He was 12 when he fled his village in mainland China, arriving in Hong Kong as a stowaway on a fishing boat.
Like a number of the city’s famous tycoons, he went from a subordinate role, working in a sweatshop in Hong Kong, to founding a multi-million dollar empire.
But unlike others who have reached the top, Jimmy Lai has also become one of the fiercest critics of the Chinese state and a leading figure in Hong Kong’s pro-democracy movement.
His arrest on Monday is the most publicized use of the national security law imposed on the territory by Beijing in June.
From rags to wealth
He was born in Guangzhou, a city in southern China, to a wealthy family who lost everything when the Communists took power in 1949.
After working odd jobs and knitting in a small clothing store, he learned English on his own, before founding the international clothing brand Giordano.
The channel was a huge success. But when in 1989 China sent tanks to crush pro-democracy protests in Beijing’s Tiananmen Square, Mr. Lai began a new journey as a democracy activist and as an entrepreneur.
He started writing articles criticizing the massacre that followed the Beijing protests and established a publishing house that has grown to become one of Hong Kong’s most influential.
As China responded by threatening to close its stores on the mainland, which caused it to sell the company, Mr Lai launched a series of popular pro-democracy titles, which now include Next, a digital magazine and the Apple Daily newspaper.
In an increasingly fearful local media landscape for Beijing, Lai is a lingering thorn for China both through her publications and her writings that openly criticize the Chinese leadership.
It saw him become a hero to many Hong Kong residents. Mr. Lai is a rare rebel tycoon who dares to stand up to Beijing. But on the mainland, he is seen as a “traitor” who threatens Chinese national security.
In recent years, masked assailants have bombed Mr. Lai’s home and the company’s headquarters. The 71-year-old was also the target of an assassination plot.
But none of this prevented him from expressing his views vigorously. He has played an important role in the city’s pro-democracy protests and has already been arrested twice this year on charges of illegal assembly for previous protests ahead of Monday’s arrest.
“I am a troublemaker. I came here with nothing, the freedom of this place has given me everything, ”he told AFP in an interview in June.
“Maybe it’s time to repay this freedom by fighting for it,” he said.
When China passed Hong Kong’s new national security law in June, Lai told the BBC “it was the death knell” for the territory.
The influential entrepreneur also warned that Hong Kong would become as corrupt as China. Without the rule of law, he said, its coveted status as a global financial center would be “totally destroyed.”
For his admirers, Mr. Lai is a man of courage who has taken great risks to defend Hong Kong’s freedoms.
“I have enormous respect for Mr. Lai. Clearly a courageous man and probably one of the very few who have maintained his business interests without diluting his principles, ”one Twitter user wrote after his arrest.
The media mogul is known for his frankness and flamboyant acts. Earlier this year, he urged US President Donald Trump to help the territory, saying he was “the only one who can save us” from China. His newspaper, Apple Daily, ran a front-page letter that ended: “Mr. President, please help us. “