The Jimmy Lai Chronicle – What the Court was Told (3): How the Game with America's Top Brass is Rigged

Next Magazine founder Jimmy Lai just got nailed on three counts: conspiracy to publish seditious material and conspiracy to collude with foreign forces. Here's what the 855-page court judgment lays bare—Lai wasn't just schmoozing with public figures like then-VP Mike Pence or Secretary of State Mike Pompeo, he bankrolled two retired US military heavyweights to work Taiwan's leadership and tilt Washington's China policy.

Starting in 2017, Lai paid hefty consulting fees to retired US General Jack Keane and former Deputy Secretary of Defense Paul Wolfowitz to advise Taiwan's Tsai Ing-wen and help her decode White House thinking on Taiwan. Court records show Lai knew exactly what he was buying—direct influence over US policy machinery through men who had the President's ear.

The judgment traces how Lai cultivated these contacts and why. Both Keane and Wolfowitz wielded serious clout in Pentagon and White House circles. Lai maintained ties with them for years, fully aware they could shape US military and diplomatic strategy.

Trump's Go-To General

Court documents show Lai knew Keane was a four-star general dripping with medals. They met at a friend's gathering—Lai couldn't pin down exactly when. Keane's resume stacks up: Vice Chief of Staff of the US Army, national security analyst, president of the Institute for the Study of War. On November 17, 2016, Lai messaged his assistant Mark Simon via WhatsApp that Trump had offered Keane either Secretary of Defense or Secretary of the Army after the election. Keane turned it down. That detail matters—it shows Trump trusted Keane enough to hand him cabinet-level power.

In 2017, Lai messaged Chiang Chun-nan, an aide to Tsai Ing-wen, saying Keane had become Trump's personal advisor and that he believed Keane could influence the President's thinking.

By September 6, 2018, Mark Simon told Lai that Keane was again being floated for Secretary of Defense. Simon's assessment: "Congress, people inside the government, and the President himself all respect Keane." Lai testified he knew Keane had tight links to the US government.

Keane himself called Lai a good friend. On November 26, 2020, during an online Twitter chat, Keane praised Lai's work in the US and noted Lai got "special treatment to speak with American leaders." Keane said plainly: "I'm a good friend of Jimmy Lai. He's a highly respected person in America, and we have great respect for him." The judgment notes Lai was the only Asian maintaining this kind of unique relationship with American leaders—and that "American leaders recognize him."

The Myanmar Advisor Who Knew Asia

Former Deputy Secretary of Defense Paul Wolfowitz also served as US Ambassador to Indonesia, giving him rich experience in US Asia policy. Lai testified he met Wolfowitz briefly in 2013 and 2014 while hunting for investment opportunities. He later hired Wolfowitz as a Myanmar advisor and paid him consulting fees. From 2016 to 2019, they stayed in contact via WhatsApp, meeting in Washington in 2016, January 2017, and May 2017, then in Paris in 2017 and Taipei in December 2017.

Lai's bank records tell the money story. As early as July 2013, he wired roughly HK$587,000 to Wolfowitz. Between 2014 and 2019, he made five more deposits totaling over HK$1.17 million.

Court Rejects Lai's Money-and-Motive Defense

Because of their top-tier influence in US government circles, Lai hired both former military officials to consult for Tsai Ing-wen.

The judgment rips Lai's testimony as "contradictory, inconsistent, evasive, and unreliable." Lai insisted he never paid anyone to influence US policy toward China or Hong Kong. But the evidence contradicts him—he shelled out tens of millions of dollars to Keane and Wolfowitz to advise Tsai Ing-wen, explicitly advocating for using Taiwan as "leverage" against China. The payments benefited US and Taiwan interests at China's expense.

The judgment defines the "Taiwan consulting" as collaboration between Lai, Mark Simon, White House National Security Advisor John Bolton, Keane, Wolfowitz, former US Consul General to Hong Kong James Cunningham, and Chiang Chun-nan. The goal? Advise Tsai to secure US military presence in Taiwan, using the island as a lever to counter China's influence in Asia.

Though Lai denied it, the court rejected his explanation outright. The judgment states flatly that "promoting increased US military presence in Taiwan and relocating US forces from Japan to Taiwan" was Lai's idea.

According to the judgment, on December 12, 2016, Lai replied to Chiang via WhatsApp: "Now is the time for a breakthrough with China. The US should use Taiwan as a bargaining chip against China's 'aggressive behavior' in the 'South China Sea and Korea' and relocate US forces from Japan to Taiwan."

On January 5, 2017, Lai messaged Chiang about his Washington dinner with Keane and Wolfowitz. He told Chiang that Keane had become Trump's personal advisor and was willing to help. On January 19 of the same year, the mission was confirmed in Taipei. Keane told Chiang he needed to meet Tsai before her trip abroad and required a 15-minute private conversation with her.

Meanwhile, Lai and Mark Simon applied to the US Department of Justice for approval for Keane and Wolfowitz to provide consulting services to Tsai. Approval came through in June 2017, and Mark Simon arranged for Tsai, Keane, and Wolfowitz to meet in Taiwan on August 16, 2017.

Hire Retired Generals to Whip Taiwan's Military Into Shape

After the meeting, Lai personally contacted Keane and Wolfowitz to get their read on the session with Tsai.

On August 19—three days after Keane and Wolfowitz met Tsai—Lai personally relayed their thoughts to Chiang Chun-nan via WhatsApp for Chiang to pass to his "boss" Tsai Ing-wen. Lai's message: "Given that Taiwan is back in the international spotlight, signing long-term energy contracts will help attract Washington's attention, which will promote sustained communication between both sides. Recruit retired US generals to enhance Taiwan's military thinking, and use this as a foundation to comprehensively improve Taiwan's military capabilities. Finally, hire a top diplomat to establish and maintain close ties with Taiwan at the diplomatic level in Washington."

Lai also mentioned a ten-year contract in the message and suggested Taiwan hire retired generals to train the military and equip it with modern technology. The message also referenced hiring "a top diplomat"—that was former US Consul General to Hong Kong James Cunningham.

Lai then sent Cunningham's information to Chiang, "because Taiwan needs someone in Washington to help handle relations with the US government." Lai believed Taiwan's own personnel were inefficient in dealing with the US government, and he thought Cunningham could help Taiwan improve the efficiency of its diplomatic channels.

Tsai's meeting with Cunningham was eventually arranged for March 15, 2018, and Lai attended at Tsai's request. Lai admitted during testimony that after meeting Tsai in late March 2018, he was eager for Taiwan to engage with Cunningham to rebuild Taiwan's diplomatic channels with the United States.

The judgment also states that in May 2018, Lai relayed the views of Keane and Wolfowitz to Chiang in a WhatsApp message, arguing that the Trump administration at the time was the best opportunity for Taiwan to deepen its diplomatic relationship with the United States.

The pattern is clear. Lai's collusion with former senior US military officials served a dual purpose: exploit these "good friends'" influence over the White House, the military, and even the President himself to tilt US’s China policy, while positioning them as a bridge between Taiwan and the United States. In doing so, Lai achieved his goal of using Taiwan as a bargaining chip to "counter China."

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.