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

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

Blog

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

2026-01-22 10:02 Last Updated At:10:02

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

** The blog article is the sole responsibility of the author and does not represent the position of our company. **

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.

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