Days before winning his second presidential term, Donald Trump made a bold promise: if he returned to the White House, he would free a pugnacious, self-made billionaire from a Hong Kong prison. "100% I'll get him out. He'll be easy to get out," Trump declared in a podcastinterviewin October, radiating his trademark confidence. Nearly ten months later, that tycoon Jimmy Lai – a pro-democracy firebrand and persistent thorn in Beijing's side – remains behind bars. The 77-year-old media mogul has spent more than 1,600 days in a maximum-security prison, much of it in solitary confinement, staring down the possibility of spending the rest of his life there. Lai, the outspoken founder of the now-shuttered Apple Daily – a fiercely pro-democracy tabloid newspaper known for years of blistering broadsides against the Chinese Communist partyuntil its forced closure– has become a symbol of Beijing's sweeping national security crackdown on the once-freewheeling financial hub. In his landmark trial, Lai stands accused of two counts of colluding with foreign forces – a crime punishable by life in prison under the 2020 national security law imposed by Beijing – and a separate sedition charge. He has pleaded not guilty to all charges. On Friday, a Hong Kong court is set to begin hearing closing arguments from both defense and prosecutors after a day's delay due to a major rainstorm. The hearings – which are expected to last multiple days – pave the way for a verdict that will decide Lai's fate – and test Trump's resolve to make good on his pledge while trying to clinch a trade deal with Chinese leader Xi Jinping. Asked about Lai ina Fox News radio interviewon Thursday, Trump appeared less certain about the result, but vowed to do everything he can. "I didn't say 100% I'll save him. I said 100% I'm going to be bringing it up, and I've already brought it up, and I'm going to do everything I can to save him." "You can also understand, President Xi would not be exactly thrilled by doing it," Trump said. "With all of that being said, his name (has) already entered the circle of things that we're talking about, and we'll see what we can do." In Hong Kong, dozens of people lined up outside the courthouse on Friday ahead of the hearing amid a heavy police presence. "I am here to support 'Fei Lo' Lai and let him know that he's not alone," said Pun Tak-bun, 81, calling Lai by his colloquial nickname meaning "fat man." "Apple Daily spoke to Hongkongers from the heart." Pun, carrying a yellow umbrella – the symbolic color of the city's once robust pro-democracy movement – was one of the supporters stopped by police in the past two days for an identity check, as officers ratcheted up security around the court complex. KC Chan, 66, said he showed up because he doesn't have high hopes that US President Trump would be able to get Lai out. "If I don't come here this time, I am worried I won't be able to see him again," he said. In the October interview, Trump responded "100% yes" when asked by podcast host Hugh Hewitt whether he would speak to Xi to get Lai out of the country if he won the election. Then, as president, Trump pledged to raise Lai's case as part of US trade talks with China. "I think talking about Jimmy Lai is a very good idea," he told Hewitt in a subsequentradio interviewin May, just days before officials met in Geneva for the first round of talks. "We'll put it down, and we'll put it down as part of the negotiation." Two people who are close to Lai and have been campaigning for his release said they were told that US officials did bring up Lai's case with their Chinese counterparts during the talks. "We understand it was informally brought up at trade talks, but we don't know the context of it," said Lai's top aide Mark Simon, referring to the negotiations in Geneva. Mark Clifford, president of the Washington-based Committee for Freedom in Hong Kong Foundation, said that before trade negotiators met again in London in June, US Treasury Secretary Scott Bessent "had it as a mission" from Trump to ensure that Lai's release was part of the talks. "I'm told that Bessent was tasked by the President and made it as part of his mission," said Clifford, who has been lobbying the US Congress for Lai's release. "Going into those talks, like immediately before those talks, Bessent told people that he was tasked by Trump with getting Jimmy out." CNN has reached out to the Treasury Department for comment. Responding to CNN's request for comment, White House Deputy Press Secretary Anna Kelly said: "As President Trump said, Jimmy Lai should be released, and he wants to see that happen." China's Foreign Affairs Ministry and Commerce Ministry did not respond to requests for comment. Liu Pengyu, a spokesperson for the Chinese Embassy in Washington, said he was not aware of the "specific details" when asked about whether Lai's case was brought up in the trade talks. "We strongly oppose external forces using judicial cases as a pretext to interfere in China's internal affairs or to smear and undermine Hong Kong's rule of law," Liu added. The Hong Kong government has also stood firm, urging "any external forces" – without mentioning the US or Trump – to immediately stop interfering in the city's internal affairs and judicial process. "Any attempt by any country, organization, or individual to interfere with the judicial proceedings in the Hong Kong Special Administrative Region by means of political power, thereby resulting in a defendant not being able to have a fair trial that one should receive, is a reprehensible act undermining the rule of law of Hong Kong and should be condemned," the city's Security Bureau said in a statement. Lai's Friday court hearing comes just days after Trump extended a trade truce with China, giving both sides another 90 days to try to settle their trade and tech disputes. In recent weeks, Trump has eased his confrontational stance toward Beijing, and has spoken enthusiastically about visiting China at Xi's invitation in the "not too distant future" if a deal is reached. As part of that push, he has rolled back certain export controls on China – includingreversing a banon sales of Nvidia's H20 chips. This week, heopened the doorto sending China more advanced AI chips. Experts on US-China relations say it remains unclear whether Trump can deliver on his pledge to free Lai, a China-born British national, citing his transactional style and unpredictable policy shifts. "Jimmy Lai is British, not American. Given the high profile of his case, I doubt that China will be willing to make a deal," said Yun Sun, director of the China program at the Stimson Center think tank in Washington. "But the trade talks are higher priority for Beijing. If Trump prioritizes Jimmy Lai's release, Beijing will be able to negotiate although it all depends on the terms." Jean-Pierre Cabestan, a senior researcher at the Asia Centre think tank in Paris, said the uncertainty cuts both ways. "How much pressure Trump will put on Xi to reach such a deal? Hard to say because the US administration has so many other priorities ahead of Jimmy Lai," he said. "But the big question is whether Xi will accept such a quid pro quo?" But Lai's family and supporters remain hopeful. "We're incredibly grateful that the president knows about my father's case and has said that he will free him," said Sebastien Lai, Jimmy Lai's son. "The president has a tremendous track record in freeing prisoners around the world. So hearing this gives our family a lot of hope." Others note the willingness of Trump administration officials to discussing Lai's case, as well as his broad backing in Washington and within the Catholic community. "I know people in the Trump administration. We talk about it. They bring it up. The Catholic community has reached out to the White House and made their voice known. Various senators have reached out," said Simon, the Lai aide. Lai's fortunes, both personal and financial, are inextricably tied to the transformation of Hong Kong. Born in mainland China, he arrived in the British-ruled city in the bottom of a fishing boat at age 12 and dirt poor. He worked his way up the factory floor of a textile company to become a clothing tycoon – a rags-to-riches story that echoed Hong Kong's own rise as a bustling commercial hub. But China's deadly 1989 crackdown on student protesters in Tiananmen Square politicized Lai and created something of a rarity in Hong Kong: a wealthy tycoon willing to openly criticize Beijing's leaders. He moved out of the clothing business and chose a new role – media baron. Lai founded Apple Daily in 1995, two years before Hong Kong was handed over to China. The outspoken publisher and his newspaper were at the forefront of the city's pro-democracy movement. A known vocal supporter of Trump and a devout Catholic, Lai traveled to Washington at the height of the 2019 protests, where he met withthen Vice President Mike Penceand other USpoliticiansto discuss the political situation in the city. The media mogul had long held a conviction that Trump and the US government should not shy away from supporting Hong Kong's civil liberties, which are key for the city's status as a conduit between China and international markets. "Mr. President, you're the only one who can save us," Lai said in aninterview with CNN in 2020weeks before he was arrested. "If you save us, you can stop China's aggressions. You can also save the world." Prosecutors have argued that Lai's actions amounted to lobbying for sanctions against Beijing and Hong Kong, an act prohibited under the national security law that was imposed following 2019's huge and sometimes violent pro-democracy protests and has transformed the city. Lai's lawyers have countered that Lai had stopped those acts after the national security law came into effect on June 30, 2020. Taking the stand in his own defense in November, Lai said he had never spoken with Trump. "I don't think he knew me. I think his aides knew me and briefed him about me," he said. In Washington, efforts to call for Lai's release have continued through Joe Biden's presidency and into Trump's second term. In March, a bipartisan group of US House representativesintroduceda bill to rename the street in front of the Hong Kong Economic and Trade Office in Washington as "1 Jimmy Lai Way." That same month, US Secretary of State Marco Rubio – a former top China hawk in the Senate – said inan interviewthat getting Lai out of jail was a "priority." "We've raised it in every possible form and they know that it's important to us," Rubio said, referring to Chinese officials. "It's not something we've forgotten about and that it remains a priority, and I think other countries around the world are making the same point as well to the Chinese." British Prime Minister Keir Starmer brought up the case of Lai in his first meeting with Xi, on the sidelines of the G20 summit in Brazil in November 2024. British Foreign Secretary David Lammy has also urged Lai's release,callinghis imprisonment "cruel and unusual punishment" anddescribingthe case as "a priority for the UK government" — remarks that drewa sharp rebukefrom Beijing. So far all of Hong Kong's national security trials have been heard by a panel of specially selected judges, not juries – a departure from the city's common law tradition. The closing arguments are expected to take multiple days and it could be weeks, or even months, before the judges render their verdict. People campaigning for Lai's release argue that given his old age and frail health, it'll be more trouble for Beijing and Hong Kong authorities to keep him in prison than set him free. "If he dies in prison, he's going to be trouble forever. He'll be a martyr. He'll be a symbol of resistance. He'll be a symbol of the cruelty of the Chinese Communist regime. And why would (Beijing) want that?" said Clifford, who wrote a biography of Lai titled "The Troublemaker." Simon, the top aide, said Lai has to be convicted first, before things can start moving forward to get him out of prison. While Washington has used diplomacy to secure the release of political prisoners in mainland China in the past, such interventions would be rare — if not unprecedented — in Hong Kong, which has its own separate legal system, experts say. Paul Harris, former chairman of Hong Kong's Bar Association, said the fact that Lai is in Hong Kong does not create an obstacle to his release. Under Hong Kong's mini-constitution, the Basic Law, the chief executive has the power – and the duty – in appropriate cases to pardon convicted prisoners or commute their sentences, he explained. "So that power is there, and it's a matter for the Chief Executive's decision whether he wants to use it, and one can safely assume that if the President of China wants him to use it, he will use it," Harris said, referencing Xi. "Jimmy Lai is in the second half of his 70s. He has certain health problems. It is totally consistent with the rule of law, as it has always operated, to release elderly prisoners with health problems. And so if the will is there, it can be done." But for supporters of Lai, the campaign to free him is a race against time. Sebastien Lai said he's deeply concerned about his father's deteriorating health. "He's 77 this year, turning 78 at the end of the year, any type of incarceration is incredibly worrying for his health, never mind the solitary confinement and the diabetes," he said, calling his father's prolonged solitary confinement "a form of torture." "And during the summer, Hong Kong goes up to 30, almost 40 degrees, and he's in a little concrete cell, so he bakes in there. We're incredibly worried about him." The Hong Kong government said it strongly condemns what it calls "misleading statements" about the treatment of Jimmy Lai in custody. "The remarks by Sebastien Lai regarding Lai Chee-ying's solitary confinement are completely fact-twisting, reflecting a malicious intention to smear and attack the HKSAR Government," it said in a statement, adding Lai had requested his removal from general prison population. Sebastien Lai said his concern for his father is also layered with pride. "I'm very proud that someone like my father has decided to do what he did – campaigning for democracy for the last 30 years, staying in Hong Kong when it mattered, when the national security law was coming down…and almost acting like a lightning rod." "On a personal level, it's devastating. But on a grander, historical level, it's important to keep watch." CNN's Manveena Suri and Alejandra Jaramillo contributed reporting. For more CNN news and newsletters create an account atCNN.com
