How Jimmy Lai Became Communist China’s Good ‘Troublemaker’

On December 8, 2024, while many people worldwide were busy preparing for the Christmas holiday, Jimmy Lai celebrated his 76th birthday in solitary confinement in a maximum-security jail in Hong Kong. How did this aging media tycoon become one of China’s most high-profile prisoners of conscience? What motivated him? Answers to these questions can be found in a new biography, The Troublemaker: How Jimmy Lai Became a Billionaire, Hong Kong’s Greatest Dissident, and China’s Most Feared Critic.

The book was written by Mark Clifford, who worked closely with Lai for many years. He served on the board of directors of Lai’s media company, Next Digital, until Hong Kong authorities shut the company down in 2021 to punish Lai for his political activism.

Like a typical biography, The Troublemaker tells Lai’s life story from birth to his imprisonment, as well as the ongoing trial. Lai’s advocacy for freedom and democracy is grounded in three key experiences: the poverty he endured in mainland China during his childhood, which instilled in him a distaste for socialism; his remarkable rise from rags to riches in Hong Kong, which fostered his appreciation for economic and political freedom; and his Catholic faith, which provided him with a moral compass and a belief in the inherent dignity of every individual.

What resonates with me the most is Lai’s childhood experience, as I was also born and raised in China. Lai was born into a wealthy family in southern China. However, after the Communists took control of the country in 1949, the local authorities confiscated his family’s property and redistributed it to others. Lai’s father managed to escape to Hong Kong, while his mother was sent to a labor camp. At just eight years old, Lai had to support himself and his younger siblings by working as a porter at a local train station along the Kowloon-Canton Railway.

The railway was one of the few connections between an isolated China and the outside world. Some Hong Kong residents traveled by train, bringing luggage filled with food and essential items to visit relatives in mainland China. Lai observed that visitors from Hong Kong were better dressed and well-fed, which made him realize that the outside world was not as terrible as the Communist Party had claimed. The stark contrast between government propaganda and reality spurred a profound awakening for young Lai. This led him to escape China and move to Hong Kong in 1961, during the Great Chinese Famine.

At age 13, Lai fled to Hong Kong, smuggled on a fishing boat with 40 other mainlanders. The crew hid them in the hold to avoid detection by the British Navy. The journey was so tumultuous Lai later recalled, “everyone was vomiting.”

Years later, he remembered his first breakfast in Hong Kong: “It was the first time I saw so much food. It was the first time I realized food is freedom.” He found work at a garment factory, as his father could no longer support him after remarrying.

Through hard work, Lai founded his clothing company, Giordano, which became known for vibrant, affordable casual wear. When Giordano was listed on the Hong Kong Stock Exchange in 1991, Lai’s incredible journey turned him into a multimillionaire, showcasing the power of resilience and vision.

Lai distinguished himself among Hong Kong’s wealthy elite due to his deep interest in political philosophy alongside his passion for making money. He credited influences like Austrian-British economist and political philosopher Friedrich Hayek, particularly his book The Road to Serfdom, which warned about the threats of socialism and inspired Lai to champion the cause of freedom.

His pivotal moment came in 1989 when demonstrators, primarily college students, led a pro-democracy movement in Tiananmen Square in Beijing. Lai joined fellow Hong Kong residents in supporting the protests by raising donations and producing T-shirts for the participants. The Chinese Communist Party’s brutal crackdown on the demonstrators on June 4 served as a wake-up call for many in Hong Kong, including Lai.

Lai went on to found a media empire, including the Next magazine and Apple Daily, which criticized the Chinese Communist Party (CCP) and advocated democracy and free markets. In a column, he declared: “Yes, I am anti-Communist. I am completely opposed to the Communist Party because I disdain all things that restrict personal freedom.” His publications were credited for fostering political and civic engagement of the city’s seven million residents and helping mobilize hundreds of thousands, and eventually millions to take part in the city’s various pro-democracy protests between 2003 and 2019.

Lai’s advocacy was further strengthened by his conversion to Catholicism in 1997. As noted by Chris Patten, Hong Kong’s last British governor, the city’s Catholic community played a significant role in promoting democracy and freedom in Hong Kong, largely due to its strong belief in human rights and the dignity of individuals.

Jimmy Lai didn’t just talk about democracy and freedom through his media empire; he was often seen on the front line of various pro-democracy demonstrations in Hong Kong. He also used his international connections to lobby foreign leaders, including former Secretary of State Mike Pompeo, to impose sanctions on Chinese officials who violated the human rights of Hong Kong residents. Lai’s political activism distinguished him from other wealthy individuals in Hong Kong, many of whom chose to remain silent in exchange for business favors from Beijing.

Lai was fully aware of Beijing’s intolerance towards critics, yet he remained defiant. Despite the safety offered by his British passport and overseas properties, he chose to stay in Hong Kong. His unwavering belief in his duty as a resident and a Christian drove him to be prepared to sacrifice himself for what he considered a noble cause.

Labeled a “troublemaker” by Hong Kong authorities, Lai was jailed on December 31, 2020, under the harsh National Security Law. A year later, Hong Kong police raided Apple Daily, arrested six staff members, and permanently shut down the newspaper and Lai’s Next Media company.

Since his arrest, Lai has been placed in solitary confinement. He often spends his time in prison drawing Christ on the cross and the Virgin Mary. During his four-year imprisonment, he has been sentenced multiple times for participating in rallies in 2019 and for lighting a candle to commemorate the Tiananmen Massacre on June 4, 2020. The trial for the most serious charges against him, including “colluding with foreign forces,” began in mid-December 2024. If convicted, Lai could face the possibility of spending the rest of his life in prison.

This book serves many purposes. It chronicles the contemporary history and the evolving relationship between China and Hong Kong. It acts as a cry for help, as Lai’s family and supporters have been trying to rally international pressure on Beijing to secure his release. Additionally, it serves as a stark warning that the Chinese Communist Party (CCP) cannot be trusted. Despite their promise to maintain Hong Kong’s economic and political freedoms for 50 years, the CCP has systematically stripped away much of the city’s and its residents’ rights and freedoms.

Above all, Jimmy Lai’s extraordinary life story and courageous political activism should inspire us to follow his example. Freedom is worth fighting for — even if it means risking becoming a troublemaker in the eyes of the authorities.