He was 12 years old 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 famed tycoons, he went from a menial role, toiling in a Hong Kong sweatshop, to founding a multi-million dollar empire.
But unlike others who rose to the top, Jimmy Lai also became 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 highest-profile use of the national security law imposed on the territory by Beijing in June.
Rags to riches
He was born in Guangzhou, a city in southern China, to a wealthy family that lost everything when the communists took power in 1949.
From working odd jobs and knitting in a small clothing shop he taught himself English, eventually founding the international clothing brand Giordano.
The chain was a huge success. But when in 1989 China sent in tanks to crush pro-democracy protests in Beijing’s Tiananmen Square, Mr Lai began a new journey as a vocal democracy activist as well as an entrepreneur.
He started writing columns criticising the massacre that followed the demonstrations in Beijing and established a publishing house that went on to become one of Hong Kong’s most influential.
As China responded by threatening to shut his stores on the mainland, leading him to sell the company, Mr Lai launched a string of popular pro-democracy titles that now include Next, a digital magazine, and the widely read Apple Daily newspaper.
In a local media landscape increasingly fearful of Beijing, Lai is a persistent thorn for China both through his publications and writing that openly criticises the Chinese leadership.
It has seen him become a hero for many residents in Hong Kong. Mr Lai is a rare rebel tycoon who dares to stand up to Beijing. But on the mainland he is viewed as a “traitor” who threatens Chinese national security.
In recent years masked attackers have firebombed Mr Lai’s house and company headquarters. The 71-year-old has also been the target of an assassination plot.
But none of this has stopped him from airing his views robustly. He has been a prominent part of the city’s pro-democracy demonstrations and was already arrested twice this year on illegal assembly charges for earlier protests before Monday’s arrest.
“I’m 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 I paid back for that freedom by fighting for it,” he said.
When China passed Hong Kong’s new national security law in June, Mr Lai told the BBC “it spells 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 hub would be “totally destroyed”.
For his admirers Mr Lai is a man of courage who has taken on great risks to defend the freedoms of Hong Kong.
“I have enormous respect for Mr. Lai. Clearly a man with courage and probably among the very very few who has maintained his business interests without diluting his principles,” wrote one Twitter user after his arrest.
The media mogul is known for his frankness and acts of flamboyance. Earlier this year he had 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, published a front-page letter that finished: “Mr President, please help us.”