The Stunning Transformation Of Vanessa Trump

Vanessa Trump, ex-wife of Donald Trump Jr. and the mother of his five children, has largely flown under the radar compared to other members of the Trump family. After all, between President Donald Trump's three marriages, two divorces, and the kids he has with each of his three wives, not to mention their spouses and children, keeping track of who's who in the first family can be a pretty daunting task. 


While Vanessa isn't one of the better known members of the Trump family, that seems to be by design. Much of her life before she became involved with the younger Trump seems to be shrouded in speculation, and she hasn't led a very public life since her marriage. What we do know about Vanessa, though, is that she has changed quite a bit over the decades, transforming from a young model to an heiress with some pretty strong ties to the White House.

Vanessa Trump enjoyed a privileged upbringing

Marrying into the Trump family was not Vanessa Trump's introduction to the lifestyle of the well-to-do. She might not have grown up in the White House, but her upbringing was still a pretty pampered one. Born Vanessa Haydon, she grew up in luxury on Manhattan's Upper East Side where she and her family lived in a townhouse. The young Vanessa attended the pricey Dwight School across town which, as of this writing, costs a whopping $48,620 per year. Vanessa's mother, Bonnie Haydon, ran a modeling agency while her father, Charles Haydon, was a celebrity attorney whose famous clients included iconic figures like actress Marilyn Monroe. 


Vanessa Trump and her sister, Veronika, had a nanny to take care of them while their high-profile parents went to work. Trump told The New York Times that, as a child, she would regularly attend "crazy parties" with her nanny where she rubbed shoulders with models

Vanessa Trump's high school years were allegedly pretty wild

According to former classmates, Vanessa Trump was rather wild in her youth. Her high school sweetheart was reportedly gang member Valentin Rivera who has served several prison stints for a range of crimes including assault and negligent homicide. In an interview with Page Six, Rivera said that the teenage Trump (then Haydon) helped him deliver weed and that they even stayed together when he was sent to a maximum security juvenile prison. "She was heartbroken that I was being taken away," said Rivera. "The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things. She only came to visit me twice because her mother forbid her from coming to visit me."


Rivera claims Trump was his "first love," but he doesn't begrudge her moving on. "I'm happy for her that she has five beautiful children and she's doing well," he said.

While Trump hasn't publicly denied the alleged relationship, a representative commented, "Vanessa is a devoted mother of five amazing children. This is nothing more than an attempt to sensationalize over 20-year-old 'stories' from high school for clickbait."

Did Vanessa Trump date Leonardo DiCaprio?

Surprisingly, Valentin Rivera says that it wasn't his gang activity and his trouble with the law that ended his relationship with Vanessa Trump. Instead, he said that he broke up with her after the New York Post reported that she had been seen on a date with film star Leonardo DiCaprio. "DiCaprio's luscious love is 20-year-old fashion model Vanessa Haydon," read the story, which ran on May 1, 1998 and was reprinted by Page Six as part of their 2018 interview with Rivera. "The passionate pair have been inseparable over the past two weeks." The original reported continued, "They 'tried to keep a tight lid on their budding romance' — but it all spilled out during a private party in a trendy SoHo loft last week ... The couple could be seen holding hands, kissing and cuddling into the wee hours in a dimly lit corner."


The relationship was never officially confirmed, and New York Magazine suggested that Trump had started the rumor herself, but it was circulated enough that it meant the end of the alleged relationship between the then-future Trump and Rivera.

Vanessa Trump could have been a princess

After the rumored relationship between Vanessa Trump and Valentin Rivera ended, Vanessa was said to have moved on to Prince Khalid bin Bandar bin Sultan Al Saud. An anonymous source told Page Six that they planned to marry and were living together, but the prince broke up with her and returned home to Saudi Arabia following the September 11 attacks. While there was no evidence linking him or his father, Bandar bin Sultan Al Saud, to the attacks, the elder Al Saud was suspected of being linked to al Qaeda. The elder Al Saud had previously served as Saudi Arabia's ambassador to the United States from 1983 to 2005.


"Bandar treated her as if she was his queen," said the source. "It was the complete opposite from Don [Trump] Jr. They were together 24/7. They were a real couple."

Sources close to the Trump family, however, say that the relationship was nowhere near as serious as reported and that Vanessa and the prince simply dated but never lived together and didn't have plans to marry.

Like other Trumps, Vanessa Trump was a model

Like many of the women in the Trump family, Vanessa Trump is a former model. It seems that Donald Trump Jr. has similar tastes to his father, whose three wives — Ivana Trump, Marla Maples, and Melania Trump — are all former models. The president's daughters have also continued what seems to be a Trump tradition. Ivanka Trump was formerly signed to Elite Model Management Corp's celebrity division while her younger half-sister, Tiffany Trump, has been occasionally spotted on the runway.


While Vanessa's modeling past isn't as widely publicized as the First Lady's, she has extensive experience posing for the cameras. While the fact that her mother ran a modeling agency may have helped ease her way into the industry, Vanessa's good looks and long legs ensured that she found steady work. She began modeling as a child and was signed to Wilhelmina, as reported the New York Times in 2006.

Donald Trump Sr. played matchmaker for his son and Vanessa Trump

How does a model and socialite who has reportedly dated a gang member and a prince end up with the son of a businessman? By being set up by the guy's dad. Donald Trump was apparently eager to set up his son, Donald Trump Jr., with the model. "I'm at this fashion show," Vanessa Trump told The New York Times of meeting the Trumps in 2003. "Donald Trump comes up to me with his son: 'Hi, I'm Donald Trump. I wanted to introduce you to my son Donald Trump Jr.'"


After an awkward conversation, the three went back to the fashion show. At intermission, the older Trump again introduced his son to Vanessa, apparently forgetting that he'd already made the introduction. Vanessa reportedly wasn't impressed at first, and it wasn't until a few weeks later, after again being introduced by a mutual friend, that she clicked with Donald Jr. "We talked for an hour," she said. From there, the romance unfolded.

Vanessa Trump's marriage proposal was a publicity stunt

While it seems that Vanessa Trump is the kind of woman that Donald Trump wanted his son to be with, he wasn't always supportive of the relationship, or at least he wasn't supportive of his son's actions. Once Vanessa and Donald Jr. got together, it seemed like things were going smoothly until their not-so-romantic engagement. Donald Jr. proposed with a $100,000 ring in 2004. The New York Post reported at the time that Donald Jr. got the ring for free in exchange for a public proposal outside New Jersey jewelry store Bailey, Banks & Biddle. The proposal brought in publicity for the store, but many thought that it was tacky. Fortunately, Vanessa did get a more romantic proposal a couple months earlier at the couple's home. 


Donald Jr.'s dad later went on Larry King Live and expressed his disapproval. "You have a name that is hot as a pistol, you have to be very careful with things like this," said the then-future president on the show (via The New York Times).

Vanessa Trump's Mar-a-Lago wedding

Her public engagement might not have been the most glamorous event, but at least Vanessa Trump wed in style, as reported by People. She and Donald Trump Jr. tied the knot at his dad's Mar-a-Lago resort in Florida, the estate that the president would later unofficially dub "the southern White House" because of the amount of time he spends there. The extravagant ceremony took place in November 2005, less than a year after the then-future president married his third wife, Melania, at Mar-a-Lago. Vanessa and her husband were both 27 years old.


The nuptials took place poolside, and the bride wore a dress she had designed herself. The ceremony was on the modest side for a Trump event, although the wedding took place in front of 370 guests. Judge Maryanne Trump Barry, the groom's aunt, officiated the wedding, making the wedding a true Trump affair. It was a seemingly fairy tale wedding and one that would mark a turning point in Vanessa's life. 

Ivanka Trump looks up to Vanessa Trump

She isn't one of the better known members of the extensive Trump clan, but it seems that, at least within the family itself, Vanessa Trump is one of the most respected. Donald Trump's eldest daughter, Ivanka Trump, has not been reserved in expressing the admiration she has for Vanessa, or at least she wasn't before Vanessa left Ivanka's brother. "My sister-in-law Vanessa is a machine," Ivanka told People in 2016. "She can take all of [my children] and not even notice. She has five children and she's Wonder Woman to me." She continued, "She can be taking care of them all simultaneously, each pulling on her and have direct meaningful connections with each of them at one time. It's remarkable."


Ivanka added that Vanessa is "an amazing mother and really an inspiration to me." The president's daughter also said that Vanessa is one of the people that she goes to for parenting advice. 

Anonymous sources claim Vanessa Trump's marriage was rocky for years

The Trump divorce might have come as a surprise to many, but those who are closest to the family claimed that the relationship between Vanessa Trump and Donald Trump Jr. had been rocky for quite some time. "He gives her very little help and has been keeping her on a tight budget," one anonymous source told Page Six in 2018. "She doesn't live a lavish life and can very rarely pick up a check at dinner."


While Vanessa's spokesperson denied the rumors that Donald Jr. was tightfisted and treated his wife "like a second-class citizen," there were problems in the relationship beyond money. According to Us Weekly, Donald Jr. was involved in an affair with Danity Kane singer Aubrey O'Day from the end of 2011 to March 2012, allegedly ending it only after Vanessa found out about it. While they reconciled, the alleged affair reportedly took a toll on their marriage and might have been one of the contributors to their eventual divorce. 

Melania Trump allegedly warned Vanessa Trump that the family's men are power-hungry

Sources claim that Vanessa Trump was warned about Donald Trump Jr. more than once. "People were telling her not to marry him before the wedding," one insider told Page Six. While she went through with the wedding, it seems that people were still skeptical about the couple.


The First Lady herself, Melania Trump, also reportedly warned her stepdaughter-in-law about what the Trump men are really like. "Melania told her, 'The Trump men are one and the same — vain and ­power-hungry,'" an anonymous source told Us Weekly. Vanessa had allegedly gone to her mother-in-law for relationship advice, prompting the warning. It would seem that Melania doesn't have much confidence in her stepson. She allegedly warned Vanessa to tread lightly, saying that "she could do nothing to change that and offering her husband an ultimatum would be a huge mistake because he would choose his thirst for power like his dad."

Being close to the president made Vanessa Trump a target

Being part of the first family can take quite a toll even on extended members of the family. Things got scary for Vanessa Trump in February 2018, after she opened an envelope addressed to her husband, Donald Trump Jr., that was filled with a powdery white substance, as reported by the New York Post. While the substance turned out to be cornstarch, Vanessa was rushed to the hospital in case the then-unknown substance ended up being toxic. The envelope turned out to be a prank, but it left Vanessa terrified. 


"It was a cowardly act against a mother," Vanessa later told Axios. "And even today, every time I open the mail, I feel the same fear in my heart as I did that day. These recent acts are the acts of a coward and nothing more than terrorism, pure and simple. No one, regardless of political party or ideology, should ever have to go through what I went through."

Vanessa Trump has been focusing on motherhood

Vanessa Trump seems to have been laying pretty low since her highly publicized divorce from Donald Trump Jr. was finalized in February 2019. For now, it looks like she's enjoying being on her own and devoting herself to her kids. While she's on social media, her Twitter account doesn't reveal too many personal details, although it is filled with photos of her kids. "I'm a mother of 5 amazing kids," reads Vanessa's Twitter bio. "My children are my life!"


Vanessa regularly posts pictures of her adorable kids. "Happy 5th birthday to my princess Chloe Sophia!" she captioned a photo collage of her daughter in June 2019. "You always make everyone smile! May all your dreams come true! We all love you!"

Her infrequent posts are mostly centered around her kids and her love for them. Vanessa doesn't seem to be too into divulging the details of her personal life, but is making it clear that she's a devoted and loving mother.

Vanessa Trump is still tight with the Trump family

Even though she's no longer legally part of the Trump family, Vanessa Trump still maintains her bond with them. Her kids are still Trumps by blood, after all, and it seems that Vanessa is doing her best to stay tight with her former in-laws. When she's not tweeting about her kids, she's posting tributes to the family, including a happy birthday post to "grandpa," aka President Donald Trump in June 2019. 


The president's former daughter-in-law was also seen outside the home of his older daughter, Ivanka Trump, and her husband, Jared Kushner, dropping off some of her children in September 2018, as reported by Vanity Fair. While it isn't clear if Vanessa and Ivanka are as close as they were before the split, it's apparent that they aren't letting the end of Vanessa's marriage keep their children apart. While Vanessa may no longer legally be a member of the Trump family, she doesn't seem to be prepared to completely cut ties with the presidential clan, at least for now.

Vanessa Trump is an heiress in her own right

While there were rumors that Vanessa Trump was leaving Donald Trump Jr. because of his tightfisted ways, the former model isn't exactly hurting for cash. While her mother is still alive, Vanessa inherited a not-so-small fortune from her father, Charles Haydon, who passed away in 2005. Haydon, in addition to being a successful attorney, also made some pretty savvy investments that paid dividends even after his death. Page Six reported that Haydon owned 30 percent of Rao's Specialty Foods which manufactures sauces, olive oils, and dressings that are sold internationally.


The company was sold for roughly $415 million in 2017, leaving Vanessa and her family with a sizable windfall. According to People, the money would have been untouchable by Donald Jr. in the divorce proceedings, as it was part of an inheritance. The fortune ensures that Vanessa will be able to be financially independent, with or without her ex-husband.