Jimmy Lai’s evolution from Hong Kong media magnate to activist in photographs

HONG KONG (AP) – Prominent democracy advocate Jimmy Lai was a child from mainland China who became a onetime Hong Kong media magnate. Unlike other rags-to-riches tycoons who cultivated ties with Beijing, he chose to be its fiercest critic.

The 78-year-old founder of the now-defunct Apple Daily, a newspaper known for its critical reporting against the governments of both Hong Kong and Beijing, was sentenced to 20 years in prison on Monday for his conviction under China-imposed national security laws.

Here are 10 key moments in Lai’s life that show his evolution from a textile entrepreneur to one of the city’s most famous pro-democracy activists.

1989: Tianmen changed the path of the clothing chain founder

From a child laborer in a glove factory, Lai transformed himself into a clothing entrepreneur, founding the Giordano casual clothing chain in 1981.

But the 1989 crackdown on pro-democracy protests in Beijing’s Tiananmen Square changed Lai’s course. Giordano prints T-shirts in support of the student-led, pro-democracy movement. He is interested in media to convey information.

1990: The beginning of a media empire

Lai enters the world of media and establishes Next Magazine with the goal of “participating in providing freedom”.

“The more you know, the freer you are,” he said in 2024, testifying at his trial.

1994: Chinese leader insulted

After then-hardline Chinese Premier Li Peng justified the Tiananmen crackdown, Lai became mad.

He wrote an open letter calling Lee “the son of a turtle’s egg.”

China put pressure on the Giordano brand, eventually forcing Lai to sell his stake in the company.

1995: Apple Daily

Two years before Hong Kong, then a British colony, returned to China, Lai started Apple Daily.

Advertisement for a tabloid-style publication stars Lye, aiming an arrow and cutting an apple. The ad ends with the magazine’s slogan, “An apple a day keeps a liar away.”

Apple Daily is seen by some as a voice of democracy and freedom, with its sometimes sensational reports and strong following with investigative scoops.

2003: Opposition to the Security Bill

Apple Daily has taken out posters in support of mass protests against proposed national security laws on the sixth anniversary of Hong Kong’s return to Chinese rule. The poster reads “Tung Chi-hwa not wanted”, referring to Hong Kong’s first Beijing-backed city leader since the 1997 handover.

Demonstrations drew an estimated half a million people to the streets of Hong Kong, and the government later withdrew the proposed legislation.

2014: Lai joins the Umbrella Movement

Lai joins pro-democracy protests against proposed electoral reforms that lack full democracy. Outside government headquarters on September 28, he wears goggles that are common safety gear among protesters. Protesters blocked police pepper spray with umbrellas, leading to the demonstration known as the Umbrella Movement.

After 79 days of occupying the road, the police cleared the protest site. Before being taken away by the police, Lai says, “I want true universal suffrage.”

2019: Meeting with US officials angers Beijing

Lai again joined the street protests.

After protesters ransacked and vandalized the legislative building on July 1, Lai suggests to his newspaper colleagues to report on the thinking of the young protesters to gain sympathy for them.

He has also met US Vice President Mike Pence and Secretary of State Mike Pompeo, angering Beijing.

2020: Lai arrested on charges of collaborating with foreign forces

Police arrested Lai on charges of colluding with foreign forces under a national security law that Beijing considers essential to the stability of the city. The media tycoon is the first major figure to be indicted.

Officers raided his media company, sending shock waves through Hong Kong’s news industry.

2021: Apple daily shutters

The newspaper has been forced to close after authorities arrested top executives and editors, and froze some of its assets. The police also raided his office.

The last edition of Apple Daily sold over 1 million copies.

2025: Punishment under National Security Law

Lai has been in custody since December 2020.

After a 156-day trial, three government-trial judges convicted Lai of conspiring with foreign forces and conspiring with others to publish seditious articles.

His ruling raises concerns about the city’s erosion of press freedom and criticism of foreign governments. The Hong Kong government claims his case has nothing to do with media freedom.

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Moritsugu reported from Beijing.