The Jimmy Lai Chronicle : What the Court was Told (6): A Million-Dollar Plot: Buying Access to Taiwan's Leader

Jimmy Lai, founder of Next Media, got nailed on "conspiracy to collude with foreign forces" and other charges. Here's what the court documents and evidence laid bare: Lai had his fingers deep in Taiwan's political and military machinery for years. We're talking about bankrolling retired US military brass and political heavyweights to visit Taiwan, greasing the wheels for then-Taiwan leader Tsai Ing-wen to decode Trump administration moves on Taiwan policy—all part of a scheme to pump up so-called "US-Taiwan relations."

Monthly TWD 200,000 Payouts

Lai built his media empire in Taiwan back in the early 2000s—Taiwan's Next Magazine, Taiwan's Apple Daily, the whole nine yards. But court records show his Taiwan interests ran way past media operations straight into the political arena. The key player here was Chiang Chun-nam (江春男), a Taiwanese writer and political commentator who worked for both Taiwan's Next Magazine and Taiwan's Apple Daily, keeping tight with Lai the whole time. After Tsai Ing-wen took office as Taiwan leader in 2016, Chiang landed the vice president gig at the General Association of Chinese Culture—basically one of Tsai's "right-hand men."

The judgment spells it out: all of Lai's direct or indirect hookups with Tsai Ing-wen—including setting up multiple meetings between her and former US officials or political operators—went through Chiang. Court documents and an internal Taiwan Apple Daily email dated March 25, 2020, expose the money trail: to keep Chiang Chun-nam in his pocket as the go-between, Lai ordered Taiwan Apple Daily CEO Ip Yut-kin in November 2017 to pay Chiang TWD 209,000 monthly. The stated reason? Chiang was "useful" to Lai or Taiwan Apple Daily somehow, but only Lai knew exactly what that usefulness meant.

Taiwan Apple Daily editor-in-chief Eric Chen discovered in 2019 that those monthly TWD 209,000 payments to Chiang had been rolling for over a year—yet Chiang hadn't written a single article or done any work for Taiwan Apple Daily during that stretch. Chen asked Lai directly whether the monthly payments to Chiang should keep going. Lai's answer: "Continue the payments."

Lai testified that when he learned in 2020 about the monthly payments to Chiang Chun-nam without any reciprocal services, he immediately told subordinates to cut them off, and claimed he never directed subordinates to keep paying Chiang. However, Lai confirmed that Taiwan Apple Daily made monthly payments of TWD 209,000 to Chiang from November 2017 to March 2020—totaling over TWD 5.8 million (roughly HKD 1.44 million).

Through Chiang Chun-nam , Lai scored multiple private sit-downs with Tsai Ing-wen. Lai claimed in court these meetings were "mainly public relations activities," but the court pointed out that related messages show he was actually using them to push a political agenda. In December 2016, Lai sent a WhatsApp message to Chiang that flat-out revealed his take on US-China-Taiwan dynamics. He wrote: "Now is the time to break through China... The US appears to be planning to use Taiwan as leverage to counter China's provocations in North Korea and the South China Sea." He also mentioned "US military forces might relocate from Japan to Taiwan" and declared "China doesn't want war; now is the opportunity."

The judge noted that the content above shows Lai wasn't just commenting on the situation—he was actively pushing for the US to use Taiwan as a strategic tool to box in China. This viewpoint became the theoretical backbone for his subsequent funding and actions.

Bankrolling Former US Military Leaders 

After learning from Chiang that Tsai Ing-wen wanted the inside scoop on Trump administration Taiwan policy, Lai arranged through Chiang for two heavyweight US military figures—former US Army Vice Chief of Staff Jack Keane and former Deputy Secretary of Defense Paul Wolfowitz—to travel to Taiwan as advisors.

In January 2017, Lai sent a message to his personal assistant Mark Simon stating: "I dined with the General (Keane) and Paul (Wolfowitz); they will go to Taipei to execute a project linking with Trump... Must maintain strict confidentiality—any media exposure will completely destroy everything." This shows Lai was running the whole operation from the start.

Lai confirmed in court that the two-year consulting fee for both came to USD 3 million.  The judgment revealed that in July 2018, Lai asked Mark Simon about details of a Canadian remittance for a "special project." Mark Simon replied: "USD 750,000 per person per year for both, plus USD 250,000 gift for Keane, totaling USD 1.75 million, plus travel reimbursements and miscellaneous expenses totaling HKD 14.9 million."（

The court concluded that after learning the payment details, Lai raised no objections, proving he "fully knew and agreed to the payments." In 2019, Lai again approved remitting USD 850,000 to Canada to cover the second year's consulting fees and travel expenses for both. The judge questioned during trial: "Since they were providing consulting services to the Taiwan government, why wasn't the Taiwan government making the payments?" Lai explained that because the two were his friends, he had requested their help and arranged the itinerary, so he made the payments—stressing that Tsai Ing-wen had no idea he was footing the bill.

Beyond the financial records, communications showed Lai personally ran the itinerary arrangements, requiring that after Keane and Wolfowitz visited Taiwan four times annually, they must "stay in Taiwan for at least three days each time, meeting with the president and her team." He stated "I will personally travel to Taiwan at the end of the itinerary to understand the results." These details make it crystal clear—he wasn't some observer but the funder and orchestrator of the whole operation.  

Bolton Meeting and "US Military in Taiwan" 

Lai's "resisting China by leveraging Taiwan" moves didn't stop at funding consultant hires. In January 2017, Lai met with John Bolton, then a senior fellow at the American Enterprise Institute who later became White House National Security Advisor. Lai specifically prepared "confidential" notes for the meeting, sending them to Chiang Chun-nam the day before with instructions to destroy them after reading. The content got straight to the point: "Without US military stationed in Taiwan, Taiwan will fall into turmoil; with US military stationed in Taiwan, it can serve as America's Asia-Pacific strategic leverage, ensuring peace across the strait."

Ten days later, Bolton published an article in US media pushing the line that "the US should increase military sales to Taiwan and again deploy military personnel and assets in Taiwan." The content tracked remarkably close to Lai's memorandum.

Looking at all this evidence together, here's the picture: Lai used connections and cash to bankroll visits by high-level US military officials to Taiwan under the "consultant" label, but the real game was pushing US-Taiwan military-political connections through "diplomatic advice." He personally met with US political operators to sell the "US military stationed in Taiwan" concept, attempting to build a back-channel between Washington and Taipei.

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.