A Hong Kong court sentenced the pro-democracy media tycoon Jimmy Lai to 14 months in prison Friday, after finding him guilty of “unauthorized assembly” during pro-democracy protests in 2019.

A new, additional charge was also lobbed at him Friday: two counts of “colluding with foreign forces,” which carries a maximum penalty of life in prison.

Nine other of the city’s top pro-democracy campaigners were also sentenced alongside Lai Friday to up to 18 months in prison for their involvement in the same two 2019 protests.

They are the most prominent and influential Hong Kong figures to be sent to jail thus far since Beijing enacted a draconian National Security Law (NSL) in the territory last summer, brought down in response to those protests and others that continued up until early last year. Eight of those defendants are over the age of 60, each known for their role in shaping Hong Kong law and politics since the end of British rule in 1997.

Lai, 73, is a long-standing critic of Beijing and founder of the loudly and proudly pro-democracy Apple Daily local newspaper.

Earlier this week, his paper published his first public comments in months: a handwritten letter to his staff that he wrote from prison, which stated that “it is our responsibility as journalists to seek justice.”

“The era is falling apart before us, and it is time for us to stand tall,” he wrote. But he also urged them not to take undue risks, noting: “Freedom of speech is a dangerous job.”

More than 10,000 have been arrested in relation to the 2019 protests, most of whom are out on bail awaiting trial. That movement is the subject of “Do Not Split” from Norwegian director Anders Hammer, which will compete for the best documentary short Oscar next weekend.

Around 50 other lawmakers and activists involved in helped pro-democratic parties win local elections were arrested in January under what was then the broadest use of the NSL to date.

At the hearing Friday, the judge declared that the defendants had “deliberately defied the law” by participating in the protests, undertaking actions that were “a direct challenge to the authority of the police, and therefore law and order.”

The charge of organizing and participating in an unauthorized assembly carries a max sentence of five years in jail.

Some of the oldest defendants receive suspended sentences, meaning that they won’t have to serve jail time if they commit no further crimes in the next two years.

They include veteran barrister Martin Lee, 82, who has been called Hong Kong’s “father of democracy,” and lawyer Margaret Ng.

Ng, 73, roused applause from spectators present at the hearing with a speech in which she reiterated her commitment to and the legitimacy of Hong Kong’s democratic rights.

“When the people, in the last resort, had to give collective expression to their anguish and urge the government to respond, protected only by their expectation that the government will respect their rights, I must be prepared to stand with them, stand by them and stand up for them,” she said.

Earlier this month, Beijing made broad changes to Hong Kong’s electoral rules to cement greater control over the process.

Friday’s court ruling comes in the wake of Hong Kong’s first National Security Education Day on Thursday, which was marked with “patriotic education” in the form of parades featuring soldiers marching in Chinese goose-step rather than British style, counterterrorism drills, in-school propaganda, and even expensive toy souvenirs celebrating the police force, such as teddy bears in riot gear.

Hong Kong’s newspapers Thursday all published the same full, front-page color ad from the education ministry emblazoned with the statement “Uphold National Security, Safeguard Our Home.”

Only Lai’s Apple Daily declined, instead running a front-page report on a local case of child abuse.