The rise and fall of Hong Kong's Apple Daily

This was the moment 500 officers raided Hong Kong's Apple Daily, a beacon of media freedoms on the margins of Communist China.

[Hong Kong leader Carrie Lam, saying:] "Don't try to beautify these acts of endangering national security."

It's being widely seen as a direct attack on the city's freewheeling media and has come as a shock to those concerned about the erosion of Hong Kong's freedoms.

[Columnist Edward Chin]: "... it's a political crackdown and it's also playing some sort of psychological warfare. And shame on them if this is the way they want to see Hong Kong become."

Apple Daily was set up in 1995 by Jimmy Lai, a self-made textiles tycoon who was jailed in April for joining unauthorized rallies.

The splashy Chinese-language tabloid became a runaway commercial success read by dissidents and a more liberal Chinese diaspora.

The paper features a mix of celebrity gossip, investigations of the powerful and pro-democracy editorials and is known for repeatedly challenging Beijing's rising authoritarianism.

Last year's security law was Beijing's first major move to put Hong Kong on an authoritarian path.

Apple Daily's advocacy of democratic rights and freedoms had made it a thorn in Beijing's side.

Hong Kong's police chief warned in April that media outlets that endanger national security through "fake news" would be investigated.

The newsroom began bracing for a crackdown, reporters have since told Reuters.

Most staff received cards with lawyer contacts and news materials were firewalled or sent abroad to protect information and sources.

On June 4, authorities banned the annual candlelight vigil in downtown Victoria Park to commemorate the deadly 1989 Tiananmen Square crackdown.

Apple Daily's front page the next day read: "You can close Victoria Park. But not lock people's hearts."

The raid came on June 17.

Police arrested five executives, including chief editor Ryan Law and CEO Cheung Kim-hung.

Authorities also froze $2.3 million of Apple's assets.

Three days later the paper marked its 26th anniversary with merely enough cash left for "a few weeks" of normal operations.

Some observers say the media crackdown could extend beyond Apple given China's unrelenting drive to wrest control over the city after protests in 2019.