Former shipping tycoon Tong Djoe, 87, was made a bankrupt on Thursday after failing to pay $285,000 over an art deal in which the painting he sold was a fake.
The sum he owes includes the legal costs and interest that the court awarded Hong Kong businessman Lawrence Wong Chun Lam, when he won his suit against Mr Tong for $200,000 in 2010.
Mr Wong filed bankruptcy proceedings last year against Mr Tong, who in the last three years lost another $690,000 in two other lawsuits - one of which involved more fake art.
Mr Tong, a Chinese-Indonesian businessman who was once prominent in the Chinese community here, made millions from Tunas, the shipping and trading firm he founded in 1960. In his heyday, he developed the Tunas Building in Anson Road. The building was sold in 1981 after Tunas' fortunes started to slide and it is now known as Hub Synergy Point.
In 2007, Mr Wong sued him to get back a $200,000 deposit for a painting purportedly by renowned Chinese artist Xu Beihong, and other artworks, after learning that the painting was not authentic.
In December 2010, a district court ruled in his favour. Mr Tong lost his appeal last March.
In 2011, he was ordered by the High Court to refund $300,000 to Dr Cheryl Baumann, chief executive of the Singapore Medical Group. Dr Baumann had paid Mr Tong the money for 19 paintings and a wood carving but later found out some of the artworks were fake.
Last October, the High Court also ordered Mr Tong to pay back a 2 million yuan (S$390,000) loan that he took from Chinese businesswoman Chen Qiling.
Mr Tong, who is in Indonesia, was not available for comment.
In 2002, he was involved in a bitter court battle against some of his children and grandchildren who wanted to sell the family's $4million Namly Crescent home. At the end of this trial, which revealed that he had children from extramarital affairs, he lost his fight to stop the sale of the house.
In 1986, his wife, with whom he had six children, drowned in the pool of the family home.