to his arrest, he became a constant thorn in China’s side. In stark contrast to other tycoons who rose to the top in Hong Kong, he was one of the fiercest critics of the CCP and a leading figure campaigning for democracy in the former British territory, championing freedoms through his publications, his writings and his on-the-ground activism. This earned him the status of hero to many in Hong Kong, but the CCP branded him a “traitor” who threatened Chinese national security. 

I’m chatting with Clifford a week after the launch of his book in London, and a few weeks after it was released in the USA, which is where he has flown in from. A journalist by training, Clifford lived in Hong Kong for decades from the late 1980s, and now leads the Committee for Freedom in Hong Kong Foundation, which campaigns for political prisoners specifically and for the improvement of rights in Hong Kong more generally. 

Clifford is the obvious biographer of Lai, having known him since the early 1990s and having also served on the board of Next Digital, Lai’s media company. And it’s clear from Clifford’s book that he’s a big fan of Lai’s. That’s not to say the book is a hagiography. Clifford does recall Lai’s mistakes. He explained that he wanted to show Lai how he was and is, “warts and all”, and this makes the book a valuable addition – it’s a portrait of the man himself, rather than the symbol he has become.  

Still, there is no denying, as Clifford told me, that it’s a “portrait of a genuinely heroic person”. 

“The Chinese have been battling with him for 30 years. Every other business person has cracked, right? Everybody surrenders,” said Clifford, circling back to Lai’s defining qualities of strength and principle. 

Of Clifford’s many memories (which include when Lai cooked for Clifford – an unusually down-to-earth gesture for a man of such wealth – and many trips on Lai’s boat), one of the most vivid is a dinner at Clifford’s own house straight after an infamous column of Lai’s from 1994. In it, he described then Chinese premier Li Peng as a gui dan – turtle egg. Beijing did not take the slight lightly – they closed down Lai’s Beijing store. At dinner, Lai spent the entire evening talking about it, how corrupt the CCP were and how they had to go.

“He was quite defiant. He just felt so passionately,” said Clifford.  

It’s easy to point to several moments in Lai’s life and declare them the turning point. The protest movement and crackdown in Tiananmen Square in 1989 is one, when Lai’s garment factory supplied t-shirts to the protesters. Clifford sees his column in 1994 as another. Lai’s response was to write a follow-up piece in which he apologised for the bad language used in the first while highlighting that he still meant every word. 

In The Troublemaker Clifford paints a picture of Lai as an outsider – an immigrant who wasn’t born into money and didn’t always easily fit in with the company he kept – and this was perhaps part of his success. 

“It [his background] excluded him, but it also gave him a power, because it meant he could play by his own rules.”

He was always a natural entrepreneur, knowing what and how to sell and as he became more political his ambition became more focused: 

“He had a product – democracy – which he wanted people to buy,” said Clifford, talking of Lai’s pro-democracy newspaper Apple Daily, which blended high-brow and low-brow content to help the message travel further. 

As defiant as Lai might be, he is not unflappable. Clifford remembers a time he saw him break down in tears. Lai was giving a speech ahead of the Hong Kong handover in 1997 and it was then, to Clifford’s own knowledge, that Lai first spoke publicly about his concerns that he could be arrested.  

“On the one hand, you’re thinking ‘come on, this can’t really happen’, because it seems so unreal. On the other hand, Jimmy Lai probably has a better sense of what could happen. So he was right. He did get an extra 20-something years of freedom, but, you know, he was right,” Clifford said on reflection. 

In 2020 Hong Kong authorities passed the National Security Law. Many of those who had been heavily involved in the protest movement left Hong Kong. Lai did not. He was arrested twice that year and has not seen a day of freedom since. 

His national security trial started at the end of 2023. He is now 77 and has diabetes. And yet despite the years in prison – the bulk of which he has spent in solitary confinement – and his poor health, when Clifford has watched him during his court appearances, he remains defiant.

“It seems like he’s giving as good as he’s getting. It’s really remarkable,” he noted. 

Lai’s Catholic faith is part of the reason. He believes that no suffering is meaningless and has found refuge in faith. From his cell, he writes letters and sketches illustrations, often drawing on religious symbolism. A few years ago, a series of these were published in our magazine. 

Clifford’s book is about Lai, which means it’s ultimately about Hong Kong, a city that Clifford tells me he loved as soon as he saw it. Arriving there in the late 1980s, Clifford was drawn to it as “a place of incredible freedom”. Even though today that freedom has gone, Clifford has not foregone all hope. He holds onto the belief that economic growth ultimately leads to more freedom. “Bread is not enough,” he said in no uncertain terms.

He used the conjunction “when” Lai gets out of prison rather than “if”, and told me how I’ll meet Lai one day and he’ll thank me and everyone who has helped get him out. As for this book, it’s one of Clifford’s many contributions to that effort. Of course the CCP will hate it but, like the book’s protagonist, Clifford has little time for what the CCP thinks. 

“If the price of Jimmy getting out is that they pulp the book, that would be fine,” he said. 

The Troublemaker: How Jimmy Lai Became a Billionaire, Hong Kong’s Greatest Dissident, and China’s Most Feared Critic was published in hardback in the USA in December 2024