HONG KONG — The police arrived early on Monday to arrest Jimmy Lai, Hong Kong’s most prominent pro-democracy media tycoon, taking him out of his mansion handcuffed and flanked by officers.

Hours later, Mr. Lai was being led through the newsroom of his newspaper, still handcuffed, while more than 200 officers filed into the building and rifled through desks. Reporters began livestreaming video of the raid, panting as they raced to document a story unfolding in their own offices. When one asked Mr. Lai about the arrest and the raid, he replied gruffly, “How should I think about it, dude?”

Mr. Lai and his publication, Apple Daily, have long been a thorn in the side of the Chinese Communist Party for their support of the pro-democracy camp in Hong Kong. Now, Mr. Lai’s arrest under the territory’s sweeping national security law makes him the most high-profile example of the power of the new legislation to subdue the party’s detractors.

The police also arrested Mr. Lai’s two sons, who are not involved in his media business, and four executives from Mr. Lai’s company, Next Digital, including its chief executive, Cheung Kim-hung. The sweep, unusual in its scale and target, stoked concerns that the new law would be used to curb the city’s freewheeling press as part of a broader crackdown on democracy advocates.

“The police really came in a big way,” said Keith Richburg, director of the University of Hong Kong’s journalism school. “It just gives the lie to any assurances that the national security law would just target a few people involved in rioting. It’s put a chilling effect over everything here.”

Credit…Apple Daily, via Associated Press

The campaign against the pro-democracy movement, including the barring last month of 12 pro-democracy candidates from an upcoming legislative election, has drawn a global outcry.

Australia, Canada, New Zealand, Britain and the United States said in a joint statement on Sunday that they were “gravely concerned” by the disqualification of candidates and the security law.

On Friday, the Trump administration placed sanctions on Carrie Lam, Hong Kong’s chief executive, and 10 other senior officials over their roles in suppressing dissent. China retaliated on Monday by sanctioning 11 American nonprofit leaders and lawmakers, including Senators Marco Rubio and Ted Cruz.

Mr. Lai, 72, was born in the mainland city of Guangzhou and worked his way up through Hong Kong’s textile industry to build the Giordano clothing brand. He embraced democracy and publishing after the 1989 crackdown on pro-democracy protests around Tiananmen Square in Beijing, but had to sell his business when the Chinese authorities retaliated against its mainland outlets.

Mr. Lai is often denounced by Chinese officials and pro-Beijing news outlets, who have called him one of the leading forces behind the large antigovernment protests in Hong Kong.

Apple Daily is a fiercely pro-democracy newspaper that regularly criticizes the Hong Kong government and the Chinese leadership. It gives extensive coverage in print and online to the protest movement, and runs front page headlines reminding readers of when to take to the streets.

The newspaper reported Monday that the police had accused Mr. Lai of collusion with a foreign country or external elements, a vaguely defined crime under the national security law. Mark Simon, a senior executive with Next Digital, said that Mr. Lai’s two sons, in addition to facing national security charges, were also being investigated for unspecified violations of corporate law. Given the lack of involvement by Mr. Lai’s sons in Next Digital, the police actions suggest that the authorities are investigating Mr. Lai’s private investments.

Credit…Vincent Yu/Associated Press

The police said in a statement on Facebook that officers had entered a building in Tseung Kwan O, the location of Apple Daily’s headquarters, with a search warrant in order to investigate national security offenses. An Apple Daily reporter who was narrating a livestream video said that police officers had loaded bags of documents taken from the building onto a truck.

The live footage showed a tense scene in the newsroom. When an editor demanded to know the exact boundaries of the area being searched, he was shoved by shouting officers. “Remember his face,” an inspector said, raising his index finger. “If he still behaves like this, give him a warning. And if he doesn’t listen to the warning, arrest him.”

Livestream footage also showed plainclothes officers at a restaurant in the Central district owned by one of Mr. Lai’s sons. The officers loaded a crate filled with electronic devices they had seized into a private vehicle and did not respond when reporters asked if they were national security officers and whether they had search warrants.

By Monday afternoon, the police said they had arrested two more people, for a total of nine, ages 23 to 72, on suspected violations of the security law. Wilson Li, a freelance journalist who works for ITV News, was one of those arrested, the broadcaster said in a statement. However his arrest appeared to be related to activist organizing, not journalism. Another activist, Andy Li, was also arrested, ITV reported.

In the evening, the police arrested Agnes Chow, a prominent activist and politician, on suspected national security law violations of inciting secession, her lawyer said.

“I’m a bit scared,” Ms. Chow wrote in a Facebook post on Sunday that noted strange men had been standing outside her apartment in shifts. “But I believe in what I’m doing.”

Credit…Lam Yik Fei for The New York Times

In recent years, media outlets in Hong Kong have complained about the erosion of press freedom in the city. Journalists covering protests have been pepper-sprayed and detained by the police. Pro-Beijing lawmakers have called for reporters to be registered. And outlets like Apple Daily have faced advertising boycotts from companies that fear retaliation from mainland authorities.

Foreign journalists, including some working for The New York Times, have experienced unexplained delays in renewing visas, and the Hong Kong authorities have refused to renew the work visa of one Times correspondent. The Times said last month that it would move part of its Hong Kong operations to Seoul, South Korea, in response to uncertainty created by the security law.

Still, the sight of media executives in handcuffs and the police raiding a newsroom elicited a new level of fear.

“Those scenes were kind of shocking to wake up to,” Mr. Richburg said. “It’s hard to believe this is Hong Kong. It is incredible how quickly everything has changed.”

The Foreign Correspondents’ Club of Hong Kong said in a statement that the raid and arrests were “a direct assault on Hong Kong’s press freedom and signal a dark new phase in the erosion of the city’s global reputation.” It added, “Today’s events raise worries that such actions are being used to erase basic freedoms in Hong Kong.”

Mr. Lai was previously arrested in February and again in April over accusations that he had participated in unauthorized protests last year. He also faces charges for joining an unauthorized vigil on June 4 to mark the anniversary of the 1989 Tiananmen crackdown by Beijing.

Credit…Apple Daily, via Reuters

It was not immediately clear what action by Mr. Lai that the authorities were considering to be possible collusion with a foreign power.

Mr. Lai, who also has British citizenship, traveled to Washington last year and met with Vice President Mike Pence, Secretary of State Mike Pompeo and the House speaker, Nancy Pelosi, among others. The national security law stipulates, however, that it can be applied only to activities that occur after it went into force, at the end of June.

Mr. Lai previously said he believed the new law would be used against him. Soon after he first wrote about the legislation, the Communist Party-owned Global Times newspaper cited mainland experts who said his tweets had provided “evidence of subversion.”

“I have always thought I might one day be sent to jail for my publications or for my calls for democracy in Hong Kong,” he wrote in an Op-Ed article for The Times. “But for a few tweets, and because they are said to threaten the national security of mighty China? That’s a new one, even for me.”

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