Donald Tsang's corruption case is the second of its kind involving top officials in his administration.
Last year, his former chief secretary, Rafael Hui, was found guilty of taking bribes from property tycoon Thomas Kwok.
The former chief executive, who took office in 2005, had long been dogged by criticisms that he and his government were too cosy with the city's powerful tycoons.
Detractors point to how he stopped building new public homes as a sop to property moguls, leading to ever-higher housing prices.
But his supporters note that it was also under the Tsang administration that legislation such as the Competition Law to hobble monopolistic practices was passed. A law banning misleading tactics in property sales went through as well.
An official who used to work with Tsang told The Straits Times that the stopping of land sales was "more a matter of ideology" following the 2003 economic crisis that led to a property crash. "Given his background as a civil servant under the British, Tsang firmly believed in the ideology of non-interference in the market. He was thinking - this is a perfect time to withdraw the visible hand from the market."
Whatever the situation, Hong Kong's image has arguably been affected by the two high-profile cases.