When Tung Chee-hwa was appointed as Hong Kong's chief executive, his backers in Beijing saw him as a rigorous and forthright man with impeccable credentials and an unflinching commitment to economic prosperity.
Mr Tung was chosen by Beijing in 1996
But to his political critics, he has always been seen as a mainland puppet with few leadership skills who has allowed the territory's promised autonomy to be eroded.
And it seems that many of Hong Kong's seven million citizens have not been too impressed either.
When about 200,000 of them took part in a mass demonstration in July 2004 to call for more democracy and to criticise their government, it was evident that Mr Tung had seriously underestimated their strength of feeling.
Especially as this came exactly a year after even more people took part in demonstrations to protest against a proposed anti-subversion bill, which they believed would infringe their political, religious and media freedoms.
Mr Tung went on to withdraw the bill indefinitely, which saw him labelled a lame-duck leader.
China picked the former shipping tycoon from relative obscurity to run the former British colony in 1997.
He took over from the last British governor, Chris Patten, vowing to preserve Hong Kong's freedoms under the so-called "one country, two systems" model.
Whatever his faults, the regional financial crisis that crashed into the territory as soon as he took office was not his doing.
But many believe he fumbled a series of other crises, including the bird 'flu outbreak to the chaos surrounding the delayed opening of the new international airport.
He has been blamed for mishandling the Sars epidemic in 2003 and the territory's economic downturn following the Asian financial crisis.
He was also accused of siding with Beijing in a concerted campaign to erode civil liberties in the territory - with the anti-subversion bill a case in point.
He rejected proposals to discuss making all seats in the Legislative Council directly elected, and warned supporters of Taiwan and Tibetan independence that they were violating the Basic Law, Hong Kong's mini-constitution.
To the horror of many, he also urged democrats to forget the 1989 Tiananmen Square massacre and stop holding annual candle-lit vigils.
His supporters counter that he promised full democracy and has been adopting a gradual approach to its implementation.
They also say he has maintained vital ties with China while steering the territory through unprecedented upheavals.
But signs that he may have slipped in favour with Beijing emerged in December, when Chinese President Hu Jintao used the anniversary of Macau's handover to China to publicly admonish the Hong Kong administration on its performance.
Mr Tung denied, however, during a press conference to announce his resignation, that he had been forced to step down by Beijing.
He insisted that he was resigning for health reasons.
"I will be 68 in three months time and, because of the long hours of schedule - I work 16-18 hours a day - it's taken a toll on my health," he said.
"I've felt this particularly since the third quarter of last year. I felt I get tired very easily, and problems, sickness, crop up here, there and everywhere."
Mr Tung has been building ties with Beijing for a long time.
The Chinese leadership invited him to sit on the committee hammering out the Basic Law in 1985.
Sars has been just one of many crises to beset Mr Tung's rule
He then began taking on various advisory roles for China, and served on Mr Patten's Executive Council for four years.
It was in 1995 that China's plans for him became clear when Chinese President Jiang Zemin sought him out at a photo-call and shook his hand in front of the world's press.
He became chief executive designate in 1996, chosen by a Beijing-picked committee.
Tung Chee-hwa first arrived in Hong Kong as a refugee in 1947, fleeing the Communist advance in China.
He was born in Shanghai in 1937, the son of a powerful shipping magnate, who took his young family to Hong Kong rather than live under Mao Zedong.
He graduated from Liverpool University in 1960 and worked for several years in the United States before returning to Hong Kong in 1969.
Ten years later he became the chairman of his father's shipping empire, Orient Overseas Container Line (OOCL).
But when the company came close to collapse amid a global slump in the mid 1980s, it is widely believed he was bailed out by the Chinese Government.
His many critics say Beijing has owned him ever since.