[6] A prominent critic of the Chinese Communist Party, who met with U.S. Vice President Mike Pence, Secretary of State Mike Pompeo, and National Security Advisor John Bolton in July 2019 during the Hong Kong protests,[7] Lai was arrested on 10 August 2020 by the Hong Kong police on charges of violating the territory's new national security law,[8][9][10] an action which prompted widespread criticism.

[25] In 1975, Lai used his year-end bonus on Hong Kong stocks to raise cash and bought a bankrupt garment factory, Comitex, where he began producing sweaters.

After his arrest under National Security Law in August 2020, Lai tried to sell his asset in Hong Kong, including the entire floor of Tai Ping Industrial Centre.

[30] In 1997 Lai put up the capital for his twin sister, Si Wai, to acquire numerous properties in the Southern Ontario wine and vacation region of Niagara-on-the-Lake.

[39] In 2014, leaked documents showed Jimmy Lai paid former US deputy defence secretary and former World Bank president Paul Wolfowitz US$75,000 for his help with projects in Myanmar.

[41] His best-selling Next Magazine and Apple Daily newspaper featured a mix of racy tabloid material and news items oriented to the mass market with plenty of colour and graphics that attracted a wide range of readers, some of whom were also critics of Lai and his ideology.

[45] In 1995, as the Hong Kong handover approached, Lai founded Apple Daily, a newspaper start-up that he financed with $100 million of his own money.

[49] In addition to promoting democracy, Lai's publications often ruffled feathers of fellow Hong Kong tycoons by exposing their personal foibles and relations with local government.

[50] In 2003, ahead of the record-breaking pro-democracy protests in Hong Kong during July, the cover of Next Magazine featured a photo-montage of the territory's embattled chief executive Tung Chee-Hwa taking a pie in the face.

[53] Lai launched Taiwanese editions of Next Magazine in 2001 and Apple Daily in 2003, taking on heavily established rivals who made considerable effort to thwart him.

[25] The ban originated from Lai's 1994 newspaper column, where he told Premier of the PRC Li Peng, seen as a driving force behind the Tiananmen Square crackdown, to "drop dead".

[63][64] In 2020, Apple Daily published a falsehood-ridden 64-page report produced by Typhoon Investigations alleging Joe Biden's son Hunter had a "problematic" connection with the Chinese Communist Party, which was widely cited by far-right influencers such as Steve Bannon.

[65][66][67] An NBC News report linked the Typhoon Investigations to a fake "intelligence firm" and claimed that the author of the document, a self-identified Swiss security analyst named Martin Aspen, was a "fabricated identity".

[70] Lai admitted on 25 November 2024 that he told Cheung Kim-hung about featuring more negative news in an English edition of Apple Daily, which was launched in May 2020, about a month before the enactment of the Beijing-imposed security law.

[76][16] As the proprietor of one of few that journals that has remained staunchly supportive of the pro-democracy cause, challenging Chinese Communist Party rule, Lai is considered an "anti-China troublemaker".

[82][83] Lai's aide and Next Media spokesman Mark Simon condemned these attacks and stated, "This is a continual effort to intimidate the press in Hong Kong.

[85] During the early hours of 12 January 2015, two masked men hurled petrol bombs at Lai's home on Kadoorie Avenue in Kowloon Tong.

[80] Between July and November 2019 Lai was able to meet with US Vice President Mike Pence and later with US House Speaker Nancy Pelosi to discuss the Hong Kong protests.

Bloomberg reporter, Nicholas Wadham tweeted that the meeting was meant to send a signal to Beijing, as it was very "unusual for non governmental visitors to get this kind of access".

According to a police statement, his arrest was based on suspicion of organising, publicizing or taking part in several unauthorized assemblies between August and October 2019.

The Hong Kong and Macao Affairs Office, an agency of mainland China, welcomed the arrest and called for Lai to be severely punished.

[116] In May 2021, Lai's assets were all frozen by the Hong Kong government, including all the shares of Next Digital Limited and the property and local bank accounts of three companies owned by him.

[120] A documentary about the political activism of Lai was released by the Acton Institute in 2022 to significant critical acclaim[independent source needed] called The Hong Konger.

Wall Street is so focused on making profits, the documentary points out, that it ignores blatant human-rights violations committed by the Chinese government against the Uyghurs, Tibetans, and the Hong Kongers.

"[123] In late 2022, Paul Lam and the Department of Justice made several appeals to the court system, in an attempt to disallow Lai from using a UK lawyer, Tim Owen.

[133] In September 2024, a group claiming to be Lai Chee-ying's international legal team (comprising four members from Doughty Street Chambers[134]) stated that they had submitted an urgent complaint to the UN Special Rapporteur on Torture.

The complaint alleged that Lai Chee-ying receives only 50 minutes of outdoor exercise daily in prison, lacking necessary physical activity and sunlight exposure.

The statement also noted that Lai is aware he can receive Holy Communion through special arrangements with the Correctional Services Department, which requires a priest to hold a Mass specifically for him.

[144] According to Apple Daily, on a talk show hosted by former lawmaker Albert Ho, Lai said he asked the American government to sanction certain Chinese and Hong Kong politicians.

[145] The Hong Konger: Jimmy Lai's Extraordinary Struggle for Freedom[122] is a documentary film produced by American think tank Acton Institute.