Pro-democracy activist Jimmy Lai once hoped U.S. President Donald Trump could help stop the imposition of a controversial national security law. The law not only took effect but was also used to sentence him to 20 years in prison.

Ahead of an anticipated trip by Trump to Beijing to meet Chinese President Xi Jinping next week, Lai’s son said his family is now hoping that Trump can help secure his father’s release.

Lai, a prominent critic of Beijing, founded a pro-democracy newspaper that was shut down during a crackdown following the city’s massive anti-government protests in 2019.

Observers say the former media mogul’s plight symbolizes a decline in freedoms Beijing promised when the former British colony returned to Chinese rule in 1997. In an interview with The Associated Press, Sebastien Lai said he fears the clock is ticking for his 78-year-old father.

Trump is expected to discuss trade, the Iran war and Taiwan with Xi. But he said he is also planning to bring up Lai, telling conservative radio host Hugh Hewitt, “there’s a little bitterness, I would say, with him and Jimmy Lai.”

The younger Lai, 31, said his family is hopeful that Trump could help his father, adding that it’s easier to resolve than many of the other complex geopolitical issues the leaders will discuss.

He fears his father will die in prison, which would devastate the family and make him a martyr, he said.

“It’s a lose-lose scenario for every single person,” he said.

The U.S. diplomatic efforts

Trump has expressed sympathy for Jimmy Lai.

“I feel so badly,” he told reporters in December after Lai was found guilty of conspiracy to collude with foreign forces and conspiring with others to publish seditious articles. He had raised Lai’s case during his October meeting with Xi.

Mark Clifford, president of the Committee for Freedom in Hong Kong Foundation, which advocates for Lai’s release, said people briefed on the October meeting told him that Xi and his staff “noted” Trump’s remarks without pushing back aggressively. Clifford said that suggested they’re willing to talk.

Clifford added that Trump had instructed U.S. Treasury Secretary Scott Bessent to raise Lai’s release in last June’s trade talks with China, according to his source. Bessent again mentioned Trump’s desire to free Lai in a recent meeting with Chinese representatives, who acknowledged it without much comment, Clifford said, citing someone with direct knowledge.

“It is positive that senior Chinese officials have stopped pushing back on the issue,” he said. The Treasury Department did not respond to a request for comment.

In public, though, Beijing has remained tough on Lai. In March, Chinese Foreign Ministry spokesperson Guo Jiakun called him the mastermind behind the riots that shook the city in 2019.

On Thursday, the spokesperson’s office of the ministry didn’t directly answer a question about whether China would consider releasing Lai, saying that Hong Kong issues are internal affairs and foreign interference is not allowed.

The Hong Kong government earlier said Lai’s case had nothing to do with press freedom. In a reply to the AP, it said Lai was convicted after an open and fair trial, and the government will ensure laws are observed and strictly enforced.

The White House did not respond to questions about how vigorously Trump would press for Lai’s release.

Over 100 U.S. lawmakers in a bipartisan group sent a letter to the White House Thursday urging Trump to seek Lai’s release at the upcoming summit with Xi.

Getting prisoners out has become harder

Even as U.S.-China tensions have risen, diplomacy has managed to win the release of some prisoners. In 2024, U.S. pastor David Lin was freed after nearly 20 years in Chinese prison, and Washington and Beijing traded several other prisoners under a diplomatic agreement the same year.

But activists say Beijing is becoming less willing to release prisoners who have confronted it over human rights. The Chinese Nobel laureate Liu Xiaobo died at a hospital in northeast China in 2017 after foreign governments urged China to release him for cancer treatment abroad.

Human rights lawyer Jared Genser, who previously represented Liu, said a White House official told him that Trump had called Xi and urged Liu’s medical release.

Under Xi’s predecessor, Hu Jintao, China was more focused on economic integration and more sensitive to its international reputation, said Genser, who helped win another activist’s freedom in 2007. Xi’s China emphasizes sovereignty and resisting foreign interference, he said.

“China knows that by taking a very tough and unrelenting position that most countries in the world are not going to be willing to do more than privately raise a case,” he said. “That self-censorship to me is the biggest factor … in our inability to secure the release of political prisoners under Xi Jinping, as compared to Hu Jintao.”

It’s not clear how hard U.S. will push for Lai

John Kamm, founder of the Dui Hua Foundation, which advocates for political prisoners, said China previously made concessions when it wanted something, like hosting the Olympics.

But he said U.S. inattention also made it harder to win the release of jailed activists.

“I don’t know of anyone in this administration,” he said, “who cares about political prisoners in China.” An exception might be Secretary of State Marco Rubio, he said, but Rubio’s focus is on other issues.

Kamm said Trump is prioritizing trade, investment and the Iran war. But he said China could agree to release Lai if the U.S. makes concessions on Beijing’s other priorities.

But Thomas Kellogg, executive director of Georgetown Center for Asian Law, said both Beijing and Washington have incentives to make a deal.

Releasing Lai would allow China to signal that it’s ready to move on after almost six years since Beijing imposed the security law in Hong Kong, while Trump’s administration could use a diplomatic win after “a difficult couple of months,” he said.

Kellogg said winning Lai’s release would help the administration earn praise even from its critics.

“If the Trump administration is pushing very hard for Jimmy Lai’s release, then we could get a positive outcome,” he said.

But Wilson Chan, co-founder of the think tank Pagoda Institute, believes the chance for a diplomatic solution is slim as Beijing has a message to send through Lai’s case.

Chan said if the international community keeps raising Lai’s case, Beijing may see him as an influential figure who still poses national security threats. But if they don’t, then Beijing won’t face pressure to act.

Lai’s family fears he will die in prison

Lai, a British citizen, has decided not to appeal his conviction and sentence. The government, which insists Lai is Chinese, is seeking to confiscate his assets on national security grounds.

Sebastien Lai called the move another example of his father “still being attacked.”

The older Lai suffered from health issues including heart palpitations and diabetes, his Hong Kong legal team said in January. The prosecution said a medical report noted his general health condition remained stable. The government insists he was placed in solitary confinement at his own request.

The younger Lai, based in London, has maintained contact with his father through letters during the latter’s over five years in custody. He believes his father will want to live a quiet life if released early.

“My father will die in prison if he’s not freed,” he said. “The Chinese government would be complicit in killing him.”