Jimmy Lai Case Explained: Press Freedom, Politics and the Trump-Xi Summit Focus

• Trump says he may discuss Jimmy Lai’s imprisonment with Xi Jinping

• Lai, founder of Apple Daily, is serving a 20-year sentence in Hong Kong

• His case has triggered global concern over press freedom in Hong Kong

The much-awaited and closely watched diplomatic engagement this week will see US President Donald Trump meet Chinese President Xi Jinping in Beijing from May 13 to 15, marking the first visit by a sitting American president to China in nearly a decade.

The high-stakes summit is expected to focus on some of the most sensitive issues in US-China relations, with the case of jailed Hong Kong media tycoon Jimmy Lai emerging as a key talking point, alongside tensions over Taiwan arms sales.

US President Donald Trump said on Monday that he may raise the case of jailed Hong Kong media tycoon Jimmy Lai during his upcoming meeting with Chinese President Xi Jinping, bringing renewed political attention to the long-running case.

Speaking at the White House, Trump suggested he had already discussed the issue previously and could do so again.

“I bring up Jimmy Lai… it might be a hard one for me,” Trump told reporters, adding, “Jimmy Lai he caused lots of turmoil for China. He tried to do the right thing, wasn’t successful, went to jail, and people would like him out. And I’d like to see him get out too.”

He also compared the situation to other legal cases, saying: “It’s like saying to me, if Comey ever went to jail… he’s a dirty cop. But Jimmy Lai isn’t that way.”

Who is Jimmy Lai?

Jimmy Lai was born in Guangzhou in southern China into a wealthy family that lost its fortune after the communist takeover in 1949. At just 12 years old, he fled his village and arrived in Hong Kong as a stowaway on a fishing boat, marking the beginning of a dramatic personal journey.

Starting from humble beginnings, Lai worked odd jobs in Hong Kong, including in a small clothing shop where he taught himself English. He gradually built a successful business career, eventually founding a multi-million-dollar fashion empire, including the popular international brand Giordano.

His path took a major turn after the 1989 Tiananmen Square crackdown in Beijing, when he became an outspoken critic of China’s leadership and a supporter of pro-democracy movements. He began writing critical columns and later entered the media industry, establishing publishing ventures that grew into some of Hong Kong’s most influential outlets, including the widely read Apple Daily and Next Digital.

As tensions with Beijing escalated, Lai sold his mainland business interests and focused on media and activism, with his publications becoming strong voices for press freedom and democracy.

In 2021, amid growing pressure from authorities, Lai even appealed to then US President Donald Trump for support, calling him “the only one who can save us” from China.

His rise from refugee to media tycoon and outspoken democracy advocate has made him one of the most prominent—and controversial—figures in Hong Kong’s recent political history.

Why Lai Is In Jail?

Lai was arrested after Beijing introduced a sweeping national security law in 2020 following mass anti-government protests in 2019. Authorities accused him of collusion with foreign forces and publishing seditious content through Apple Daily.

The newspaper was later shut down after police raids, and Lai was sentenced to 20 years in prison in February 2026, along with several former staff members.

According to Reuters, his case has sparked global concern over Hong Kong’s tightening security environment and shrinking press freedoms. Human rights groups and foreign governments have criticised the crackdown.

Will China Shift on Lai Case?

Beijing has taken a firm stance on the case of jailed media tycoon Jimmy Lai, saying he must be “severely punished according to the law” while rejecting criticism from abroad. Chinese authorities have also accused foreign governments of interfering in Hong Kong’s judicial matters.

The position highlights China’s broader response to international concerns over Hong Kong’s legal environment since the 2020 national security law. Beijing has consistently described external criticism as unwarranted interference, making diplomatic efforts to influence Lai’s case increasingly difficult.

Observers, including those cited by The Associated Press, say Lai’s case reflects broader concerns about freedoms promised to Hong Kong after the 1997 handover. His family has also warned about his age and declining health in prison.