The Jimmy Lai Chronicle – What the Court was Told (2): The Money Trail Behind Jimmy Lai's Washington Machine

Jimmy Lai's conviction on collusion charges rests on an 855-page verdict that reads like a roadmap of foreign interference. The court dedicated an entire chapter to dissecting Lai's foreign connections, with the "US front" taking center stage. This isn't speculation—it's documented in WhatsApp messages, emails, and wire transfers. At the heart of it all: Mark Simon, Lai's assistant, described by judges as a "mystery man" who functioned as Lai's eyes, ears, and fixer in Washington's corridors of power.

The Presidential Pipeline

On the US front, the verdict traces connections straight to the top. Lai admitted he never met Trump but knew Trump had name-dropped him at a campaign rally. The real action, according to court documents, centered on Vice President Mike Pence.

Lai met Pence in Washington in July 2019, then again in October after one of Pence's speeches. Lai claimed his original purpose was simply “to relay to him what happened in Hong Kong”. Mark Simon arranged meetings through Christian Whiton, a senior State Department advisor. Then came word: Pence wanted to see him. Lai's story? He didn't dare make specific requests to the Vice President of the United States.

During the same trip, Lai sat down privately with Secretary of State Mike Pompeo in his office. He denied requesting Pompeo to do anything, just asked him  to “speak up for Hong Kong and support Hong Kong”. The pattern would repeat itself throughout the verdict: meetings with top officials, followed by claims of innocent conversation.

But here's where the story gets interesting. After the Hong Kong National Security Law took effect in July 2020, Lai went to extraordinary lengths to get back to the US and meet Pence again.

Desperate Measures

In February 2020, Lai wrote an op-ed for The Wall Street Journal titled "China’s Facade of Stability". Mark Simon soon informed him that Pence and his senior aides were paying attention. At the time, Lai faced travel restrictions from a criminal intimidation case. His workaround? Using the birth of his granddaughter to process exit procedures—what Lai called "very good security." He told Mark Simon he could arrive in the US by June 20, expressing his desire to see the "big boss." Lai later denied this meant Trump, claiming he meant Pence.

Lai planned to meet US government officials, including Pence, between July 4-11, 2020. The court denied his exit application. On June 13, Mark Simon reported that US officials and journalist friends were "disappointed" Lai couldn't make it.

The court wasn't buying it. Judges found that Lai knew full well the National Security Law was about to be enacted but still schemed to visit the US in July 2020—proof of his "unwavering commitment to international lobbying." More damning: Lai deliberately concealed his planned meetings with US officials in his bail application. During trial, he changed his testimony, admitting he hid the meetings because they were "too politically sensitive" and disclosure would tank his chances of getting approval.

The verdict's language is blunt: Lai was "evasive and contradictory," knowingly arranging to meet officials as the National Security Law loomed, hoping to prevent its implementation through lobbying that would interfere with foreign policy—all while "deliberately deceiving and misleading the court."

The Taiwan Card

Lai maintained tight connections with then-National Security Advisor John Bolton, particularly on Taiwan matters. The relationship began at a Washington think tank conference in 2018. After that, Lai met Bolton on every US visit, and Bolton met with Lai whenever he visited Taiwan. Bolton visited Taiwan frequently in 2018 and 2019, though Lai claimed they just "chatted casually."

The evidence tells a different story. When Lai met Bolton in January 2017, they discussed US military presence in Taiwan and prepared a "top secret" memorandum. Bolton then published an article titled "Revisiting the 'One China Policy': Strengthening US-Taiwan Military Relations Helps Counter Beijing's Provocations"—content strikingly similar to their confidential memo.

The Insider's Playbook

The verdict also spotlights Mary Kissel, assistant to Secretary of State Pompeo. Lai said he'd known her since 2009 as a "personal friend." After leaving Hong Kong, she worked as an editorial writer for The Wall Street Journal before becoming Pompeo's assistant. Before Lai met Pompeo in July 2019, Mark Simon relayed two requests from Kissel.

First: Follow protocol strictly—handshakes and polite greetings only, no hugging, because she wanted to stay professional and not reveal their friendship.

Second: Be as specific as possible presenting Hong Kong issues to Pompeo, including "sanctioning the children of Hong Kong and CCP leaders who suppress protesters" and elevating Hong Kong and Taiwan to a status similar to Berlin during the Cold War.  But the topics about "protecting Hong Kong protesters" and maintaining the unique US-Hong Kong trade relationship were considered highly sensitive by all parties.

In other words, Kissel provided a strategic roadmap for lobbying US officials and targeting central and SAR government officials for sanctions. Yet Lai claimed he never communicated directly with Kissel—only through Mark Simon.

The Hired Guns

Christian Whiton, senior State Department advisor, entered the picture in 2019 through Mark Simon. Lai hired Whiton as a consultant to introduce him to US senators, representatives, and government officials—paying "consulting fees." Whiton had served as a senior White House aide for years and had extensive connections. He facilitated introductions for Lai during trips in July 2019 and subsequent visits. Lai told the court that when he traveled to Washington in July and October 2019, Whiton was no longer working at the White House.

Then there's Rupert Hammond-Chambers, president of the US-Taiwan Business Council. Lai claimed not to remember his name, but evidence showed it appeared in Lai's emails. Lai later mentioned someone called "Rupert" who worked with former US Army General Jack Keane and former Deputy Defense Secretary Paul Wolfowitz at a Taiwan consulting company. Because he was a "Taiwan affairs expert," Lai made payments to him.

The Pentagon Connection

The verdict identifies two former US military officials in Lai's network. Jack Keane, former US Army Vice Chief of Staff, national security analyst, and chairman of the Institute for the Study of War, was offered positions as Defense Secretary or Army Secretary after Trump's election but he declined. Lai knew Keane had close White House ties and paid him fees to obtain advice on the US government's stance on Taiwan.

Between 2013-2014, Lai hired Paul Wolfowitz as his consultant in Myanmar, claiming he was looking for investment opportunities. Lai also paid Wolfowitz Taiwan consulting fees because he knew Wolfowitz had extensive experience handling Asian policy. Lai met him separately in Washington in 2016, January 2017, and May 2017, then again in Paris in 2017 and Taipei in December 2017.

Apart from the two former military officials, Lai introduced former US Consul General to Hong Kong and Macau James Cunningham to Taiwan leader Tsai Ing-wen. The three met in March 2018, with Cunningham explaining to Tsai what he could do in Washington. Lai paid Cunningham's travel expenses to Taiwan.

Orchestrating the Opposition

The verdict details how Lai facilitated US lobbying trips for pan-democratic figures through Cunningham, including former Chief Secretary Anson Chan's March 2019 visit and Martin Lee's May trip with other pan-democrats. Cunningham volunteered to help, but Lai made the payments.

In March 2019, Lai sent photos of Anson Chan meeting Pence via WhatsApp to Apple Daily executives Cheung Kim-hung and Chan Pui-man, instructing them to give the news prominent coverage. Regarding Martin Lee's US visit, on March 26, 2019, Lai sent Martin Lee a WhatsApp message explaining he wanted Cunningham to participate in assisting pan-democrats with US lobbying because the US Congress was controlled by Democrats and Cunningham was a Democrat. However, Lai denied that sanctioning the Hong Kong government and officials was part of the pan-democrats' May US visit agenda.

But on March 27, 2019, Lai told Mark Simon that given potential turbulence in Hong Kong-China relations over the next two years, they should retain Cunningham in Washington to handle lobbying work regarding Hong Kong. Lai even suggested Cunningham propose anti-extradition legislation in the US Senate or House. The verdict found that while Lai denied making payments to Cunningham, the court determined Lai instructed Mark Simon to pay Cunningham and lied to Martin Lee so Cunningham could assist Lee in influencing US foreign policy toward China.

The Extended Network

The verdict also mentions Next Digital independent non-executive director and "Live Chat" co-host Mark Clifford, former Israeli Deputy Prime Minister Natan Sharansky, American sinologist Perry Link, and former American Institute in Taiwan chairman Raymond Burghardt as part of Lai's "US network."

Lai had known Clifford for 20-30 years, noting he had long served as a senior correspondent for US media in Hong Kong and once served as editor-in-chief of the South China Morning Post. As for former Israeli Deputy Prime Minister Natan Sharansky, Lai said he'd known him since before the 2014 "Occupy Central" movement, then met in Jerusalem, and saw him again in 2020 on an online live program. Perry Link, who also appeared as a guest on Lai's live program, Lai said he'd known for about 30 years—a renowned scholar and his son's godfather.

Regarding former American Institute in Taiwan chairman Raymond Burghardt, Lai said he met him when Burghardt served as the de facto US representative to Taiwan, meeting him several years after founding Apple Daily. Lai said he was familiar with Taiwan, Vietnam, and China, and had also worked at the Beijing consulate when young.

Capitol Hill Access

Lai maintained contact with US congressmen, including then-House Speaker Nancy Pelosi, whom he met through Martin Lee's introduction. Lai said the two were friends for many years. The three met in October 2019.

Lai also met with several US senators between September and October 2019. Regarding Rick Scott and Ted Cruz, Lai said when he was in Washington in July 2019, Whiton arranged for them to meet. When the two came to Hong Kong in September and October 2019, they met again—they had come to Hong Kong to "observe" the anti-extradition protests.

As for Bill McGurn, Lai said they met in Hong Kong years ago and were close friends, both Catholics. When Lai converted to Catholicism, McGurn was his godfather. McGurn was also a writer for The Wall Street Journal.

Notably, the verdict also mentions Lai admitted donating to US think tanks, between $20,000-$50,000 annually, because he agreed with the think tanks' ideals. However, he emphasized the donations had no strings attached and he had no intention of influencing US policy toward the central or SAR governments.

The Man Behind the Curtain

Mark Simon, Lai's assistant described in the verdict as a "mystery man," played a pivotal role in Lai's "US network." Though Mark Simon held no official position at Next Media, Lai deeply trusted him, entrusting multiple companies and funds under his banner to Mark Simon's full control. While Lai claimed he rarely discussed politics with Mark Simon and believed he had no US government connections, the judge found Lai's testimony incredible because the court believed Mark Simon had close ties with the US government and the National Security Council (NSC)—Lai was deliberately evasive. Most importantly, Mark Simon appeared actively involved in discussions about targeting Hong Kong officials for sanctions.

The verdict mentions that on April 24, 2020, Lai, Whiton, Keane and Mark Simon engaged in email discussions about the "Magnitsky Act," during which Mark Simon responded to Wolfowitz's questions involving sanctions against Chinese officials and companies. Later that day, Keane suggested WhatsApp communications might be compromised and recommended using Signal.

The Sanctions List

The verdict also mentions Mark Simon provided the National Security Council with a list of Hong Kong officials to be sanctioned. Mark Simon left Hong Kong on April 18, 2020, about two months before the National Security Law took effect. On May 4, 2020, Mark Simon informed Lai that then-Deputy National Security Advisor Matthew Pottinger requested that Apple Daily reprint his speech directly attacking China.

The court found that communications between Lai and Mark Simon indicated Lai knew Mark Simon had clear connections with the National Security Council (NSC) and the US government. There was clearly a "division of responsibilities" between the two—Mark Simon handled lobbying in the US while Lai continued his work in Hong Kong.

On May 29, 2020, Mark Simon created a WhatsApp group called "DC Dems" including Lai, himself, Cunningham, and Wolfowitz. Communications within this group continued until June 6, 2020. On May 30, 2020, Mark Simon stated he had just spoken by phone with a "Capitol Hill" group and briefed the group on sanctions against senior officials handling Hong Kong affairs. The court found this showed Lai agreed with US government "punitive" actions against China.

The verdict also found that when Mark Simon contacted and communicated with NSC personnel, he was acting on Lai's behalf, demonstrating Mark Simon's role as an "intermediary," conveying his US connections to Lai. The verdict determined Mark Simon played a central role in facilitating Lai's cooperation with external forces, traceable back to the establishment of the Taiwan consulting company in 2017 and continuing until after the National Security Law was enacted.

The Verdict

Based on all evidence, the court was convinced that even after the National Security Law took effect, Lai continued seeking international support through communication and cooperation with overseas contacts, advocating sanctions, implementing technology embargoes, revoking Hong Kong's special status, and more. Since March 2019, Lai maintained close overseas relationships to prevent the amendment of the Fugitive Offenders Ordinance, intending to lobby the US to oppose it and mobilize the international community against the Chinese and Hong Kong SAR governments, using Apple Daily as a platform to mobilize Hong Kong people to take to the streets to protest the amendment.

The court found that under the guise of fighting for freedom and democracy, Lai cooperated with his foreign network and repeatedly requested foreign countries, especially the US, to impose sanctions, blockades, or engage in other hostile activities against the central or SAR governments.

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.