Teenaged Ivanka Trump flashed a hot dog seller outside her school, book claims

Ivanka Trump once flashed the hot dog seller who set up his cart over the road from her $44,000-a-year private school, according to a new book.

The daughter of President Donald Trump bared her breasts from a window of the exclusive Chapin school in Manhattan when she was in eighth grade.

The incident became known as a ‘scandale’ but her teachers were not bothered – and were angrier when she lied to them to skip school and work on her modeling portfolio.

Former schoolmates at the all-girls school revealed the prank in a new book which says that Ivanka was a ‘relatively normal teenager’ before she began to carefully manage her public image.

In Born Trump: Inside America’s First Family, author Emily Jane Fox also claims that Ivanka was once forced to do a drug test after attending a raucous party that got out of control. She passed the test.

The incident at Chapin (pictured) became known as a ‘scandale’, but Ivanka did not get in trouble. Her teachers were more concerned about her skipping class for modeling gigs

And, Fox goes on, when Ivanka was in her sophomore year, Ivanka learned how to give a guy oral sex from a friend who showed her on a banana.

The author says that Ivanka’s clique in high school called themselves the ‘Funny Pink Bunnies Club’, though everyone else called them the Lindseys because everyone apart from Ivanka was called Lindsey.

When Ivanka attended Wharton college she would sneak out at 9am from her statistics class to smoke two cigarettes – one after the other – while wearing full makeup and a Burberry trench coat.

Fox’s colorful portrait of Ivanka in Born Trump purports to give private glimpses of a woman who, along with her brothers Don Jr and Eric, grew up under an intense media spotlight with a demanding and remote billionaire father.

Fox says that Ivanka has her father’s ‘self promotional ease without all the brash’ and that the ‘narcissism is hereditary, though muted in its inheritance’.

According to Fox,  watching her parents’ divorce play out in the tabloids when she was a pre-teen gave Ivanka an appetite for carefully controlling everything about her life.

Fox writes: ‘The problem with this branding is that it leaves out one whole side of Ivanka – the realer one.

‘Sometimes, when she lets herself be herself, Ivanka reveals herself as a much more nuanced, relatable, aspirational person than the version of herself she’s crafted.’

Nowhere is that more true than her time at school where her guard was down and she engaged in the kind of high-jinks she would not even dream of now.

Her most high-spirited moment was when she and a friend flashed the ‘kind older man’ who had set up his hot dog stand over the road from Chapin, which counts Jackie Kennedy among its alumni.

In Born Trump: Inside America’s First Family, author Emily Jane Fox peels back the curtain of a woman who, along with her brothers Don Jr and Eric, grew up under an intense media spotlight with a demanding and remote billionaire father. Ivanka is pictured aged 14 in 1995 with her father and Trump’s then-wife Marla Maples

According to Fox, Ivanka was in one of the classrooms facing the hot dog vendor one day when, one a whim, she and her friend lifted up their tops and flashed their breasts at the man.

The school authorities found out but Ivanka was not kicked out.

What seems to have caused her to leave was her modeling career, and she enraged her teachers by going to Mar-a-Lago, her father’s Florida estate, to do some photo shoots and then not telling the truth about why she was absent.

Fox suggests that Ivanka left Chapin under a mutual agreement between her and the school and enrolled at Choate, a $58,000-a-year boarding school in Wallingford, Connecticut.

There she was given a special dispensation to skip school for modeling gigs, but she did not slack off.

Fox writes that she faxed in her school assignments and always did the reading, which was more than some of her schoolmates.

Friends recalled how in school Ivanka would ‘strut down the path between buildings’ arm in arm with her girlfriends as if it was a ‘runway’.

Because of her long legs she was taller than most other people and people saw her as ‘out of their world and kind of untouchable’.

And reminders of her privilege were never far away; at the age of 16 when Ivanka was asked to model a vacuum for a shoot, she had to ask how it worked.

When Ivanka was in school her relationship with her father appears to have remained distant.

Fox suggests that Ivanka left Chapin under a mutual agreement between her and the school and enrolled at Choate (pictured), a $58,000-a-year boarding school in Wallingford, Connecticut

At Choate Ivanka was given a special dispensation to skip school for modeling gigs, but she did not slack off. Fox writes that she faxed in her school assignments and always did the reading, which was more than some of her schoolmates. Ivanka is pictured above at modeling gigs in 1995 (left) and 1999 (right)

Donald did not call her much preferred to send her newspaper clippings about himself or her with notes in Sharpie down the side

Fox writes that when Ivanka was a teenager, her father said she should get breast implants to help her modeling career.

He relented when his sister Maryanne frantically called him and said it would ‘ruin her’.

In Born Trump: Inside America’s First Family, author Emily Jane Fox gives insight into the Trump family’s upbringings 

A friend confronted Donald about it and he denied Ivanka was getting implants, but at the end of the call he asked: ‘Why not, though?’

Ivanka’s most serious brush with her school authorities was at Choate, when Charles Timlin, her English teacher, invited her and some other students to a party at his house.

After Ivanka had left, the party was shut down and the now-first daughter had to be drug tested. She passed but was put on restriction for a few weeks, which was similar to detention.

After the episode there were rumors that her father may have pulled some strings to get her out of trouble because other students who attended the party were suspended or expelled.

Other rumors about Ivanka persisted throughout her time at Choate as well. One was that her father wanted the school to build a helipad so she could fly home to New York on weekends.

Another rumor was that her father hired a limousine to bring her her favorite takeout food from New York, a two-hour drive away.

And when Ivanka attended Wharton college at University of Pennsylvania (pictured) she would sneak out at 9am from her statistics class to smoke two cigarettes one after the other while wearing full makeup and a Burberry trench coat

Donald was notoriously stingy and did not donate anything to the school’s annual book sale because he thought the fees were high enough – some even think he did not pay Ivanka’s full bill for her tuition.

There were also rumors that Ivanka did drugs, particularly cocaine, though she has always strongly denied the claims.

One friend who says he ‘partook’ with Ivanka when she was in her 20s said that she was hanging out with a ‘very rich, very social crew’ at the time.

Ivanka did raise eyebrows in 2012 however when she smoked pot with her friends at the wedding of Natalie Portman and Benjamin Millepied.

Ivanka’s love life in school was sporadic and her prom date was a Canadian jock who trod on her feet so many times as they danced that she had to visit the nurse’s office for pain relief, the book says. 

During a brief stint at Georgetown University, she dated Greg Hersch and they shared his off-campus apartment where they got a yellow Labrador called Tyler.

Ivanka met her future husband, Jared Kushner, in 2007 at a networking lunch arranged by one of her father’s business partners.

The thinking was that Kushner’s background in real estate could be useful for Ivanka, who by now was running her own clothing and lifestyle brand.

Fox writes that the pair hit it off because they are very similar and come from very similar family backgrounds.

Ivanka met her future husband, Jared Kushner, in 2007 at a networking lunch arranged by one of her father’s business partners. The couple are pictured above together in 2007

Fox writes that Ivanka and Kushner hit it off because they are very similar and come from very similar family backgrounds. Kushner is pictured above with his parents, Charles and Barbara Kushner in 2007

She writes: ‘Perhaps the deepest similarity is their ability to compartmentalize. Both know the truth about their fathers – a blow hard philanderer on one side (Trump) and a brutalizing convicted felon on the other (Kushner) – have spent their lives trying to prove themselves and pledge their loyalty to those fathers anyway.

‘Ivanka and Jared watched their dads tear apart their families and turn their backs on everyone.

‘They vowed never to do that to each other or back to their fathers or to the family they would create together.’

After the first lunch Kushner asked Ivanka out again, and she told a friend: ‘Oh my god. Oh my god. Oh my god’, and things became heated soon after.

The only hiccup was a brief breakup in 2008 that left Ivanka ‘devastated’.

They got back together thanks to Wendi Deng, the former wife of Rupert Murdoch, who knew them both and without their knowledge invited them to spend a weekend on the Murdoch private yacht.

Fox writes that Kushner and Ivanka have taken to playing Cupid themselves and have set up seven couples who have gone on to get married – she calls it her ‘secret talent’.

‘Born Trump’ also delves into the past of Ivanka’s brother Don Jr and Fox says that when he was at the University of Pennsylvania he was a boozy jock.

Fox described Don Jr as a was a ‘mix of alcohol and entitlement and raging testosterone’ who would constantly tell people on campus: ‘You don’t know who you’re dealing with.’

Fox described Don Jr as a was a ‘mix of alcohol and entitlement and raging testosterone’. In college, Don Jr became known as ‘Diaper Don’ because he wet himself so often after a night out drinking. He’s pictured above in the early 2000s

One classmate called him ‘undoubtedly an a***hole’. Another said he was ‘classist and messy’.

Don Jr loved the hazing rituals in his fraternity, Phi Gamma Delta, and voluntarily took part in them long after he’d been pledged and hazed in his freshman year, according to the book. 

One of his favorite such rituals was to dress in a barbarian costume and yell as loudly as he could as students walked past.

As Fox notes: ‘This was a task older brothers forced pledges to engage in…Don Jr had already been boned, already shared those humiliations, already paid his dues.

‘He continued to participate, by choice, because, to him, it just seemed like a good time.’

Don Jr became known as ‘Diaper Don’ because he wet himself so often after a night out drinking.

But that wasn’t the only bodily fluid he would be covered in – he often passed out covered in his own vomit, or other people’s vomit, the book says.

Don Jr’s privilege was never far from the surface and during a Spring Break trip to Jamaica he and his Penn buddies went to a bar to watch their basketball team take on a Florida college in the NCAA’s March Madness tournament.

Students from the Florida college happened to be there too and they cheered as their team won 75 to 61.

Fox writes that most of the Penn boys were good-natured about their defeat but Don Jr took things too far.

He got onto a table and tried to get his friends to start a chant which went: ‘That’s all right! That’s okay! You’re gonna work for us someday!’

The Florida college was a state school and, as one Penn student put it: ‘The subtext wasn’t hard for anyone to figure out. And it just came out so easy.’

Fox says that when Don Jr got older he and his father barely spoke, such was Donald’s disappointment in his son, but Don Jr craved his approval and would ‘say anything to make his father happy’.

This turned him into a ‘yapping attack puppy, trailing wherever the senior attack dog with a much bigger bark went’.

Don Jr’s brother Eric Trump became the most like his father and Fox writes that real estate became his obsession.

While at Hill School in Pennsylvania he made the junior varsity squad of the hockey team and during one game he shouted at a player on the opposing team that he was a ‘choad’, an disparaging term for the shape of a penis.

Fox writes that his teammates were ‘stunned, and flipped the name back on him’ and for the rest of his time at the school they called him ‘Choad’ – even in his senior yearbook entry.