When the Hong Kong government arrested Jimmy Lai on Monday for alleged violations of the Chinese territory’s controversial new national security law, it dispatched more than 200 police officers to haul him in for the booking and to gather evidence.

It was a lot of manpower to arrest a 72-year-old textile entrepreneur-turned-newspaper magnate, and raid the headquarters of his Next Digital media empire. But Mr Lai is not your average Hong Kong tycoon. While most of his peers readily do Beijing’s bidding, the self-made billionaire has been an outspoken proponent of democratic reforms, and critic of China’s Communist party, for more than 30 years.

As a result, the party regards Mr Lai as its prime nemesis in Hong Kong. Welcoming his arrest this week, Chinese officials denounced him and others targeted for alleged “collusion” with foreign forces, as a “scourge that hinders Hong Kong’s stability and long-term development”.

The show of police force struck many as an attempt to intimidate the 60 per cent of Hong Kong voters who regularly cast their ballots for pro-democracy candidates in legislative and district council elections. If so, it backfired. Next Digital’s livestream of the police raid went viral and the next day’s print run of the group’s flagship newspaper, Apple Daily, was seven times bigger than normal.

Mr Lai embraces his notoriety in Beijing and harbours no illusions about the Chinese Communist party and its current strongman president, Xi Jinping. “For the party it is [about] control, control, control,” he told the Financial Times in April. “It’s very clear that China has decided to take over governance in Hong Kong . . . It is the beginning of the end for Hong Kong.”

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Over the past year he has participated in a number of peaceful but unauthorised protests sparked by a clumsy attempt by the Hong Kong government to allow, for the first time, local residents to be extradited to mainland China. Hong Kong’s Beijing-appointed chief executive, Carrie Lam, backed down after mass demonstrations against her extradition bill in the summer of 2019. But public anger simmered. Large, peaceful marches gave way to increasingly violent, youth-led protests that quickly became the most intractable challenge Mr Xi has faced since assuming power in late 2012.

Then in June, Mr Xi’s administration announced it would impose its strict, new national security law. Under its provisions, acts of civil disobedience currently punishable by relatively lenient sentences can be construed as graver offences with suspects tried on the mainland or Hong Kong. That is the legal jeopardy Mr Lai now faces.

Born in China’s southern Guangdong province, Mr Lai fled when he was 12 to then British-ruled Hong Kong during one of the most impoverished and repressive periods of Mao Zedong’s rule. Working first as a child labourer in a garment factory, he rose to become manager, and spent his year-end bonus to speculate successfully on stocks. The bankrupt garment factory he bought with his winnings expanded into a pan-Asian retailer.

Appalled when Beijing unleashed the army on peaceful demonstrators in 1989, Mr Lai founded the pro-democracy Apple Daily newspaper in the mid-1990s, shortly before Hong Kong was returned to China in 1997 as a “special administrative region” with wide-ranging autonomy, civil freedoms and an independent judiciary.

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Apple Daily quickly became a best-selling title, attracting readers with sensational scoops and exposés of everyone from senior officials to local celebrities. Hong Kong readers could not get enough of a newspaper that Chinese state media accused of playing “a critical role in instigating hatred, spreading rumours and smearing Hong Kong authorities and the mainland”.

“Next Media gave reporters more space — there was much more editorial freedom than at other places,” says Alvin Chan, a journalist with the group’s digital arm. “Jimmy Lai is a very important person in the evolution of Hong Kong media.”

He could also be a difficult boss. One former employee says Mr Lai had a habit of issuing an urgent order one day and contradicting it the next. Senior staff could be shunted into drastically different roles with little or no warning. But many of his employees and friends feel he has mellowed over recent years — a transformation some attribute to his late conversion to Catholicism and a conviction that he is doing what he was meant to do. “He was very loud and often shouted at people with foul language,” Mr Chan says. “He is much nicer these days.”

“He talks about God a lot,” a friend adds. “He says ‘this is my destiny’.”

Mr Lai, who has six children from two marriages, has been a UK national since 1996. But he has never contemplated leaving Hong Kong, and is surprised that it took over 20 years for there to be a final showdown between the party and Hong Kong’s pro-democracy camp.

Now that the battle has finally been joined, Mr Lai has no regrets. Shortly after his release on bail on Wednesday, he said in his weekly webcast that he had been moved by the supporters who flocked to the police station where he was held. “People were so excited, so loud,” he said. “I was so touched. It just reaffirms that whatever I had done wrong in the past, at least what I’m doing now is right.”

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Via Financial Times