Ferrari driver Shi Ka Yee, 73, charged with a string of offences, was aggressive only towards men because they reminded the woman of the way her former husband had treated her.
A private psychiatrist made this assessment in a report that Shi's lawyers submitted as new evidence in an appeal to the High Court. They are seeking a mandatory treatment order (MTO) for her instead of jail.
Justice Chan Seng Onn yesterday questioned whether an MTO would make a difference, noting that Shi still committed offences despite having been on medication for depression since 2009.
Still, the judge called for a report from an Institute of Mental Health (IMH) psychiatrist to assess if Shi was suitable for an MTO.
He directed that the report was to address why past treatment has not prevented her from committing offences.
Shi's lawyers, Senior Counsel N. Sreenivasan and Mr S. Balamurugan, are appealing against the sentence of four weeks' jail and a six-month driving ban handed down by a district judge in March. This was for punching motorist Raphael Chong Yen Ping in 2014.
The lawyers said their client will be seeking an MTO for her other charges as well, on the grounds that her persistent depressive disorder contributed to the stark change in her behaviour between 2014 and last year.
Shi has pleaded guilty to various charges in separate incidents, such as confining a worker in a crane's bucket for pruning a tree on her Astrid Hill property in February 2015 and stopping her car in the middle of Orchard Road in June 2016, causing a jam, after a private bus driver complained she was driving too slowly.
She also faces charges for drink driving and failing to provide a breath sample to a police officer.
The report by private psychiatrist Tommy Tan said Shi's history of aggressive behaviour started late in life.
He added that she became agitated whenever something reminded her of her former husband.
Shi has been seeing Dr Pauline Sim from Mount Elizabeth Medical Centre since 2009 after she found out about her husband's extramarital affair.
According to Shi's daughter, her mother, who had her own design company, was the sole breadwinner for a very long time as her former husband was unemployed for a large part of their marriage.
Deputy Public Prosecutor Wong Kok Weng argued that Shi did not seek an MTO during the trial stage, even though she was aware of the option.
She was trying to get a "second bite of the cherry", he said, noting that the district court had already ruled her depression did not contribute to her assault on Mr Chong.
Mr Sreenivasan said Shi's previous lawyers did not explain sufficiently the significance of an MTO to her. She was also worried about being labelled as an IMH patient and thought that an MTO meant a plea indicating she was mad.