In the first part of his life, Jimmy Lai rose from refugee from mainland China and child laborer to owner of a casual apparel empire, becoming a millionaire.

In the second, he made a move few tycoons would, throwing his wealth and influence into backing mass pro-democracy protests and creating a popular newspaper in Hong Kong that regularly challenged China’s ruling Communist Party.

He has always attributed his rags-to-riches ascent to the freedoms of Hong Kong. And he has paid a hefty price in his refusal to back away from defending those rights.

On Monday, judges in Hong Kong will hand down a verdict in his landmark national security trial. He has pleaded not guilty to charges of conspiracy to collude with foreign forces and conspiracy to publish seditious material.

Here’s a look at how he advocated for democracy and challenged leaders over the years, and why he became a longtime enemy of the Communist Party.

1940s-1980s

Jimmy Lai was born on Dec. 8, 1948 in Guangdong, China, to a wealthy business family shortly before the Communist Party assumed power in the country.

His father attempted suicide after the family home and business were seized, and later left his family for Hong Kong. Labeled a class enemy, his mother was sent to labor camps. Mr. Lai worked as a child porter at a railway station during years of famine. A taste of chocolate from a Hong Kong passenger inspired him to move there — still a British colony — as a stowaway on a boat in 1961. He worked his way up in the city’s garment factories, starting a knitwear manufacturing business in 1975 and then the casual clothing chain, Giordano, in 1981.

1989

Like many in Hong Kong, Mr. Lai was galvanized by students who occupied Tiananmen Square in Beijing to call for a greater say in government. Giordano printed T-shirts calling for China’s then-leader, Deng Xiaoping, to step down. (The slogan subverted a slogan — “Hello, Xiaoping” — that portrayed Mr. Deng as a man of the people.)

The crackdown on the protesters inspired Mr. Lai to launch a political and entertainment weekly, Next Magazine, the following year.

1994

Mr. Lai published an open letter in Next Magazine insulting China’s then-premier Li Peng, who was seen as a force behind the Tiananmen crackdown, and telling him to “drop dead.” The authorities closed down the Giordano store in Beijing and Mr. Lai later resigned and sold his stake in the business to focus on media ventures.

1995

Mr. Lai founded Apple Daily, a Chinese-language newspaper in Hong Kong. Covering news, entertainment and politics, the full-color, often-sensationalist tabloid grew to become one of the highest-circulation papers in the city. Its slogan — “an apple a day keeps the liars away”— was also printed on souvenirs like watches.

His decision was seen as bold, even provocative, at a time when thousands were emigrating from the city, two years ahead of its handover by the British to China. Other tycoons were careful not to fall afoul of China’s ruling Communist Party. Many speculated about whether Mr. Lai would be arrested. Still, he portrayed himself as a firebrand.

To promote the first issue on June 25, 1995, Mr. Lai appeared in a television advertisement where he sits calmly with an apple on his head while shadowy figures shoot arrows at him. At the end, he takes the apple and bites into it.

“I love the intensity of trouble,” he said in a BBC interview that year. “I think that’s great fun.”

“I believe in the media, by delivering information, you’re actually delivering freedom,” Mr. Lai said in an interview in 2020 with The New York Times.

A television ad pegged to the founding of Apple Daily, shows Jimmy Lai being shot by multiple arrows.

1996-2013

In its early years, the newspaper sometimes sided with China on patriotic topics, such as territorial conflicts with Japan over the islands known in China as Diaoyu and in Japan as Senkaku. On the 1997 handover, it struck an optimistic note with the headline “A great new era begins: Hong Kong believes there will be a tomorrow.”

But it and its sister publication were better known for their role in encouraging readers to take to the streets in political protests. The paper would publish colorful cutout posters within its pages in the lead-up to planned demonstrations.

In 2003, Next Magazine published a cover illustration portraying Tung Chee-hwa, Hong Kong’s first post-colonial leader, being hit in the face by a cream pie. That came after he tried to pass an unpopular security law.

Mr. Lai spent vast sums of his own money to publish political advertisements in Apple Daily and other outlets in the lead-up to a major demonstration that was attended by half a million people.Mr. Tung eventually resigned.

Later, in 2012 and 2013, as the opposition increasingly pushed for democratic reform in Hong Kong, posters portrayed another top leader, Leung Chun-ying, as Pinocchio and included slogans such as “I am a Hong Konger, I want real elections.”

2014

Apple Daily gave blanket and sympathetic coverage to a movement that became known as the Umbrella Revolution, where protesters occupied the roads of Hong Kong’s central business district for 79 days in the hopes of pressuring the government to allow freer elections. Mr. Lai was a regular presence at the protests. He was among those who were tear-gassed and was briefly detained by police.

Mr. Lai became the target of attacks as he and Apple Daily became more closely associated with the protest movement. Oriental Daily, a pro-Beijing tabloid, published a fake obituary in August 2014, claiming that Mr. Lai had died and that there would be no funeral. Two months earlier, the website of Apple Daily was bombarded by cyberattacks that forced it to shut down for several hours.

In October, dozens of protesters barricaded the headquarters of Apple Daily and tried to physically prevent the paper from leaving the printing press for several nights in a row. Employees used cranes to lift the newspapers into delivery trucks. A headline on the incident read: “Fearless and undaunted: Apple Daily continues to publish.”

In November, a few men dumped bags of animal organs on Mr. Lai while he was at the protest site.

2019

Apple Daily gave blanket coverage to a new wave of antigovernment protests that began as peaceful demonstrations against an extradition law, and evolved into months of violent standoffs between police and protesters, leaving streets filled with tear gas, Molotov cocktails and broken glass. Apple Daily sided firmly with the protesters, using headlines such as “the tyrannical government has fired at us” to denounce the heavy use of tear gas.

Mr. Lai also traveled to the United States to meet with politicians, such as then-vice president Mike Pence, to discuss protests in Hong Kong. These meetings, photos of which were published in Apply Daily, would be used against him in his trial.

2020

Beijing imposed a national security law criminalizing most forms of dissent and Mr. Lai was one of its first targets.

In August, Apple Dailywas raided by hundreds of police officers and he was arrested, then released on bail.

For the next few months, he gave numerous interviews and hosted several online chats with prominent officials. He was rearrested in December.

Playing cards were distributed anonymously in mailboxes in residential areas depicting Hong Kong’s “most wanted” pro-democracy figures in an apparent attempt at intimidation. Mr. Lai was depicted as the joker.

2021-2025

The police froze the accounts of Apple Dailyand arrested six editors and executives during a second raid of the newspaper.

The newspaper announced it would close a few days later after rushing out a final issue that was snapped up by readers across the city. Some supporters lined up outside the newsroom, holding up their mobile phone flashlights as the papers left the press for the final time.

In December 2021, Mr. Lai was convicted and sentenced to 13 months in prison for participating in a June 4, 2020, vigil for Tiananmen victims that the government had banned. He had already been sentenced in other cases related to the 2019 pro-democracy protests.

In 2022, Mr. Lai was given a five-year sentence after being convicted of violating the terms of a lease agreement related to his newspaper.

His national security trial began in December 2023, after lengthy procedural delays, including over his legal representation. Mr. Lai had sought to be represented by Timothy Owen, a senior British lawyer, but the authorities barred him from the case.

Mr. Lai, who turned 78 last week, is now thin and frail. A diabetic, his health has been deteriorating from being held in solitary confinement, his family has said.