Published: 2021-09-02 10:26:22 BdST
The premier sued writer Rubaashini Shunmuganathan and editor Xu Yuan Chen, also known as Terry Xu, over an August 2019 article on The Online Citizen (TOC) that included references to a Lee family disagreement about what to do with the property.
Judge Audrey Lim said the article "impugned Lee's reputation and character" by alleging he was dishonest.
"This struck at the heart of Lee's personal integrity and could severely undermine his credibility, not just personally but also as the prime minister, and call into question his fitness to govern with integrity," Lim said in a written judgement.
Xu, a Singaporean, and Malaysian Rubaashini were ordered to pay Lee S$210,000 and S$160,000 respectively. The judge, however, asked them to jointly pay S$160,000 in damages, as the lawsuits concerned the same defamatory article.
Rubaashini did not immediately respond to a request for comment. Xu on his social media said he was disappointed with the judgement and was assessing next steps he could take, such as an appeal.
Xu has also set up crowdfunding for the case, a move taken separately in April by an activist and a financial advisor, both of whom Lee had successfully sued for defamation.
Lee appeared in court in the case involving TOC in May, during which he said "sensational allegations" had been made.
His press secretary in a statement on Wednesday said the damages awarded would be donated to charity.
Senior figures in the ruling People's Action Party, including Lee Kuan Yew, have also sued foreign media and political opponents for defamation, calling it defence of their reputations.
Some activists, including the New York-based Human Rights Watch, say such moves are stifling freedom of speech and political opposition.