Jimmy Lai, Communism, and the Tall Poppy Syndrome.
The difference between freedom and tyranny is only a matter of dates. Alexandre Dumas
Most people view Tall Poppy Syndrome (TPS) as an interpersonal phenomenon. Governments play a significant role in TPS and often seem to avoid accountability for their actions and misdeeds. In fact, the original descriptions of TPS by Herodotus, Aristotle, and Livy involved governments cutting down political opposition (see Livy, Tarquin the Proud, & The Tall Poppy Syndrome).
Many think the "ism" governments are the greatest offerders and while that may be true, democratic governments are offenders as well especially their three-letter agencies such as the FBI (see Navalny-Skripal-Prigozhin: Courage and the Tall Poppy Syndrome).
Journalism has been a subject of interest in my blogs because the entity cuts both ways - as a cutter and cuttee (Journalism as Cutter and Cuttee in the Tall Poppy Syndrome).
Macau and Hong Kong were both European colonies returned to Chinese sovereignty under “one country, two systems,” but Hong Kong’s post‑handover trajectory has been far more contentious and politically turbulent than Macau’s, which has remained comparatively quiescent and accommodating to Beijing.
Portuguese traders established a permanent settlement at Macau in 1557 during the Ming dynasty, and it evolved into a small entrepôt under varying degrees of Portuguese control for over four centuries. China and Portugal signed a Joint Declaration in 1987, setting a transition period leading to the formal transfer of sovereignty to the People’s Republic of China (PRC) on 20 December 1999.
At midnight that day, Portuguese rule ended after roughly 442 years, and Macau became the Macau Special Administrative Region (MSAR) under Chinese sovereignty, with a promise that its existing capitalist system and way of life would remain unchanged for 50 years.
Britain acquired Hong Kong Island in 1841 during the First Opium War, later expanding control to Kowloon and the New Territories, creating a major colonial trading and financial center over about 156 years of British rule. The key driver of change was the 99‑year lease on the New Territories, expiring in 1997, which led to the Sino‑British Joint Declaration of 1984, which set the terms for the handover.
On 1 July 1997, sovereignty was transferred to the PRC, and Hong Kong became the Hong Kong Special Administrative Region (HKSAR), with a Basic Law promising a “high degree of autonomy” and preservation of its social and economic systems for 50 years, until 2047.
Thereafter, the handovers diverged. Hong Kong developed a more assertive civil society and pro‑democracy movement, leading to repeated mass protests and Beijing’s subsequent tightening of control, including reinterpretations of the Basic Law and new security measures; Macau has seen far fewer and smaller protests, with local politics more consistently aligned with Beijing.
Hong Kong’s distinct political identity and a larger, more vocal activist and professional class have produced visible resistance to perceived encroachments on autonomy; Macau’s smaller population, heavier economic dependence on mainland tourism and casinos, and different colonial legacy have translated into weaker mobilization and relatively smoother integration.
The 2019 protests were triggered by a proposed extradition bill put forward by the Hong Kong government, which would have allowed criminal suspects in Hong Kong to be transferred to jurisdictions with which it had no formal extradition treaty, including mainland China. Many residents feared this would undermine Hong Kong’s judicial independence and expose activists, journalists, and businesspeople to the mainland legal system, seen as more opaque and politically influenced.
Protests began in spring 2019 with large marches against the bill, escalated after police used force against demonstrators, and evolved into a broader movement demanding full withdrawal of the bill, an independent inquiry into police conduct, amnesty for arrested protesters, retraction of the characterization of protests as “riots,” and genuine universal suffrage.
Jimmy Lai is a self‑made Hong Kong media tycoon turned prominent pro‑democracy figure who is now one of the most high‑profile defendants prosecuted under the PRC‑imposed national security regime in Hong Kong.
Lai (Lai Chee‑ying) was born in 1947 in Guangzhou to a family that lost its wealth after the Communist takeover; at about 12, he was smuggled into Hong Kong as an undocumented migrant and worked in factories. He rose from child laborer to clothing entrepreneur, founding the Giordano casual‑wear chain in 1981, which expanded into an international brand before he sold his stake in the mid‑1990s under political pressure from Beijing.
The 1989 Tiananmen Square crackdown radicalized Lai politically. Giordano printed T‑shirts supporting the protesters, and he began denouncing the Beijing leadership, which catalyzed his shift from garments to media.
In 1990, he founded Next Magazine, and in 1995, he launched the tabloid‑style Apple Daily, which mixed sensational news with hard‑hitting political coverage and became one of Hong Kong’s most influential newspapers. He later expanded his media ventures to Taiwan through local editions of Next Magazine and Apple Daily, consolidating a cross‑border media empire.
After 1989, Lai became an outspoken critic of the Chinese Communist Party and a major financial backer of Hong Kong’s pro‑democracy camp, including support for the Democratic Party and other activists. Apple Daily and Next Digital consistently championed press freedom, criticized both the Hong Kong and Beijing authorities, and gave prominent coverage to pro‑democracy protests, making Lai a central symbolic figure of opposition.
He personally participated in demonstrations, met foreign politicians and officials, and advocated stronger international attention to Hong Kong’s autonomy and rights, which Beijing later framed as “collusion with foreign forces.”
Lai was first arrested under Hong Kong’s new national security law in August 2020 on suspicion of “collusion with foreign forces,” and police simultaneously raided Apple Daily’s newsroom; he also faced separate charges, including unlawful assembly and fraud. Authorities froze his media company’s assets, several senior editors were arrested, and Apple Daily was forced to close in 2021 after its accounts were blocked and staff prosecuted, effectively dismantling his media group.
In a major national‑security trial before a specially designated panel of judges (with no jury), Lai was found guilty of offences including collusion with foreign forces and sedition related to his media work, public statements, and alleged lobbying of foreign governments.
In early 2026, at age 78, he received a 20‑year prison sentence, on top of earlier shorter sentences for other offenses, making him one of the highest‑profile and most severely punished pro‑democracy figures in Hong Kong. The length is essentially a death sentence because of his age.
It also confirms that Hong Kong is under the iron fist of the PRC. The promise of Hong Kong's autonomy for 50 years was and is now a confirmed pipe dream, leaving five million people under the control of a totalitarian government.
Lai’s life traces a path from refugee factory worker to billionaire entrepreneur, then to media mogul and democracy advocate, and finally to being treated by the PRC and Hong Kong governments as a national‑security offender whose case has become a focal point for global debates over the city’s political freedoms.
It is the quintessential case of TPS and the path to tall poppydom, highlighting courage and servitude. Long live tall poppies everywhere.
I have completed writing my new book, Sin to Virtue: Transforming The Tall Poppy Syndrome by Understanding The Seven Deadly Sins. Here's a preview:
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