She allegedly cheated her friend of about $200,000 in total over a 14-year period by claiming that payments were needed for Mr Lee Kuan Yew.
Dishwasher Tan Hwee Ngo, now 67, allegedly duped petrol station pump attendant, Mr Tan Soy Kiang, into handing over the money between 1999 and 2013.
She was charged in court yesterday with 169 counts of cheating.
However, court papers did not mention if the Mr Lee she had allegedly been referring to was Singapore's late former prime minister.
In June 1999, she allegedly induced Mr Tan, now 72, into withdrawing $53,161.64 of his Central Provident Fund savings by claiming that he had owed monies to the Government that needed to be paid to Mr Lee.
From then on, she allegedly used the same reason to cheat Mr Tan. He is said to have given at least $500 cash every month starting January 2000 to their friend, retired cleaner Boo Sok Hiang, then 69.
Mr Tan's case came to light when his niece, Ms Pamela Lim, returned from Australia in 2013 after living there for 15 years and discovered that her uncle had been giving his money away.
She confronted the alleged scammers the following year before alerting the police.
The New Paper reported in March 2015 that members of the public donated $63,000 to Mr Tan after news about the case broke earlier that year.
Mr Dan Chen, then 28, who works for an international school, had earlier started a campaign on crowd-funding site Indiegogo to raise US$5,000 (S$6,900), which attracted donors from as far as Hong Kong, Australia and the United States. Mr Chen handed Mr Tan a cheque for the $63,000 on March 28, 2015.
Mr Tan, who used to live alone, once held two jobs.
The bachelor worked every morning as a cleaner along Kim Keat Avenue, earning about $1,000 a month.
From 4pm to 10.30pm, he worked as a pump attendant, earning another $1,000 a month.
Ms Lim, 41, told The Straits Times yesterday that he has stopped working as a cleaner since investigations started. The mother-of-three said: "He is now living with me and is doing well. My kids adore him."
Yesterday, Tan Hwee Ngo was offered bail of $20,000. Her son accompanied her to court and told reporters that the past two years have been difficult for his mother.
She is represented by lawyer Mathew Kurian from Regent Law and will be back in court on June 22. For each count of cheating, she can be jailed for up to seven years and fined if convicted.
Madam Boo reportedly died last year. Neighbours were quoted in Shin Min Daily News yesterday as saying that she had a fall around a year ago and was helped back to her house.
She had bruises on her arms and legs, could not walk properly and had to crawl around at home.
"I took care of her over the next few days, giving her porridge and drinks," a neighbour told the Chinese evening daily.
"I suggested asking her son to take her to hospital, but she said not to disturb him at work," said the neighbour.
• Additional reporting by Abigail Ng