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.

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."

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.

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.

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. 

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. 

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."

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.