A small electoral college chooses a new Hong Kong on Sunday amid accusations of meddling by Beijing, denying the Chinese-ruled financial hub a more populist leader perhaps better suited to defuse political tension.
The vast majority of the city's 7.3 million people have no say in their next leader, with the winner to be chosen by a 1,200-person "election committee" stacked with pro-Beijing and pro-establishment loyalists.
Three candidates are running for the top post, two former officials, Carrie Lam and John Tsang, and a retired judge, Woo Kwok-hing. Lam is considered the favorite. (For a graphic on candidates in the running click tmsnrt.rs/2nLcvnd)
"I hope we all remember on 24 March 2017, we Hong Kong people have all come together and given our most sincere blessings for a more united, a better Hong Kong," Tsang told a rally of thousands of cheering on Friday night.
Mass protests are planned over the weekend denouncing Beijing's "interference" in the election amid widespread reports of lobbying of the 1,200 voters to back Lam, rather than the more populist and conciliatory former finance chief, Tsang.
Since Hong Kong returned to Chinese rule in 1997, Beijing has gradually increased control over the territory even though Beijing promised wide-ranging freedoms and autonomy under the formula of "one country, two systems", along with an undated promise of universal suffrage.
Many fear that Lam will continue the tough policies of staunchly pro-Beijing incumbent Leung Chun-ying, a divisive figure who ordered the firing of tear gas on pro-democracy protesters in 2014 and who wasn't seen to be defending Hong Kong's autonomy and core values.
The political upheavals with Beijing over the city's autonomy and democratic reforms - that many hoped would have allowed a direct election this time round - have roiled a new generation and weighed on the city's economy, ranked 33rd globally by the World Bank in 2015.
Political and social divisions, mainly over democracy and anxieties over China's creeping influence, have dominated political debate leading to some legislative and policy-making paralysis and the stalling of major projects, including a cultural hub and high-speed rail link to China.
Businesses have also faced growing competition from mainland Chinese firms in core sectors like services and property. Housing prices, now among the world's highest, are widely seen to have been jacked up by an unrelenting wave of buying from rich Chinese, intensifying anti-China sentiment.
Many observers, leading businessmen and politicians have warned Hong Kong can't afford another period of upheaval if the city is to regain its former capitalist mojo.
Beijing's shadowy detention of five Hong Kong booksellers in late 2015, and the disappearance of a Chinese billionaire this year, have also undermined confidence in "one country, two systems" formula.
While Beijing hasn't explicitly backed any candidate, senior officials have stressed certain conditions must be met including a new leader having the "trust" of China's Communist leaders.
"Just because a candidate is leading popularity polls doesn't necessarily mean you should vote for (that person)," said Leung Chun-ying on Friday.
Nearly 2,000 police will be stationed around the harbourfront voting center in case of any unrest.