Hong Kong's former leader Donald Tsang Yam-kuen became the city's highest-ranked official to be put behind bars after he was sentenced on Wednesday to 20 months in prison for misconduct.
The city's former chief also faces a retrial, tentatively set for September, for a bribery charge that the jury failed to reach a verdict on last week.
Tsang closed his eyes as he heard his fate, while his family members in the public gallery appeared to be fighting back tears. His wife of almost 50 years, Selina Tsang Pou Siu-mei, cried after hearing her husband would be imprisoned.
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Mr Justice Andrew Chan Hing-wai cut Tsang's sentence to 20 months from an original 30, giving him credit for a life dedicated to public service, reinforced by a range of letters that "all speak with one voice to his commitment to servicing the people of Hong Kong".
"Never in my judicial career have I seen a man fallen from so high," Mr Justice Chan said during sentencing, as Tsang stood in the dock.
"In the present case, the seriousness lies in the position the defendant occupied: the office of the chief executive."
Chan said Tsang had breached the trust placed in him by both the people of Hong Kong and the people of China.
After hearing the sentence, Selina Tsang, flanked by her two sons, walked slowly out of the courtroom, rubbing her eyes briefly before entering the conference room next door.
Sitting down, she could no longer hold back her tears, wiping them away with a piece of tissue paper.
Her sorrow was visibly shared by defence counsel Clare Montgomery QC, who repeatedly sighed, shook her head and momentarily covered her face with both hands while speaking to the family.
Montogmery had said in court that there could be a possible appeal on the misconduct charge, but when asked later if she would be filing a bail application for Tsang pending the appeal, she replied: "I won't be commenting on anything."
Earlier that morning, Tsang was escorted in chains to a prison van by correctional officers as he was taken from Queen Elizabeth Hospital to the Hight Court to await sentencing.
Though he had been stretchered into hospital on Monday in the blue jumper that is standard attire for all prisoners, the ex-chief executive was back on his own feet on Wednesday morning and once more sporting his signature bow tie.
Tsang, 72, spent the past two days in custody. He was admitted to Queen Elizabeth Hospital's custodial ward on Monday night with a severe cough.
Drama ensued outside the courtroom on Wednesday as Tsang's wife Selina Tsang Pou Siu-mei, son Thomas Tsang Hing-shun, and siblings Katherine Tsang King-suen and Tsang Yam-pui arrived and were instantly mobbed by a media pack.
Thomas Tsang had made his way to the court on foot. At one point a cameraman was knocked over, but Tsang's son paused to reach down and help him up.
Otherwise, most of the family came in public cars rather than government vehicles, and there was no sign of any bodyguards, though Tsang and his family were usually accompanied by about eight bodyguards in dark suits when they turned up at court on previous occasions.
Before the sentencing session began, the former top official's wife and sister sent him air kisses through the glass separating them as he sat in the dock.
Earlier in the trial, Montgomery had asked the judge to show "compassion" for her client, asking for his sentence to be suspended, meaning he would not have to serve any time if he did not commit another offence within a certain period.
Montgomery also said the "ordeal" of the trial had taken a considerable toll on Tsang's physical and mental health.
She pointed to the over 40 letters written in support of Tsang from both his political allies and enemies, including statements from chief executive hopefuls Carrie Lam Cheng Yuet-ngor and John Tsang Chun-wah.
"Mr Tsang must now serve the rest of his life out with the knowledge that his reputation has been ruined and his legacy shattered," she said during Monday's mitigation hearing.
After a high-profile six-week trial, the jury found Tsang had failed to disclose a conflict of interest when he approved three applications from radio broadcaster Wave Media between 2010 and 2012, including a request for a digital broadcast licence.
At the time, Tsang was in negotiations with property tycoon Bill Wong Cho-bau over a luxury Shenzhen penthouse where he intended to retire. Wong was also a 20 per cent shareholder of the radio station
During the trial, the prosecution said Tsang had "abused the system" by intentionally keeping the property a secret from the Executive Council while they were discussing the applications despite rules requiring executive councillors to declare any conflicts of interest.
Tsang's position was "hopelessly compromised" and his "personal loyalties divided" as he continued to make decisions in favour of Wave Media despite his connection to one of its main shareholders, prosecution lawyer David Perry QC said.
"It appeared to the outside world as if he was taking decisions impartially and at arm's-length from those who were to benefit commercially from his decision making," Perry said.
"He should have disclosed his relationship ... instead he suppressed the information, he concealed it."
The former chief executive also faces a retrial for the charge of accepting an advantage while he was chief executive.
Despite deliberating for 20 hours, the jury were unable to reach a verdict on that count, which alleged that Tsang received HK$3.35 million worth of renovations on a Shenzhen apartment as a bribe for approving the Wave Media application
But the jury found Tsang not guilty of another charge of misconduct, which related to suggesting interior designer Barrie Ho Chow-lai for an honour at the time Ho was redesigning the three-storey apartment.
Tsang did not reveal his connection to Ho, but the jury found that this did not constitute misconduct in public office.