The astonishing story of the billionaire businessman Jimmy Lai, who became one of Hong Kong’s leading activists for democracy and is China’s most famous political prisoner.

Jimmy Lai escaped mainland China when he was twelve years old, at the height of a famine that killed tens of millions. In Hong Kong, he hustled; no work was beneath him, and he often slept on a table in a clothing factory where he did odd jobs. At twenty-one, he was running a factory. By his mid-twenties, he owned one and was supplying sweaters and shirts to some of the biggest brands in the United States, from Polo to The Limited. His ideas about retail led him to create Giordano in 1981, and with it “fast fashion.” A restless entrepreneur, as Giordano prepared to go public, he was thinking about a dining concept that would disrupt Hong Kong’s fast-food industry. But then came the Tiananmen Square democracy protest and the massacre of 1989.

His reaction to the violence was to enter the media business to push China toward more freedoms. He started a magazine, Next, to advocate for democracy in Hong Kong. Then, just two years before the city was to return to Chinese control, he founded the Apple Daily newspaper. Its mix of bold graphics, gossip, local news, and opposition to the Chinese Communist Party was an immediate hit. For more than two decades, Lai used Apple and Next as part of a personal push for democracy—in weekly columns, at rallies and marches, and, memorably, sitting in front of a tent during the 2014 Occupy Central movement.

Lai took his activism abroad, traveling frequently to Washington, where he was well known in Congress and in political circles. China reacted with fury in 2019 when he met with Vice President Mike Pence and Secretary of State Mike Pompeo. A draconian new security law came into effect in Hong Kong in mid-2020, effectively making free speech a crime and censorship a fact. Lai was its most important target. Apple Daily was raided on August 10, 2020. He was arrested and held without bail before being convicted of trumped-up charges ranging from lighting a candle (“incitement to riot”) to violating a clause in his company’s lease (“fraud”). At the end of 2023, a lengthy trial began alleging “collusion with foreign forces” and printing seditious materials. China’s most famous political prisoner has been in jail for more than 1,100 days and could spend the rest of his life there. The Troublemaker is his story.