1989 – The Hong Kong Alliance in Support of Patriotic Democratic Movements of China forms to back the Tiananmen‑square pro‑democracy rallies and to demand accountability for the June‑4 crackdown[1].

1994 – Hong Kong’s Democratic Party is founded, becoming the city’s longest‑standing moderate pro‑democracy party and later a target of the national‑security crackdown[16].

2019 – Massive anti‑government protests erupt across Hong Kong, prompting Beijing to tighten security controls and later to draft the national‑security law[5].

June 2020 – Beijing imposes the National Security Law (NSL) on Hong Kong, criminalising “subversion, secession, collusion with foreign forces and terrorism” and expanding penalties for dissent[5].

August 2020 – Media tycoon Jimmy Lai is arrested under the NSL for his role in the pro‑democracy movement and the operation of Apple Daily[5].

December 2020 – Lai is placed in custody at Stanley Prison, beginning a five‑year detention that includes prolonged solitary confinement[15].

June 2021 – Police raid Apple Daily’s offices, freeze its assets and force the newspaper to shut, marking a watershed moment for press freedom in Hong Kong[11].

September 2021 – The Hong Kong Alliance votes to disband after its leaders are prosecuted under the NSL, signalling the end of the city’s 30‑year Tiananmen‑vigil tradition[6].

2022 – Pro‑democracy activists Raphael Wong and Figo Chan visit Lai in prison, noting his severe weight loss and deepening Catholic faith[3].

2023 – Jimmy Lai’s high‑court trial on collusion and seditious publishing charges begins, the first major NSL case after the 2019 protests[13].

March 2025 – Hong Kong’s Court of Appeal overturns the 2023 convictions of Chow Hang‑tung, Lee Cheuk‑yan and Albert Ho, resetting the legal backdrop for their new NSL trial[8].

May 2025 – The NSL’s conviction rate approaches 100 %, underscoring its use as a tool to suppress dissent[4].

14 Dec 2025 – The High Court schedules the delivery of verdicts in Lai’s case for 15 Dec, with the media mogul facing two collusion counts and one seditious‑publishing count that carry a life‑sentence maximum[15].

15 Dec 2025 – Jimmy Lai is found guilty of colluding with foreign forces and publishing seditious material; Chief Executive John Lee says Lai’s actions “damaged the country’s interests and the welfare of Hongkongers”[4]. The UK’s Foreign, Commonwealth & Development Office calls the case “politically motivated persecution”[4]. Lai’s daughter Claire tells the BBC she fears she may never see her father again[2].

15 Dec 2025 – In a separate hearing, Chow Hang‑tung and Lee Cheuk‑yan plead not guilty to inciting subversion, while Albert Ho pleads guilty, prompting the court to consider a lighter sentence for Ho[7].

20 Dec 2025 – The High Court again finds Lai guilty on all counts, confirming the earlier 15 Dec verdict and setting the stage for sentencing that could impose life imprisonment[3].

31 Dec 2025 – Claire Lai publicly warns that her father’s health is deteriorating, describing severe weight loss, diabetes, heart issues and “purplish‑grey fingernails that sometimes fall off”[2].

January 2026 (early) – A family letter urges UK Prime Minister Keir Starmer to press Chinese President Xi Jinping for Lai’s release when the two leaders meet later in the month[2].

12 Jan 2026 – A four‑day mitigation hearing opens for Lai and six former Apple Daily executives; prosecutors note Lai’s health is “stable” with only minor weight loss, while defence lawyers argue for reduced starting points of 10‑15 years[10].

13 Jan 2026 – Judges hear sentencing arguments for Lai and the six executives; the panel will set a sentencing date later in the week, with possible penalties ranging from three years to life imprisonment[9].

21 Jan 2026 – The NSL trial of former Tiananmen‑vigil organizers begins; the court notes that the trio’s 2023 convictions were overturned in March 2025, and officials frame the prosecution as “evidence‑based and lawful”[8].

22 Jan 2026 – Opening statements claim the Hong Kong Alliance slogan “bring the one‑party rule to an end” subverts the Chinese constitution; Chow Hang‑tung and Lee Cheuk‑yan plead not guilty, while Albert Ho pleads guilty as the trial, expected to last 75 days, proceeds[1][7].

23 Jan 2026 – Chow Hang‑tung tells the court that the alliance’s call to “end one‑party rule” is a push for democratisation, not an attempt to overthrow the Communist Party[6].

23 Feb 2026 – Hong Kong’s Court of Appeal upholds the jail terms of twelve pro‑democracy activists convicted for “subversion” after the 2020 primary election, with Judge Jeremy Poon declaring, “Nous rejetons l’appel des demandeurs”[17].

Early 2026 (expected) – Sentencing for Jimmy Lai is slated for early 2026, with the possibility of a life‑sentence pending the judges’ final decision[4].