His two primary titles — the Apple Daily newspaper and the digital-only Next magazine — openly back democracy protests in a city where competitors either support Beijing or tread a far more cautious line.
The two publications have been largely devoid of advertisements for years as brands steer clear of incurring Beijing’s wrath, Lai plugging the losses with his own cash.
But they are popular, offering a heady mix of celebrity news, sex scandals and genuine investigations such as a recent series looking at how the houses of some senior police officers violated building codes.
Lai said he was determined to stay in Hong Kong even once the security law came in.
“The only thing we can do is persist, not to lose spirit or hope,” he said. “And to think that what is right will eventually prevail.”
Asked why he risked both his wealth and freedom by criticising Beijing and publicly supporting Hong Kong’s democracy movement, he replied: “I’m a troublemaker.
“I came here with nothing, the freedom of this place has given me everything. Maybe it’s time I paid back for that freedom by fighting for it.”