Confined in a cell in the maximum-security Stanley Prison, its high walls and watchtowers perched above the rocky coast of Hong Kong’s Tai Tam Bay on the South China Sea, media magnate and democratic activist Jimmy Lai has come full circle.

Six decades ago, as a penniless boy of 12, he stowed away in the hull of a fishing junk and sailed over these same waters seeking haven in Hong Kong. Scrambling ashore, he “touched base” in the then British colony and was taken on as an odd-job worker at a garment factory, joining a flood of refugees fleeing famine and persecution in Communist-ruled China.

Mr. Lai, now a billionaire, credits Hong Kong’s freewheeling system – its laissez-faire capitalism, small government, rule of law, and basic freedoms – for giving him the opportunity to succeed. “Hong Kong ... made me what I am today,” he said in a speech late last year. “I came here with one dollar and the freedom here has given me the opportunity to build myself up.”

But today, for Mr. Lai and many others, Hong Kong’s beacon of liberty has dimmed. With Hong Kong no longer a safe harbor for free speech, more residents are seeking to escape, as China swiftly imposes mainland systems of authoritarian control on the territory – curtailing basic rights, silencing the democratic opposition, and jailing critics.

On Friday, Mr. Lai, long one of Beijing’s most prominent and outspoken detractors, was sentenced to 14 months behind bars for taking part in two peaceful, pro-democracy protests in 2019, during a mass movement to maintain and expand Hong Kong’s autonomy from Beijing. The same day, his trial began for alleged violations of Hong Kong’s sweeping new national security law, charges that could see him jailed for life.

Beijing has labeled Mr. Lai a traitor, a “black hand” behind the protests, and an “extremely vile anti-China element” – singling him out for censure with a handful of others. In a Friday article in the Party-run Qiushi magazine, senior Chinese officials responsible for the territory denounced Mr. Lai as the “backbone” of “chaos” in Hong Kong. On Sunday, the party mouthpiece People’s Daily hailed the sentencing of Mr. Lai and others as “the embodiment of justice.”

Mr. Lai, a Roman Catholic, knew this day was coming. As a wealthy British citizen, he had ample means to flee China once again, friends and associates say – this time for a life in exile. But he stayed. “He’s a man of integrity and sincerity. He doesn’t have to be in jail right now. He could have left the country,” says the Rev. Robert Sirico, a friend of Mr. Lai and his family for decades, and president of the Acton Institute for the Study of Religion and Liberty.

Jimmy Lai, founder of the Hong Kong newspaper Apple Daily, is detained by the national security unit in Hong Kong, Aug. 10, 2020. Mr. Lai is one of the highest-profile figures arrested under Hong Kong's new national security law.

Indeed, Mr. Lai has made clear that his choice is the culmination of political and religious convictions forged throughout his lifetime – and his overriding certainty that fighting for freedom, democracy, and the rule of law is not only essential for Hong Kong, but also for the rest of the world, as it confronts an increasingly assertive Communist Party leadership in China.

“The remarkable thing about Jimmy Lai is that he has not bowed,” says Mark Clifford, a director at Mr. Lai’s media company, Next Digital. “It's remarkable that one person has the courage to not buckle in the face of this extraordinary pressure by ... certainly one of the most authoritarian and repressive governments in the world.”

On April 3, Mr. Lai picked up a pen in prison and wrote a letter to the staff of Hong Kong’s Apple Daily, the newspaper he founded. “The situation in Hong Kong is becoming more and more chilling,” Mr. Lai wrote in the letter, published last week just before his sentencing. “It is time for us to stand with our heads high.”

Hong Kong success story

As Mr. Lai tells it, he was first drawn to Hong Kong by a taste of chocolate. Born Lai Chee-ying in Guangzhou in 1947, his wealthy family lost everything after the 1949 Communist Revolution and his mother was sent to a labor camp. At the age of 9, he was famished and working as a porter at a train station when a man tipped him with a bar of chocolate. He immediately bit in. “It was so tasteful. It was amazing,” Mr. Lai recalled in a talk years later. The man, he learned, came from Hong Kong. “Hong Kong must be heaven,” he told himself, determined to make his way there.

China was in the throes of the Great Leap Forward, a human-made disaster that saw tens of millions perish from famine, when Mr. Lai’s mother reluctantly allowed him to leave for Hong Kong in 1960. His hard work, ingenuity, and risk-taking – along with a personality that’s down to earth and a bit gruff – saw Mr. Lai rise rapidly at the garment factory. In 1981 he founded Giordano, a clothing retailer that rapidly expanded into an international chain, paralleling an economic boom in Hong Kong and China.

“He’s an archetypal Hong Kong success story,” says Mr. Clifford. Like Hong Kong, he was gregarious and pragmatic. He had a taste for collecting modern Chinese art, but never lost his common touch, say friends and colleagues. (Mr. Lai’s legal team declined a request for an interview.)

Mr. Lai taught himself English and embraced the ideas of free-market economist and liberal philosopher Friedrich Hayek, agreeing with his critique of socialism as he grew ever more troubled by Communist policies in China. Then came the euphoric 1989 student-led democracy movement in China and the brutal military crackdown on protesters in and around Beijing’s Tiananmen Square on June 4 that year.

After years of distancing himself from China, Mr. Lai was jolted into becoming an activist for democracy – and harsh critic of China’s Communist Party (CCP) leaders. Ever since, he’s backed the push for greater autonomy and freedom in Hong Kong, joining street marches and donating to pro-democracy political parties.

“He stands out as being the only really high-profile businessperson who has been unwavering in his support” for democracy in Hong Kong, says fellow activist Samuel Chu, whose father helped Tiananmen activists flee through Hong Kong to safety. “He’s not flashy,” says Mr. Chu, managing director for the Hong Kong Democracy Council in Washington. “He’s just a regular guy, who’s ready to go to jail.”

Supporters raise copies of the Apple Daily newspaper as media mogul Jimmy Lai, founder of Apple Daily, is released on bail in Hong Kong, Aug. 12, 2020.

In coming years, Mr. Lai turned his entrepreneurial skills to the media business. “You deliver information, then you deliver choice, and choice is freedom,” he told the Acton Institute years later. He launched the successful Next magazine and then, in 1995, the Apple Daily newspaper, which quickly emerged as Hong Kong’s second largest. Another paper followed in Taiwan, and he set his sights on mainland China.

The splashy Apple Daily tabloid has been criticized for a sensationalist bent. But its award-winning journalists also engaged in muckraking that shook up the Hong Kong establishment, while endorsing democratic political change and criticizing China’s leaders. “They did this with an aggressiveness that garnered him ... a lot of enemies way before the political stuff was so serious as it is now,” says Mr. Clifford.

Growing suspicion

From Beijing’s perspective, Hong Kong’s ongoing democratic activism made it a potential base for subversion against the mainland – with Mr. Lai one of the chief instigators. Hong Kong kept memories of Tiananmen alive with large annual vigils on June 4, while waging one protest movement after another against Beijing’s encroachment on Hong Kong’s autonomy, and against failures to grant more representative government as promised when China resumed sovereignty over the territory in 1997.

Beijing began shutting down mainland Giordano stores in the 1990s, and Mr. Lai sold his large stake. On the media front, his publications faced an advertising boycott by large sections of the Hong Kong business community worried about offending Beijing. Mr. Lai endured physical threats, ranging from an assassination attempt to firebombs hurled at his home; he was tailed constantly, and photographers posted outside his house documented every visitor.

But Mr. Lai and Hong Kongers refused to stop speaking out. Hong Kong’s mass protests saw millions take to the streets against a proposed China extradition bill in the summer of 2019. Pro-democracy candidates won a landslide victory in local elections that November, followed by a big turnout the following July in an unofficial primary for selecting pro-democracy legislative candidates.

In an op-ed in September 2019, Mr. Lai said Hong Kong was standing up to China’s authoritarianism and urged the United States to confidently promote individual liberty. “The world will never know genuine peace until the people of China are free,” he wrote in The Wall Street Journal, arguing against appeasement of the Asian economic giant. “In all your dealings with China ... remember we are fighting your battle.”

Then came the pandemic, and China’s crackdown on Hong Kong, which was swifter and more sweeping than Mr. Lai or many others expected. The national security law that Beijing imposed on Hong Kong was passed June 30, 2020, amid warnings from critics that it would severely erode the territory’s judicial independence. Pro-democracy legislators and activists were rounded up in waves of arrests. In August, Mr. Lai was led away in handcuffs as police raided Apple Daily. Other leading pro-democracy figures arrested and recently sentenced along with Mr. Lai include barrister Martin Lee, known as the “father of democracy” in Hong Kong, who helped draft its mini-constitution.

“These veterans have been sores in Beijing’s eyes for so long,” says Victoria Tin-bor Hui, associate professor of political science at the University of Notre Dame. “For Beijing, it’s mission accomplished. They are making Hong Kong safe for the CCP.” In March, Beijing approved an overhaul of Hong Kong’s legislative system to ensure only “patriots” could govern.

Mr. Lai’s case is setting precedents under the national security law, activists say. Charged with colluding with foreign forces – based in part on articles he wrote and interviews he gave – Mr. Lai applied for bail but was refused, in an unusual court decision for Hong Kong. “That is not by accident,” says Mr. Chu. “He is the one who said, ‘Let me be the tip of the spear.’”

“Jimmy Lai is clearly the victim of judicial harassment,” says Cédric Alviani, East Asia bureau head for Reporters Without Borders. “He’s become the symbol of Hong Kong press freedom that the Chinese regime has decided to take down,” sending a message “to all media professionals that you are not immune.”

“You cannot publish information that the Chinese regime doesn't want to be published,” he says. “This is a message that freedom of the press is not whole anymore in Hong Kong.”

Like other activists, he questions how long Apple Daily can survive, as “one of the last remaining voices of opposition to the Chinese regime.”

Hong Kong’s future

The crackdown has forced the Hong Kong democracy movement to adapt from one of vocal protest to quiet resistance, as most activists lie low, brainstorming new strategies, while a small number flee overseas to continue their struggle, says Willy Wo-Lap Lam, adjunct professor at the Chinese University of Hong Kong and an expert on Chinese politics.

Some analysts say while Mr. Lai’s choice to stay was admirable, he could have better aided the movement by escaping.

“One must admire and respect somebody like Jimmy Lai,” who’s lived under communism and knows “the party will be very harsh on him when it comes for him,” says Steve Tsang, director of the SOAS China Institute at the University of London.

“I would also say from the other side, that it was really very unwise on his part,” he says. “He could have taken most of his money out of Hong Kong and ... enabled the resistance to last much longer.”

Still, Dr. Tsang concludes, “give the man the benefit of the doubt. Whatever he is ... he is not naive.”

Many activists believe Mr. Lai’s refusal to back down personifies to the world Hong Kong’s strong spirit in resisting Beijing’s repression. “Hong Kong belongs to the world and we are not going to let this die,” says Mr. Chu. “You make martyrs of people like Jimmy and Martin and Joshua [Wong] and Agnes [Chow] and they become even more relevant and powerful.”

Mr. Lai’s decisions underscore the steadfastness of Hong Kong’s opposition, experts say. “Beijing's ... strategy seems to be, beatings will continue until morale improves. I suspect Beijing will soon discover that many, many, many beatings later, morale has still not improved,” says Alvin Cheung, a Hong Kong barrister and university lecturer now at New York University. “There's a very real possibility that there will still be acts of underground resistance.”

In his recent letter from prison, Mr. Lai wrote that he is at peace and sustained by his faith, reading the Bible, praying, and exercising daily.

In a talk last fall with the Catholic Napa Institute, he said he could never renounce his values, even if it means years in prison. “I am what I believe; if I cannot change it, I have to accept my fate with grace.”