As night fell, chaos erupted when crowds of protesters outside Hong Kong's legislative building hurled bottles at police, who fired pepper spray and swung batons, dragging some people to the ground.

It was a shocking descent into violence from what began as a peaceful march, attended by more than a million people by some estimates -- roughly one in seven of the city's population -- to oppose a bill that would have allowed the extradition of criminal suspects to mainland China.

It was June 9, 2019 -- and Hong Kong was about to change forever, as it plunged into months of mass protests, bloody street battles and an unprecedented crackdown by authorities that saw Beijing tighten its grip on the city with a sweeping national security law.

Last week, the man who led the crackdown stepped onto a stage to lay out his vision for Hong Kong -- this time not as the city's security chief, but its next leader.

John Lee speaking at an interview in Hong Kong on September 17, 2021.

John Lee, who became the face of the national security law and who oversaw the arrests of dozens of activists and raids on newsrooms, is set to replace outgoing Chief Executive Carrie Lam when she finishes her five-year term at the end of June.

In what the government billed as an "open, just and honest" election, a largely government-appointed, pro-Beijing committee of 1,461 people appointed the next leader for the city's 7.5 million residents on Sunday. Lee was the only person in the running, in contrast to previous years that saw run-offs between multiple candidates.
For many, Lee's ascension speaks volumes about the direction Hong Kong -- once world-renowned for its robust press, flourishing civil society and democratic aspirations -- is headed. Lee has already indicated that he will look to introduce further national security legislation and possibly a law against fake news.
To Nathan Law, a human rights activist and former local lawmaker now in self-exile in Britain, it seems "very obvious" why Lee is tipped for the role.
"It really signals (authorities) are intensifying that heavy-handed approach to Hong Kong, and putting the so-called national security as their policy for governing the city," Law said.
A rise years in the making
The forces behind Lee's rise to the city's top job can be traced back nearly half a century.
Lee joined the Hong Kong police force as a 19-year-old recruit in 1977 as the city -- then a British colony -- underwent an economic transformation into a modern financial center.
He rose through the ranks and was promoted to chief superintendent in 1997 -- the same year Britain handed the city to China in a pomp-filled ceremony watched around the world.
Since that watershed year, activists like Law say they have watched Hong Kong's freedoms be squeezed ever tighter. All the while, Lee continued gaining prominence, becoming deputy commissioner, the second-highest position in the police force, by 2010.

Just two years after that, he joined the city's Security Bureau as under-secretary. To some, the appointment of a high-ranking police officer to a key government office was a statement of intent.

"We were already really nervous about that, because that really signaled a change in Hong Kong's policy, changing it in a seemingly more suppressive way," Law said.

By 2016, when Law was elected into the legislature, Lee "was already notoriously difficult to deal with" and seemed hostile to any journalists or opposition lawmakers who raised questions or challenges, Law said.

Lee's supporters have disputed this characterization, maintaining his time in the police force helped prepare him for a public office.

One pro-Beijing lawmaker, Ma Fung-kwok, said Lee had demonstrated "leadership skills" in his handling of the protests and the pandemic, according to public broadcaster RTHK. Another, Jeffrey Lam, said Lee had "solved many cases" in the police force and can cooperate with "other sectors in the society."

At a brief political rally on Friday, Lee, whose slogan is "We and us -- a new chapter together," stressed the importance of community and promised to "make Hong Kong a place of hope" once appointed.

CNN has reached out to Lee's campaign team for comment.

The 2019 protests

Lee's rise continued when he was appointed security chief in 2017 -- the "beginning of a changing trend," said Joseph Cheng, a retired Hong Kong academic and pro-democracy activist now based in New Zealand.

"Beijing seems to be emphasizing loyalty more, or the capability of implementing a hard line -- therefore, senior officials from the disciplinary forces appear to occupy a more advantageous position," Cheng said.

It was under Lee's tenure that the Security Bureau introduced the controversial extradition bill that led to the protests in 2019.

Critics worried Beijing could use the bill to prosecute Hong Kong residents for political reasons under China's opaque legal system.

Protesters march against a proposed extradition bill on June 16, 2019 in Hong Kong.

With the Hong Kong government standing firm on the bill despite public objections, the protests quickly expanded into a broader pro-democracy, anti-government movement. Fears were underpinned by widespread anxiety about Beijing's growing influence and the perceived erosion of Hong Kong's cherished semi-autonomous status, which allowed it the freedoms of press, speech and assembly that had long been central to its international appeal.

Withdrawing the bill was just one of five popular demands by protesters; others included universal suffrage and accountability from police, who faced accusations of brutality they have denied.

At the height of the crisis, protesters and police clashed nearly every week, with demonstrators lobbing bricks and Molotov cocktails and officers responding with tear gas, rubber bullets, and at times live ammunition. The violence polarized the city, cementing the breakdown in trust between the public and the authorities.

A protester throws back a tear gas canister fired by police in Hong Kong on October 1, 2019.

Through it all, Lee praised his officers as "courageous" and condemned protesters as "radicals" who were sowing "terror." When hundreds of protesters -- many high school students -- occupied a university for more than a week, police laid siege to the campus with Lee declaring: "We will arrest them all."

Lee has repeatedly defended the force's actions, insisting critics need to "think about the (preceding events), otherwise it will not be fair."

"I am proud of the Hong Kong police force. They remain Asia's finest ... Compared to what they do with law enforcement agencies overseas, I think they have exercised restraint. They have minimized the harm and injuries to everybody," he said in September 2019.

Long arm of the national security law

Lee gained local prominence for his role in combating the protests -- but his implementation of the national security law cemented his reputation as a hardline enforcer and Beijing loyalist.

The security law was promulgated by Beijing in June 2020, during a lull in the protests brought by the Covid-19 pandemic. Described by the Hong Kong government at the time as "a crucial step to ending chaos," the law criminalizes secession, subversion, terrorism and collusion with foreign forces -- and allows for maximum sentences of life imprisonment.

In an instant, Hong Kong's social and political landscape was transformed, and within months, many of the city's leading pro-democracy figures were either in jail or exile.

Police officers raid the Apple Daily headquarters in Hong Kong on August 10, 2020.

Under the security law, Lee oversaw the mass arrest of opposition figures in 2021, accusing them of trying to "paralyze the Hong Kong government" by organizing a pro-democracy primary election.

He ordered a police raid on Hong Kong's biggest pro-democracy newspaper, Apple Daily, which was subsequently forced to shut after its assets were frozen and several employees arrested under the security law.

A week after the raid, Lee was promoted to chief secretary -- the second-highest position in government -- and the first time a security official has taken the role.

Experts say Lee's suppression of the protests and support for national security is precisely why he now finds himself the city's next leader.

"(This is) the reward for loyalty," said Cheng, the activist and former academic.

Supporters of the security law insist it has helped establish stability in the wake of the violence and political unrest of 2019. "People's lives and property are protected, and they can once again enjoy their legitimate rights and freedoms," a government spokesperson said in April in response to a question on the law.

But Lee's association with the law has been met with increasing scrutiny abroad. He was among nearly a dozen people sanctioned by the US in 2020 for undermining the city's autonomy and democratic processes -- which Lee has scoffed at, recently calling the sanctions "unreasonable" and "acts of bullying."

He has also continued to defend the law, as well as recent electoral changes that placed him at the head of a vetting committee to screen all candidates, ensuring only "patriots" would be allowed to run for office.

The national security law "has restored peace," Lee told the United Nations Human Rights Council in March, decrying the 2019 protests as "evil" and lauding "the improved electoral system."

"No country has a monopoly on the model of democracy," he added.

What this means for Hong Kong

Lee has already made clear the kind of government he will shape: one with increasingly close ties to mainland China.

At the unveiling of his policy manifesto on April 29, Lee emphasized the need to integrate Hong Kong with other economically important Chinese cities. There was no English translation provided, despite English being one of Hong Kong's two official languages -- in striking contrast to most government events to date.

He also vowed to bolster security legislation and introduce "national identity" education. Both proposals have long been controversial, with previous attempts to introduce legislation foiled by protests and pushback -- much to Beijing's frustration.

Lee has also previously voiced support for a "fake news" law -- prompting fears the reins will only tighten on what remains of the city's media and civil groups. Last week, the city's press freedom ranking plunged to a record low of 148 among 180 locations, compared to its ranking of 73rd in 2019.

Despite this, the outgoing Chief Executive Lam continues to claim that Hong Kong's media sphere is "as vibrant as ever," though she warned last week that "media organizations are not above the law ... including the national security law."

Lee will also have to navigate the Covid-19 pandemic, with patience fraying among many in Hong Kong after more than two years of stringent restrictions in accordance with China's unbending zero-Covid policy.

At his policy manifesto event, Lee asserted that "at some point (the virus) will be under control," and that he would design measures to allow businesses to operate.

Cheng, the pro-democracy activist who moved to New Zealand, sees the future as being "the continuation of the hard line of the past two years."

"There is no toleration of political opposition ... there will be very little tolerance of an independent media, and very little tolerance for the operation of civil society organizations," Cheng said.

When asked by CNN about accusations of diminished political freedoms, a government spokesperson responded that the rights of Hong Kong residents are "protected in accordance with the law" -- but that "many freedoms and rights are not absolute, and can be restricted for reasons including protection of national security and public safety."

Disillusionment and emigration

Among former activists and pro-democracy supporters, there's a sense of despair as Lee prepares to take office.

The circumstances of his selection, with Lee as the sole contender showered with praise by pro-Beijing lawmakers, cut particularly deep for many of those who once marched to demand greater democratic freedoms.

"It's definitely not, by any means or any parameters, a democratic (process)," said Law, the former lawmaker. "It's really just an appointment. I don't really call it an election."

Lee has dodged questions about whether he was handpicked by the central Chinese government, saying in April he welcomed anybody else who wished to run.

He has since received endorsements from leading establishment figures, including two former police commissioners and two former security chiefs, RTHK reported.

After the turmoil of the past three years, even a new administration is unlikely to bridge the broken relationship between the government and its people, said John Burns, emeritus professor at the University of Hong Kong.

"There is a huge percentage of the population that is alienated and angry," he said, pointing to mass emigration as "evidence of alienation ... of a sick society."

Locals, expatriates and foreign companies are leaving the city in droves. More than 100,000 Hong Kongers applied for a new visa offering a path to citizenship in Britain last year; and in February and March alone this year, more than 180,000 people left the city while only about 39,000 entered, according to immigration data.

While Hong Kong's harsh Covid restrictions are helping drive this exodus, Lee's critics say that so too is the crackdown on civil liberties he enforced.

Asked about this on April 29, Lee brushed it off. He claimed Hong Kong had always seen high levels of mobility, and that its proximity to the mainland market would continue to attract businesses.

"We are an inclusive city," he told reporters. "Together, we start a new chapter for Hong Kong."