Lai, who is 76, is charged with several counts of "colluding with foreign forces" -- a crime under a national security law imposed on Hong Kong by Beijing in 2020 following massive pro-democracy protests.
The case against Lai, which will see him tried without a jury, is being closely watched as a test of how many of the civil liberties the city once boasted remain.
More than 30 people have been convicted under Hong Kong's security law, but Lai was one of the most recognisable figures in the pro-democracy movement.
Lai is the first to contest the charge of "foreign collusion" -- punishable with life behind bars.
Hong Kong's crackdown has also seen police offer huge bounties for activists who fled the city, in a move that has been strongly condemned by the United States and Britain.
The most serious charges against Lai revolve around Apple Daily, which he founded in 1995 and was once Hong Kong's most popular Chinese-language tabloid.
The paper was staunchly critical of Beijing and supported Hong Kong's huge and sometimes violent pro-democracy protests in 2019.
It later called for international sanctions against Chinese and local officials.
The outlet was forced to shutter in June 2021 after authorities used the security law to raid it twice and freeze assets worth HK$18 million (US$2.3 million).
Authorities charged Lai and six former Apple Daily executives with "conspiracy to collude with foreign forces".
Lai was singled out for an additional collusion charge.
All defendants except Lai have pleaded guilty and some have agreed to testify for the prosecution.
The court on Monday will also hear a raft of other charges against Lai -- which include "seditious publication".
- World should 'pay attention' -
The United States, Britain, the European Union and the United Nations have all expressed concerns about Lai's case -- which Beijing has dismissed as smearing and interference.
Lai's son Sebastien last month told AFP the case was "an opportunity for Hong Kong to show whether they are actually rule-of-law compliant".
The world "should be paying attention to my father's case, to the case of Hong Kong", he said.
The Apple Daily owner's arrest came during the rapid erosion of press freedom and political dissent in Hong Kong, with analysts saying the trial will show whether the city's courts can rule independently of Beijing.
How judges draw the line between the concepts of advocacy and collusion will be a key issue to watch, according to Georgetown University legal scholar Eric Lai.
"It is important to observe how the court would define ordinary overseas advocacy activities as a crime," Lai told AFP.
The case was "also worth concern in terms of fair trial and due process," he added.
- 'Anti-Chinese' -
Senior Beijing and Hong Kong officials have repeatedly issued statements condemning Lai since 2019.
China's foreign affairs commissioner in Hong Kong in September accused Lai of being "an agent of the anti-Chinese forces in the United States and the West" and a secessionist.
In a post on X -- formerly known as Twitter -- Britain's foreign office said that Foreign Secretary David Cameron met this month with Lai's son, Sebastien, "to listen to his concerns for his father".
"The UK opposes the National Security Law and will continue to stand by Jimmy Lai and the people of HK," the office said on Wednesday.
Beijing blasted the meeting as a clear sign of Britain's "malicious intentions", calling Lai "a driving force behind the chaos in Hong Kong".
Hong Kong follows a common law system due to its colonial history, but Lai's case differs from how criminal trials are usually run.
He will be tried, without a jury, by three judges drawn from a pool of jurists handpicked by Hong Kong's leader.
Lai has been jailed since Hong Kong's top court denied him bail in late 2020 -- a change from the city's previous practices on pre-trial detention.
His case has been further delayed after Hong Kong authorities last year sought to bar Lai from being represented by British rights lawyer Tim Owen, citing security risks.
'Born rebel': Hong Kong pro-democracy media mogul Jimmy Lai
Hong Kong (AFP) Dec 16, 2023 -
Jimmy Lai, a jailed media tycoon and prominent critic of the Chinese Communist Party, will stand trial on Monday on internationally condemned national security charges.
The 76-year-old has been in prison for three years and faces the possibility of spending the rest of his life there.
He is the first person to contest a "foreign collusion" charge under Hong Kong's national security law, imposed in 2020 after huge democracy protests engulfed the city.
Here is what we know about Lai:
- 'A born rebel' -
A rags-to-riches millionaire, Jimmy Lai is a self-styled "troublemaker" and staunch advocate of Hong Kong's now-quashed democracy movement.
Born in mainland China, he was smuggled into Hong Kong as a stowaway at the age of 12 and as a child worked in sweatshops before he later built up the hugely successful Giordano clothing empire.
Lai established his first publication shortly after China sent tanks to crush protests in Beijing's Tiananmen Square in 1989, writing columns that regularly criticised senior Chinese leaders.
His two primary outlets -- the Apple Daily newspaper and the digital-only Next magazine -- were hugely popular in Hong Kong, mixing tabloid sensationalism with hard-hitting political reportage.
They were also among the few publications that openly backed Hong Kong's massive, and at times violent, democracy protests in 2019.
Lai was vilified in China's state media as a "traitor".
Asked why he did not keep quiet and enjoy his wealth like other Hong Kong tycoons, Lai told AFP before his arrest: "Maybe I'm a born rebel, maybe I'm someone who needs a lot of meaning to live my life besides money."
- Bail denied -
He was first arrested in August 2020 when Hong Kong police raided Apple Daily and paraded him through the newsroom.
A judge briefly granted him bail in December 2020 on steep conditions, including posting HK$10 million ($1.28 million, but that lasted only a week before the top court ordered him back to prison.
He has been there ever since, with his son Sebastien Lai calling him "the oldest political prisoner in Hong Kong".
A different, tougher set of bail rules now apply to national security cases since the reversal in Lai's case, affecting dozens of other prosecutions.
Lai, a UK passport holder, was also denied his choice of representation for his collusion trial: veteran British human rights lawyer Tim Owen.
Hong Kong courts initially sided with Lai, but Beijing responded by granting new powers to Hong Kong's leader to screen overseas lawyers in security-related cases.
The city's pro-Beijing legislature went a step further in May, passing laws requiring overseas lawyers to get special permission to join security cases.
This separate dispute will continue with another court hearing next year.
- 'A death knell' -
Lai has already been found guilty in five separate cases during the more than 1,100 days he has been in prison.
He was handed a sentence of 20 months for organising and participating in marches during the democracy protests that formed the basis of four prosecutions.
He was convicted in the fifth case of "conspiracy to defraud" for breaching the terms of an office lease. That added another 69 months to his sentence.
Separately, he tried to stop police from going through two of his cellphones, citing legal protections against searching journalistic materials, and attempted to protect his Apple Daily shareholder voting rights after the company's assets were frozen.
Lai lost both cases after High Court judges stressed the importance of national security.
He told AFP before his arrest in 2020 that Beijing's national security law would be "a death knell for Hong Kong".
"It will supersede or destroy our rule of law and destroy our international financial status," he said.
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