He briefly worked with the graft-busters during the Independent Commission Against Corruption's toughest days in the 1970s. But yesterday, former chief secretary Rafael Hui Si-yan found himself on the other side of the fence, as a target of an ICAC investigation.
With political nous that earned him the nickname 'king of strategy', the 64-year-old veteran civil servant was seen as the most trusted aide to Chief Executive Donald Tsang Yam-kuen, who entrusted him with the city's No2 job after he was elected in 2005.
Tsang described Hui - who kept a deliberately low profile at the helm of Tsang's administration - as someone he could work well with, with the seniority to lead the governing team.
He was also seen as a close friend of his successor as chief secretary, Henry Tang Ying-yen, and observers were shocked that he was not named as a key strategist in Tang's ill-fated campaign for chief executive.
His arrest yesterday, along with brothers Thomas Kwok Ping-kwong and Raymond Kwok Ping-luen of the Sun Hung Kai Properties empire, rocked the city.
Hui, who is said to have advised Tsang during the 1997 Asian financial crisis to take action and stabilise the market, had hoped to be remembered as Hong Kong's steady hand in a time of crisis. Now his otherwise luminous career appears to be in ruins.