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Hong Kong police charged the chief editor and chief executive of pro-democracy tabloid Apple Daily on Friday with collusion with a foreign country, a national security case that has sent chills through the city’s media.

On Thursday, 500 police raided the media outlet and officers were seen sitting in front of computers in the newsroom after the arrest of five Apple Daily executives at dawn on suspicion that dozens of its articles violated Hong Kong’s new security law.

Police said it charged two of the five on Friday, identified by Apple Daily as editor-in-chief Ryan Law and chief executive officer Cheung Kim-hung. The other three, Chief Operating Officer Chow Tat-kuen, Deputy Chief Editor Chan Puiman and Chief Executive Editor Cheung Chi-wai, remain under investigation.

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Police also said they would prosecute three companies related to Apple Daily for the same offence after freezing HK$18 million ($2.32 million) of their assets.

The arrests have raised further alarm over media freedom in Hong Kong and have been criticized by Western governments and international rights groups and press associations.

The chief U.N. human rights spokesperson, Rupert Colville, told Reuters on Friday the raid “sends a further chilling message for media freedom”.

The national security law imposed by Beijing in 2020 on the former British colony has dropped an authoritarian chill over most aspects of life in Hong Kong, including education and arts.

Democracy supporters flocked to buy copies of Apple Daily on Friday to protest against the raid.

The popular 26-year-old paper, which combines liberal discourse with celebrity gossip and investigations of those in power, increased its Friday press run to 500,000 copies, up from 80,000 the previous day.

‘HANG IN THERE’

In the Mong Kok district, queues formed at some kiosks at midnight, with some customers carting off hundreds of first editions on trolleys and suitcases.

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“You never know when this newspaper will die,” said one reader who only gave his last name, Tsang, because of the sensitivity of the matter. “As Hong Kongers, we need to preserve the history. Hang in there as long as we can. Although the road is rough, we still need to walk it, as there’s no other road.”

By the morning, some newsstands in central Hong Kong had already sold out. One displayed a picture of Apple’s logo with the words “Support press freedom” beneath it.

Tam, a 40-year-old banker, said he’d bought his first newspaper in 20 years after hearing about the raid.

“I don’t mean to do anything with the newspaper in my hand. It’s just for my conscience,” he said.

It was the second time police had raided the newsroom after the arrest last year of media tycoon Jimmy Lai, a pro-democracy activist and staunch Beijing critic, who owns Next Digital, which publishes Apple Daily.

The newspaper printed a similar number after Lai’s arrest in August 2020. Lai’s assets have since been frozen as he faces three charges under the security law. He is serving prison sentences for taking part in illegal assemblies.

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It was the first case in which authorities have cited media articles as potentially violating the security law, imposed after almost a year of mass pro-democracy protests.

Hong Kong officials have repeatedly said that media freedom and other rights would remain intact, but that national security was a red line.

China’s Foreign Commissioner’s Office said in a statement the national security law protected press freedom, while warning “external forces” to “keep their hands off Hong Kong.”

On Thursday night in the Apple Daily newsroom, Ng, a graphics journalist who only gave his last name, said the raid was “really a pathetic moment for Hong Kong.”

“If we can’t survive, there’s no more press freedom,” Ng said as he worked.

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