Jimmy Lai’s conviction was years in the making.

In the first part of his life, Jimmy Lai rose from refugee from mainland China and child laborer to owner of a casual wear 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 for his refusal to back away from defending those rights.In December, judges in Hong Kong convicted him of two counts of conspiracy to collude with foreign forces and one count of conspiracy to publish seditious material. He had pleaded not guilty to all three counts in his landmark national security trial.His sentence will be announced on Monday. He faces a maximum penalty of life in prison.Here’s a look at how he advocated democracy and challenged leaders over the years, and why he became a longtime enemy of China’s ruling Communist Party.1940s-1980sJimmy 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.ImageJimmy Lai, circa 1960.Credit...Mark CliffordHis father attempted suicide after the family home and business were seized, and later left his family for Hong Kong. His mother was labeled a class enemy and 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 to the city, which at the time was 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.ImageAt one of his shops in Hong Kong in 1993.Credit...Gerhard Joren/LightRocket, via Getty Images1989Like 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.ImageThe Giordano T-shirt that indirectly called on Deng Xiaoping to step down.Credit...Courtesy of the Hong Kong Studies Database at Academia Sinica in TaipeiThe crackdown on the protesters inspired Mr. Lai to launch a political and entertainment weekly, Next Magazine, the following year.1994Mr. 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.1995Mr. 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.ImageThe inaugural issue of Apple Daily on June 20, 1995.Credit...Courtesy of the Hong Kong Studies Database at Academia Sinica in TaipeiHis 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 wondered if Mr. Lai would be arrested.ImageThe newspaper’s slogan of “An apple a day keeps the liars away” was also printed on souvenir watches.To promote the first issue on June 25, 1995, Mr. Lai appeared in a television in which he sat calmly with an apple on his head while shadowy figures shot arrows at him. At the end, he took the apple and bit into it.“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.1996-2013In 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.”ImageJuly 1, 1997 issue of Apple Daily.Credit...Courtesy of the Hong Kong Studies Database at Academia Sinica in TaipeiBut it and its sister publication were better known for supporting pro-democracy protests. The paper would publish cutout posters ahead of planned demonstrations.In 2003, after Hong Kong tried to pass an unpopular security law, Next Magazine ran an illustration portraying Tung Chee-hwa, the first post-colonial leader, being hit in the face by a cream pie.ImageA protester holds a poster of the Next Magazine cover of a cream pie hitting the face of Tung Chee-hwa, Hong Kong’s then-leader, during a demonstration on July 1, 2003.Credit...Dickson Lee/South China Morning Post, via Getty ImagesMr. Lai spent vast sums of his own money on political s in Apple Daily and other outlets in the lead-up to a major demonstration against the proposed law. Mr. Tung eventually resigned.Around a decade later, 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.”2014Apple Daily closely covered a pro-democracy movement that became known as the Umbrella Revolution. Protesters occupied Hong Kong’s central business district for 79 days to pressure the government to allow freer elections. Mr. Lai regularly joined the protests, and like others was tear-gassed and even briefly detained by the police.ImageMr. Lai, left, at an “occupied” area outside the government headquarters in Hong Kong in November 2014.Credit...Tyrone Siu/ReutersMr. 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.Dozens of people 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.ImageProtesters barricaded the headquarters of Apple Daily in October 2014, which led to employees using a crane to lift copies of the newspaper to trucks.Credit...Lam Yik Fei/Bloomberg2019Antigovernment protests began as peaceful demonstrations against an extradition law, and evolved into months of violent standoffs between police and protesters. Streets where such confrontations took place were 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.ImageA protester holding a yellow umbrella made by Apple Daily on June 12, 2019.Credit...Lam Yik Fei for The New York TimesMr. 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 later be used against him in his trial.2020Beijing imposed a national security law criminalizing most forms of dissent and Mr. Lai was one of its first targets.In August, Apple Daily was raided by hundreds of police officers and he was arrested, then released on bail.VideoThe police arrested Jimmy Lai and searched the newsroom of Apple Daily on Aug. 10, 2020.CreditCredit...Apple Daily, via ReutersFor the next few months, he gave numerous interviews and hosted several online chats with prominent officials. He was arrested again in December.ImageMr. Lai at home in August 2020.Credit...Lam Yik Fei for The New York TimesPlaying 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.ImageThe cards with pictures of pro-democracy figures were distributed anonymously.2021-2025The police froze the accounts of Apple Daily and arrested six editors and executives during a second raid of the newspaper.VideoThe police raided the newsroom of Apple Daily on June 17, 2021.CreditCredit...Apple Daily HK, via AFPThe 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.ImagePrinting the final issue of Apple Daily early on June 24, 2021.Credit...Anthony Wallace/Agence France-Presse — Getty ImagesIn 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.ImageMr. Lai in prison in July 2023.Credit...Louise Delmotte/Associated PressHis national security trial began in December 2023, after lengthy procedural delays, including over his legal representation. Mr. Lai, who turned 78 in December, is now thin and frail. A diabetic, his health has been deteriorating from being held in solitary confinement, his family has said.