The Jimmy Lai Chronicle – What the Court was told (1) The Middleman's Playbook: How a Foreign Influence Machine is Built

The 855-page court judgment is out. It exposes the mechanics of Jimmy Lai's overseas network—and the role his “assistant” Mark Simon played as fixer-in-chief. In December 2025, Lai was convicted on three counts, including two charges of conspiracy to collude with foreign forces.

The documentary evidence is damning. WhatsApp logs. Payment records. A web of connections spanning Westminster to Washington to Taipei. The American line is most elaborate, from the US President, the Vice President, the Secretary of State, the National Security Adviser, to the Speaker of the House of Representatives and the US Senate.

When defense lawyers asked Lai to explain his "overseas relationship network," he tried to downplay it: these connections "developed naturally", he said, tied to his business interests, never malicious. He claimed he had every right to befriend foreigners who shared his values. However, the judgment dismantled that narrative paragraph by paragraph, tracing payments, meeting schedules, and coordinated lobbying campaigns.

The UK Pipeline

The British connection centered on Benedict Rogers, founder of Hong Kong Watch. Lai testified that he only met Rogers after Hong Kong authorities denied Rogers entry to the city, then stayed in touch via WhatsApp. Whenever Rogers wanted to publish an article in Apple Daily, he reached out to Lai directly.

Around 2019, Lai donated £20,000 to Hong Kong Watch, calling Rogers's work "meaningful" and claiming it "supported Hong Kong".

Lai claimed ignorance about Rogers serving as an adviser to the anti-China organization “Inter-Parliamentary Alliance on China” (IPAC). He insisted Rogers wasn't acting as a foreign agent or on Lai's behalf.

Yet, Rogers and Hong Kong Watch monitored Hong Kong developments, issued criticisms, and lobbied the UK government for action. Rogers maintained close ties with UK political figures including Lord David Alton and former Hong Kong Governor Chris Patten.

Lai met Lord Alton through Rogers. On July 1, 2019, Alton gave Lai a tour of the Palace of Westminster and hosted him for afternoon tea. On November 24, 2019, when Lord Alton and Luke de Pulford—a founder of IPAC—came to Hong Kong to observe the District Council elections, Lai had dinner with them, arranged through Rogers.

Playing Dumb on IPAC

As for de Pulford, Lai testified he only met him once in Hong Kong in November 2019—at that dinner—and described him merely as Lord Alton's assistant. Lai claimed he never knew de Pulford was executive director of IPAC, and insisted that before the trial he'd never even heard of IPAC.

Lai said de Pulford only contacted him to publish articles in Apple Daily. He testified he never read de Pulford's articles, yet somehow knew de Pulford "was doing good for Hong Kong...working hard to speak well of Hong Kong."

The court rejected that testimony outright. The evidence showed extensive message exchanges between Lai, de Pulford, and Rogers, plus numerous Twitter posts and Apple Daily reports mentioning IPAC—making Lai's professed ignorance "laughable and not credible." The documentary record showed Lai knew exactly who these people were and what they did.

Regarding former Hong Kong Governor Chris Patten, Lai said Patten called himself Lai's friend, but Lai didn't consider Patten his friend. Lai testified that while Patten served as Governor, they rarely met.

After the handover, whenever Patten visited Hong Kong, Lai met with him again—but they had no direct contact, communicating instead through Rogers or Anson Chan. After the National Security Law took effect, Patten had appeared as a guest on Lai's online livestream interview program.

The Taiwan Arrangement

The judgment detailed Lai's "Taiwan line," including connections to Tsai Ing-wen and her aide Chiang Chun-nan. Lai testified he first met Tsai at a banquet hosted by the US Consulate in Taiwan, around the time he founded Taiwan Apple Daily. After Tsai became Taiwan's leader, he met her again—meetings arranged through Chiang.

As for what they discussed, Lai said "sometimes it was about Taiwan policy," but claimed he couldn't clearly remember why he wanted to meet her initially. Lai testified that Tsai was "interested" in him because of his media connections. However, in court Lai didn't mention discussing US policy with Tsai or the Trump administration's attitudes toward Taiwan. Lai also claimed he was "a permanent resident of Taiwan, but not a citizen."

The intermediary between Lai and Tsai was Chiang Chun-nan. Lai testified that when he first met Chiang, Chiang was a well-known writer and columnist for Taiwan's Next Magazine. During Chen Shui-bian's administration, Chiang served as head of Taiwan's Government Security Office. After Tsai took office, Chiang held no formal position but effectively functioned as one of Tsai's key aides, according to Lai's testimony.

Lai recalled that one day, Chiang asked whether Lai knew anyone who could convey to Tsai the Trump administration's internal attitudes and thinking about Taiwan. Lai then introduced two Americans to Tsai: retired US General Jack Keane and former US Deputy Secretary of Defense Paul Wolfowitz.

Intelligence for Hire

Lai testified he believed Chiang knew about his close links with US think tanks and his support for Trump and the Republican Party—so it was "natural" for Chiang to ask him. Lai said he introduced these two former US military and defense officials to Tsai because he wanted to help Taiwan better understand how to deal with the United States.

But the judgment revealed Lai didn't just arrange for these two Americans to provide "intelligence" to Tsai Ing-wen—he also provided "payments" to Chiang Chun-nan at the same time. The judgment noted that even after Chiang stopped writing for Taiwan Apple Daily, he continued receiving salary payments. According to prosecution materials disclosed during trial, from November 2017 to February 2020, Taiwan Apple Daily paid Chiang approximately NT$5.8 million, and Lai never demanded repayment.

The court held that Lai was trying to ingratiate himself with Chiang so Chiang would facilitate Lai's access to Tsai Ing-wen. The court also viewed this as a "return" for Lai's relationship with Tsai—reflecting Lai's intention to serve the Taiwan authorities. Lai testified in response that "he had big business there (in Taiwan)," and even claimed he was a beneficiary of the Taiwan authorities.

Law ABC

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Conspiracy to publish seditious publications. Conspiracy to collude with foreign forces – twice. Those are the charges that just landed Jimmy Lai, founder of Next Digital, twenty years behind bars, the highest sentence under Hong Kong's National Security Law so far. That makes Lai the first defendant convicted for colluding with foreign forces, and the punishment is the heaviest handed down since the law took effect in 2020.

Article 29 of the National Security Law sets the baseline at three to 10 years for collusion offenses. But for "serious cases," the ceiling shoots up – either life imprisonment or a fixed term of at least 10 years.

To determine whether Lai's actions qualified as a "serious case," the court turned to precedent. The sentencing guidelines from the Court of Final Appeal's ruling in HKSAR v. Lui Sai Yu served as the framework. Judges also examined HKSAR v. Ma Chun-man and adjusted the approach based on the specific circumstances surrounding Lai's offenses.

Status Drives Sentence Higher

The court determined that Lai was the "mastermind" and "driving force" behind the conspiracies. That designation carried weight at sentencing. For the seditious publications charge, judges bumped the starting point from 21 months to 23. For each of the two collusion charges, they added three years to the original 15-year baseline, pushing it to 18 years.

But the court did acknowledge reality. Lai is old – 78 years old, to be exact. Taking account of his health and that he's held in solitary confinement, which makes prison conditions harsher than for typical inmates, judges shaved one month off the seditious publications term and one year off each collusion charge. The final tally: 20 years total.

Consider the comparison to Benny Tai, the legal scholar convicted in the "35+" subversion case. The court labeled Tai the mastermind behind the unauthorized primary election scheme – the organizer who pushed the "10 steps to mutual destruction" plan that amounted to advocating revolution. His starting point was 15 years. Because he pleaded guilty, Tai received a one-third reduction, bringing his sentence to 10 years. That made him the most heavily punished of the 45 defendants convicted in that sprawling case.

No Plea Deal, No Mercy

Lai chose a different path. He didn't plead guilty. That meant no sentence reduction – and judges actually added time. The judgment revealed the court's view: Lai harboured deep resentment toward China for years. Whether before or after the National Security Law took effect, his singular goal was bringing down the Chinese Communist Party, even if it meant sacrificing the interests of Hong Kong people. Today's sentencing remarks emphasized that Lai, as the mastermind, acted with careful planning and premeditation.

The math is brutal. National Security Law convicts don't qualify for the standard one-third remission of sentence. At 78, Lai could remain locked up until he's 98.

Three former Apple Daily senior executives caught up in the same case fared differently. Former editor-in-chief Law Wai Kwong, former executive editor-in-chief Lam Man  Chung, and former lead editorial writer and English edition executive editor Fung Wai Kong each pleaded guilty. They received 10 years each – the same term as Benny Tai.

The reality is, that 10-year term represents the statutory minimum. Judges classified their offenses as "serious" too, but credited their guilty pleas with a one-third reduction. Since they didn't testify or assist prosecutors beyond admitting guilt, that was all the leniency they got.

Four Years of Enforcement History

The Hong Kong National Security Law came into force on June 30, 2020, targeting four main categories of offenses: secession, subversion, terrorism, and collusion with foreign forces – the last being what authorities charged Lai with.

Since the law took effect, Hong Kong has seen several high-profile prosecutions. The first came quickly: Tong Ying-kit's case. On July 1, 2020 – just hours after the law became operational – Tong rode a motorcycle bearing a "Liberate Hong Kong" flag straight into a police cordon in Wan Chai, injuring three officers. He was convicted of inciting secession and committing terrorist activities, drawing a nine-year sentence. The court set 6.5 years as the starting point for incitement and eight years for terrorism, with portions running concurrently.

Then there was the "Returning Valiant" group case, which involved a genuine bomb plot. Members planned to plant explosives at the Kwun Tong and Tuen Mun Magistrates' Courts and in cross-harbour tunnels. The ringleader, Ho Yu-wang, pleaded guilty to conspiracy to commit terrorist activities. Six others admitted to an alternative charge of conspiring to cause explosions likely to endanger life or property. Three landed in detention centres; the remaining three received prison terms ranging from 2.5 to 6 years.

The "Alliance" case is still working its way through the courts. The now-disbanded Hong Kong Alliance in Support of Patriotic Democratic Movements of China faces charges along with its former leaders. Former chair Lee Cheuk-yan, vice-chair Albert Ho Chun-yan, and standing committee member Chow Hang-tung are accused of inciting others to subvert state power. Ho has pleaded guilty and awaits sentencing. The other defendants are fighting the charges.