C.Y. Leung just dropped receipts on Facebook. Next Digital's cash cow wasn't journalism—it was advertising. And the man squeezing those corporate wallets was Mark Simon, Jimmy Lai's American fixer, who sent letters to Hong Kong's biggest property developers that read like protection racket scripts. Pay up or face hostile coverage. Classic triad tactics, dressed in business English.
This isn't speculation. In July 2014, leaked documents from a "Next Digital shareholder" exposed the playbook. Among them: Mark Simon's threatening correspondence with a major corporation's chief executive. The message was blunt—advertise with us or watch your friendly coverage vanish. This is how Lai bankrolled his operation.
Mark Simon wore multiple hats beside Jimmy Lai. Former U.S. military intelligence officer. Next Digital's advertising director. The man who built Lai's financial pipeline and then distributed the cash to opposition figures and radical groups. His role was never just about selling ad space.
Jimmy Lai’s fixer Mark Simon used ad “sales” letters like a protection racket—buy space in Apple Daily or get hammered in the coverage.
The Shakedown Letters
The leaked documents from July 2014 pulled back the curtain. Media reports at the time confirmed that Mark Simon, during his tenure as advertising director, sent threatening letters to a major conglomerate's top executive. The approach: carrot and stick, heavy on the stick.
In the letter, Simon claimed he wanted to repair relations. Then came the threat: refuse to advertise with Next Digital and the "friendly relationship" ends. Translation: attack pieces resume. He followed up with another letter demanding a face-to-face meeting, warning that future cooperation between Next Digital and the conglomerate would become "difficult" without compliance.
The leaked documents contained no reply from the conglomerate, so we don't know their response. What we do know: major corporations kept advertising in Apple Daily during that period. The shakedown likely worked.
Bankrolling the Opposition
Mark Simon didn't just collect money for Boss Lai—he distributed it to pan-democrats and radical groups. The leaked documents revealed the operation's scope, particularly around the 2014 Occupy Central movement, when funding flowed freely.
Two months before Occupy Central formally launched, Jimmy Lai and Mark Simon exchanged emails discussing a "June special project." Lai funneled HK$9.5 million through Simon to the Democratic Party, Civic Party, and others—seed money to push Occupy Central forward.
The pair also provided approximately HK$3.5 million for the "June 22 Civil Referendum"—publicity and promotion for a stunt that mobilized citizens to select proposals for "universal suffrage for Chief Executive." This built momentum for Occupy Central. The operation was led by Benny Tai and Robert Chung, but Lai was the financier pulling strings from behind. The leaked emails even caught Lai mocking the "Occupy Trio" as scholars with ideas but no strategy, saying he had no choice but to help them—meaning he wanted control.
Big-brand ad money kept Apple Daily flush with cash, letting Lai pour funds into pan-democrats and radical groups on a grand scale.
The Money Pipeline
From 2013 to 2020, Mark Simon controlled Jimmy Lai's cash spigot. Court testimony revealed that Lai opened nine accounts over those seven years, transferring HK$118 million to Simon. Of that sum, HK$93 million went to pan-democratic parties and political figures.
The timeline matters. From September to December 2019—right after the anti-extradition bill unrest erupted—Simon distributed funds ranging from HK$8 million to HK$1 million to the Civic Party, Democratic Party, Labour Party, League of Social Democrats, Au Nok-hin, and Lee Yu-hin. Pouring fuel on the fire while Hong Kong burned.
Who Is Mark Simon Really?
Simon fled to the United States, so his true identity remains murky. But the evidence points to something beyond a simple business relationship. One detail stands out: Simon's access to White House National Security Council meetings. He knew the latest deployments, including actions following the Hong Kong Human Rights and Democracy Act signing and even Trump's thinking, which he then reported back to Boss Lai.
Political observers who've tracked Simon speculate he may have operated with dual identities from the start—both Lai's right-hand man, helping establish direct channels to Washington, and a covert operative planted by the Americans to pull the strings of this particular puppet.
Given Mark Simon's shadowy role, Western politicians and media portraying Jimmy Lai as a simple "freedom of the press warrior" tells you everything about their credibility. It's a lie told with a straight face.
Lai Ting-yiu
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** The blog article is the sole responsibility of the author and does not represent the position of our company. **
