Leung Chun-ying – ubiquitously known as "CY" – launched his campaign on November 27, 2011, with a message of change.
He stood for a turn away from tycoon-friendly policies that were alienating many of Hong Kong's 7 million residents and adding to the city's gaping divide between rich and poor.
The small group of supporters that came to hear Mr Leung speak, however, consisted mostly of business people, including property tycoon Vincent Lo, who had been nurtured by the Chinese Communist Party's "united front" apparatus and given privileged access to the mainland marketplace. In other words, they were his natural constituency. They were just like him.
It was the support of this group of business tycoons and underground party officials that steered Mr Leung to an unlikely victory in the 2012 contest to be the city's chief executive. And it was arguably the opaque culture of this group that explains how Mr Leung chose not to declare a massive windfall agreement signed just five days after launching his campaign.
Mr Leung has said through a spokesman and his lawyers that there is nothing improper about the 4 million pound payments that he received from the Australian purchaser of his company, UGL, during his term as chief executive, while other shareholders lost their money.
Fairfax has published the documents in full and left it to others to decide.
Politically, however, the lack of transparency puts him on shaky ground.
Mr Leung's receipt of hidden payments symbolises a lack of respect that has pushed tens of thousands of protesters onto the Hong Kong streets in the past 10 days.
Ostensibly, the tens of thousands of students and supporters have been fighting to hold leaders in Beijing and Hong Kong to their promise of introducing "universal suffrage" elections in 2017, which is something the British were unable to deliver.
Deep down, however, their fight is not really about changing the status quo, but defending it.
They are fighting to defend the robust institutions of civil society that have made Hong Kong one of the most vibrant and successful cities in the world.
They are demanding that Mr Leung defend the city's enviable independent courts, police, schools, universities and media against the unrelenting pressure from Beijing.
They are also defending home-grown institutions, such as the Independent Commission against Corruption, which helped to keep the city's marketplaces clean.
The political danger of Mr Leung's decision not to expose his financial arrangements to open debate is that it can be seen to represent an indifference to the demands of Hong Kong's modern, pluralistic and democratically-minded society.
His hidden dealings will do nothing to dampen growing protester demands that he resign.
