billionaire tested China
They had all been part of the turbulent protests that had rocked Hong Kong in 2019, when hundreds of thousands took to the streets demanding democracy and more freedom in the Chinese territory.
They would also often meet for dinner, sometimes lavish meals, gossiping and bantering over dim sum, pizza or claypot rice.
In prison, he "loved eating rice with pickled ginger," Chan said. "No-one could have imagined Jimmy Lai would eat something like that!"
But neither had they imagined a reunion at a maximum security prison, the protests crushed, friends and fellow activists jailed, Hong Kong just as boisterous and yet, changed. And gone was the owner of the irreverent nickname "Fatty Lai": he had lost considerable weight
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Decades apart - Lai in his 70s, Wong and Chan about 40 years younger - they had still dreamed of a different Hong Kong. Lai was a key figure in the protests, wielding his most influential asset, the hugely popular newspaper, Apple Daily, in the hope of shaping Hong Kong into a liberal democracy.
That proved risky under a contentious national security law imposed in 2020 by China's Communist Party rulers in Beijing.
Lai always said he owed Hong Kong. Although he is a UK citizen, he refused to leave.
"I got everything I have because of this place," he told the BBC hours before he was arrested in 2020. "This is my redemption," he said, choking up.
He wanted the city to continue to have the freedom it had given him. That's what drove his politics - fiercely critical of the Communist Party and avowedly supportive of Hong Kong's pro-democracy movement. It cost him his own freedom.