But Beijing had the last laugh when the outlet was forced to shut down in 2021, its newsroom raided and assets frozen under the sweeping national security law imposed on the city the previous year. Its founder Jimmy Lai and six then senior executives were also charged under the law.
On Wednesday, Lai testified for the first time in his trial for collusion with foreign forces, with the case revolving around his overseas political contacts.
He also faces a sedition charge related to articles published in the tabloid.
Speaking in court, he refuted the idea that he had "polluted" the minds of the paper's readers.
He insisted that "the core values of Apple Daily are actually the core values of the people of Hong Kong... (including) rule of law, freedom, pursuit of democracy, freedom of speech, freedom of religion, freedom of assembly".
- 'For Hong Kong people' -
Caustic criticism of Beijing was part of the paper's DNA from the beginning.
It was founded by Lai in 1995 "as a newspaper for Hong Kong people".
The tycoon had not been especially political until the events of June 4, 1989, when he and many other Hong Kongers watched in horror as China sent tanks and troops to crush pro-democracy protests in Beijing's Tiananmen Square.
In the ensuing years, he became increasingly outspoken -- often using especially colourful language to describe China's leaders -- and his clothing brand Giordano soon found itself in trouble with mainland authorities.
So Lai sold up and ploughed the proceeds into a new endeavour: founding a media empire.
The emergence of Apple Daily coincided with Hong Kong's return by Britain to China in 1997.
As many Hong Kongers fretted about their future freedoms, Apple Daily became the voice of the city's pro-democracy, Beijing-sceptical wing.
- Scandal and sex -
Much like Rupert Murdoch, Lai carved a space out in a crowded media landscape by being brasher and louder than his rivals, combining often populist right-wing politics with ample lashings of sex, celebrity and scandal.
He also launched a brutal price war.
The tactics paid off. In just a few years Apple Daily was printing 400,000 copies a day. Lai also opened a Taiwan edition.
Its circulation diminished in later years, but it remained a voice of defiance as local media increasingly began to self-censor and avoid taking on China's leaders directly.
As Hong Kong's pro-democracy movement gathered steam from 2014 onwards, Lai became Beijing's public enemy number one, with state media routinely describing him as a "traitor".
Apple Daily's support for the huge and sometimes violent democracy protests that rocked Hong Kong in 2019 infuriated Beijing further.
- 'Painful farewell' -
In an interview with AFP shortly before the security law was enacted in 2020, Lai predicted it would be used to silence his newspaper.
"Whatever we write, whatever we say, can be subversion, can be sedition," he said.
In June 2021, more than 500 police officers raided the paper's newsroom over what authorities said were articles and columns appealing for sanctions against China.
The paper's assets were frozen, crippling its ability to continue operating.
Apple Daily put out its last edition on June 23, ending the paper's 26-year run.
Its final front page featured one of its own journalists waving goodbye to hundreds of supporters on the streets outside.
"Hong Kongers bid a painful farewell in the rain: 'We support Apple Daily'," the headline read.
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