Now, his transgender former nanny has given up her tight, flowery dresses, her brocade vest and her bras, and is living in fear on Indonesia's streets.
Evie, who was born a man but believes she is really a woman, has endured a lifetime of taunts and beatings because of her identity. She describes how soldiers once shaved her long, black hair to the scalp and smashed out glowing cigarettes onto her hands and arms.
The turning point came when she found a transgender friend's bloated body floating in a backed-up sewage canal two decades ago. She grabbed all her girlie clothes in her arms and stuffed them into two big boxes. Half-used lipstick, powder, eye makeup - she gave them all away.
"I knew in my heart I was a woman, but I didn't want to die like that," says Evie, now 66, her lips trembling slightly as the memories flood back. "So I decided to just accept it. ... I've been living like this, a man, ever since."
Indonesia's attitude toward transgenders is complex.
Nobody knows how many of them live in the sprawling archipelagic nation of 240 million, but activists estimate 7 million. Because Indonesia is home to more Muslims than any other country in the world, the pervasiveness of men who live as women and vice versa often catches newcomers by surprise. They hold the occasional pageant, work as singers or at salons and include well-known celebrity talk show host Dorce Gamalama.
However, societal disdain still runs deep - when transgenders act in TV comedies, they are invariably the brunt of the joke. They have taken a much lower profile in recent years, following a series of attacks by Muslim hard-liners. And the country's highest Islamic body has decreed that they are required to live as they were born because each gender has obligations to fulfill, such as reproduction.
"They must learn to accept their nature," says Ichwan Syam, a prominent Muslim cleric at the influential Indonesian Ulema Council. "If they are not willing to cure themselves medically and religiously" they have "to accept their fate to be ridiculed and harassed."
Many transgenders turn to prostitution because jobs are hard to find and because they want to live according to what they believe is their true gender. In doing so, they put themselves at risk of contracting AIDS and other sexually transmitted diseases.
Some, like Evie, have decided it's better to hide their feelings. Others are pushing back. Last month, a 50-year-old Indonesian transvestite applied to be the next leader of the national human rights commission, showing up in a borrowed luxury vehicle with paparazzi cameras flashing as she stepped out.
"I'm too ugly to be a prostitute," Yuli Retoblaut said, chuckling. "But I can be their bodyguard."
The threat of violence is very real: Indonesia's National Commission for Human Rights receives about 1,000 reports of abuses per year, ranging from murder and rape to the disruption to group activities. Worldwide, at least one person is killed every other day, according to the Trans Murder Monitoring Project, which collects homicide reports.
Evie says she chose her current name because she thought it sounded sweet. But she adds, as she pulls out her national identification card, her official name is Turdi and gender male. Several longtime residents of Obama's old Menteng neighbourhood confirmed that Turdi had worked there as his nanny for two years, also caring for his baby sister Maya. When asked about the nanny, the White House had no comment.
Evie, who like many Indonesians goes by a single name, now lives in a closet-sized hovel in a tightly packed slum in an eastern corner of Jakarta, collecting and scrubbing dirty laundry to pay for food. She wears baggy blue jeans and a white T-shirt advertising a tranquil beach resort far away in a place she's never been. She speaks softly, politely, and a deep worry line is etched between her eyes.
As a child, Evie was often beaten by a father who couldn't stand having such a "sissy" for a son.
"He wanted me to act like a boy, even though I didn't feel it in my soul," she says.
Teased and bullied, she dropped out of school after the third grade and decided to learn how to cook.
As it turned out, she was pretty good at it, making her way into the kitchens of several high-ranking officials by the time she was a teenager, she recalls with a smile and a wink. And so it was, at a cocktail party in 1969, that she met Ann Dunham, Barack Obama's mother, who had arrived in the country two years earlier after marrying her second husband, Indonesian Lolo Soetoro.
Dunham was so impressed by Evie's beef steak and fried rice that she offered her a job in the family home. It didn't take long before Evie also was 8-year-old Barry's caretaker, playing with him and bringing him to and from school.
Neighbours recalled that they often saw Evie leave the house in the evening fully made up and dressed in drag. But she says it's doubtful Barry ever knew.
"He was so young," says Evie. "And I never let him see me wearing women's clothes. But he did see me trying on his mother's lipstick, sometimes. That used to really crack him up."
When the family left in the early 1970s, things started going downhill. She moved in with a boyfriend. That relationship ended three years later, and she became a sex worker.
"I tried to get a job as a maid, but no-one would hire me," says Evie. "I needed money to buy food, get a place to stay."
It was a cat-and-mouse game with security guards and - because the country was still under the dictatorship of Gen. Suharto - soldiers. They often rounded up "banshees" or "warias," as they are known locally, loaded them into trucks, and brought them to a field where they were kicked, hit and otherwise abused.
The raid that changed everything came in 1985. She and her friends scattered into dark alleys to escape the swinging batons. One particularly beautiful girl, Susi, jumped into a canal strewn with garbage.
When things quieted, those who ran went back to look for her.
"We searched all night," says Evie, who is still haunted by the memory of her friend's face. "Finally ... we found her. It was horrible. Her body swollen, face bashed in."
Today Evie seeks solace in religion, going regularly to the mosque and praying five times a day. She says she's just waiting to die.
"I don't have a future any more."
She says she didn't know the boy she helped raise won the 2008 US presidential election until she saw a picture of the family in local newspapers and on TV. She blurted out that she knew him.
"I couldn't believe my eyes," she says, breaking into a huge grin.
Her friends at first laughed and thought she was crazy, but those who live in the family's old neighbourhood say it's true.
"Many neighbours would remember Turdi ... she was popular here at that time," says Rudy Yara, who still lives across the street from Obama's former house. "She was a nice person and was always patient and caring in keeping young Barry."
Evie hopes her former charge will use his power to fight for people like her. Obama named Amanda Simpson, the first openly transgender appointee, as a senior technical adviser in the Commerce Department in 2010.
For Evie, who's now just trying to earn enough to survive each day on Jakarta's streets, the election victory itself was enough to give her a reason - for the first time in a long time - to feel proud.
"Now when people call me scum," she says, "I can just say: 'But I was the nanny for the President of the United States!'"
