In 2001, he received a medal of honour for civic education around the Basic Law, Hong Kong's mini-constitution which has governed the former British colony since it was handed over to China.
More than 20 years later, he has received the longest prison term among the 45 pro-democracy figures charged with subversion under a sweeping national security law imposed by Beijing.
Dressed in a dark suit, his once black hair now silver, Tai seemed in good spirits on Tuesday, smiling in the defendant's dock.
The 60-year-old saw his sentence reduced by one-third due to his earlier decision to plead guilty.
Judges on Tuesday wrote that Tai was the "initiator" of a scheme to undermine the Hong Kong government and the "organiser" of a 2020 primary election to coordinate the pro-democracy camp.
"(Tai) was the mastermind," the judges wrote.
After Hong Kong's massive, sometimes violent protests in 2019 were quashed, Tai developed a strategy to unite Hong Kong's disparate pro-democracy groups into a coalition to seek a legislative majority.
If they succeeded, they would veto government budgets, forcing it to accede to demands raised by protesters and ultimately push for the city's leader to step down, prosecutors said.
Tai had argued the move fell within the Basic Law, which enshrines the city's unfulfilled right to universal suffrage.
Days after he pleaded guilty in the subversion case in 2022, the government stripped him of the medal of honour.
- Shift to activism -
Born in 1964, Tai studied law at the flagship University of Hong Kong at a time when the UK and China were entering the final phase of negotiations on the city's handover.
His thesis examined Beijing's "One Country, Two Systems" political framework that allowed Hong Kong to preserve its capitalism, a common law system and certain civil liberties.
After graduating, Tai assisted Martin Lee, founder of Hong Kong's Democratic Party, to draft the Basic Law, before leaving for postgraduate studies in London.
For more than two decades after his return, he was a celebrated law professor and a well-respected scholar sitting on the government's civic education committee.
But as Tai pursued his idea for a universal suffrage sit-in, he shifted more towards public activism.
He spearheaded the Occupy Central movement in 2014, where hundreds of thousands of Hong Kongers staged a 79-day sit-in around the city's Central business district, calling for universal suffrage.
They faced 87 rounds of tear gas and authorities rejected their demands.
"I shall never give up and I will definitely continue to pursue democracy for Hong Kong," Tai told the court after being convicted on incitement and public nuisance charges in 2019.
- 'Hong Kong's fall' -
Soon after his release on bail in August 2019, as pro-democracy protesters were besieged by police at a local university, candidates avowing their cause recorded a landslide win in District Council elections.
Tai, a self-described "bridge-maker" among the democratic movements, saw an opportunity to secure a legislative majority.
"Elections... cannot change the undemocratic nature of the political system," he wrote in his book "Love and Peace: The Unfinished Journey of Resistance".
But "they can slow down Hong Kong's fall into full-fledged authoritarian rule".
Activist Raphael Wong said Tai wanted "to absorb, coordinate and integrate various opinions from the vast political spectrum of the democratic camp".
Today, many activists have either been arrested or left the city.
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