The Truth Behind Vanessa Trump’s Relationship With a Saudi Prince (and the Alleged 9/11 Connection No One Expected)

It seemed like their 12-year marriage was going strong, but after Donald Trump Jr.’s cheating scandal, it all fell apart. Vanessa Trump filed for divorce against Don Jr. back in March. And now, the two are working on separating amicably for the good of their five children.

The drama doesn’t end there, of course. As Don Jr.’s troubles heat up with the media, so do Vanessa’s. And it turns out she may have had a very serious relationship with a Saudi Prince. There’s even speculation his father had something to do with the 9/11 attacks, too (page 5).

1. Vanessa Trump has a wild dating history we can barely keep up with

Donald Trump Jr. and Vanessa Trump

Vanessa has dated several high-profile men. | Brian Ach/Getty Images for Make-A-Wish Metro New York

Vanessa and Donald Trump Jr.’s first encounter was anything but romantic. Elite Daily explains Don Jr.’s father, the infamous Donald Trump, introduced his son to Vanessa at a fashion show in 2003. He didn’t only do this once, either. Vanessa was introduced to Don Jr. twice in about five minutes.

They managed to hit it off eventually, fall in love, and then decide to marry. But as for Vanessa, that’s far from the most bizarre dating story she has. From gang members to celebrities, it gets a whole lot crazier than Don Jr.

Next: Vanessa may not come from a squeaky-clean past.

2. She allegedly dated someone from a street gang when she was in high school

She ran with a tough crowd in high school. | William West/Getty Images

Page Six reports back in her high school days Vanessa Trump went to prom with Valentin Rivera, a member of the dangerous Latin Kings gang. Valentin even spoke to the publication and said Vanessa would help him drop marijuana off to his friends at the time. When she drove him around, she even reportedly had an illegal gun in the trunk.

Her friends started to fear her boyfriend. As Valentin told Page Six, “If anybody disrespected her in any way, I would physically put my hands on them.”

Next: Did Vanessa really cheat on her gang member boyfriend with this celeb?

3. Valentin Rivera says Vanessa Trump cheated on him — with Leonardo DiCaprio

Left: In 1998, Leonardo DiCaprio was quite the bachelor. | Brenda Chase/Getty Images, Right: She was liked to him back then. | William West/Getty Images

According to Valentin Rivera, he and Vanessa were deeply in love and even discussed having children, Page Six reports. But that all came crashing down when Valentin saw in the New York Post that Vanessa had allegedly moved on to be with Leonardo DiCaprio. In 1998, Page Six revealed that Vanessa and her new celebrity boyfriend were seen “holding hands, kissing and cuddling into the wee hours in a dimly lit corner.”

Valentin was heartbroken and humiliated by the news. But despite it all, he wishes Vanessa the best.

Next: This is when Vanessa’s dating history really gets interesting.

4. Vanessa met a Saudi Prince, and they quickly fell in love

american flags flying in front of the world trade center on 9/11/01

The relationship abruptly ended on 9/11. | Craig Allen/Getty Images

Her other romances caused quite a stir, but this one really takes the cake. Page Six says sources claim Vanessa was involved with Prince Khalid bin Bandar bin Sultan Al Saud from Saudi Arabia. The sources also say the two dated from 1998 to 2001 and even lived together. “They were inseparable,” they claimed. And the two of them may have even planned to wed.

This relationship ended abruptly, however, as the prince allegedly ditched Vanessa on 9/11 and flew back to Saudi Arabia days later.

Next: This connection to 9/11 is wild.  

5. Prince Khalid’s father was accused of having indirect ties to the 9/11 attacks

Was Prince Bandar bin Sultan bin Abdul Aziz al-Saud (with Vladimir Putin) involved with the 9/11 attacks? | ALEXEY NIKOLSKY/AFP/Getty Images

You may not have realized that the prince’s father was Saudi Arabia’s ambassador to the U.S. for over 20 years, Vanity Fair notes. Bandar bin Sultan Al Saud also had close ties with the Bush family. But directly after 9/11, many questioned whether the elder Al Saud had any connection to the attacks.

According to the publication, phone numbers indirectly linked to Al Saud were found in an al-Qaeda recruiter’s phone in Pakistan. In 2005, a CIA report said there was no evidence that he was involved, however.

Next: Were Vanessa and the prince meant to be after all?

6. One source says Prince Khalid treated Vanessa better than Donald Trump Jr. did

Donald Trump Jr. and Vanessa Trump

Trump reportedly didn’t treat her well. | Robyn Beck/AFP/Getty Images

There’s plenty of controversy regarding how Don Jr. treated Vanessa through their years of marriage. And interestingly enough, one source told Page Six that the Saudi prince “treated her as if she was his queen. It was the complete opposite from Don Jr. They were together 24/7. They were a real couple.”

Not every source agrees with this assessment of their relationship, however. Another individual told Page Six that the two “never lived together and were not planning to get married.”

Next: Don Jr. is ready to give up on Vanessa for good.

7. Don Jr. has already moved on to a new woman

Left: Donald Trump Jr. is ready to move on after his seperation with Vanessa Trump. | Mike Stobe/Getty Images, Right: Kimberly Guilfoyle seems to be his new flame. | Jamie McCarthy/Getty Images

Vanessa has an intense dating history, but it seems Don Jr. is the one making waves with his most recent choice in women. Aside from the Aubrey O’Day scandal, the president’s son is now reportedly dating Fox News host Kimberly Guilfoyle, People reports.

The publication notes they’ve reportedly been dating for a few weeks now. And this is just two months after Vanessa filed for divorce. As one source says, “While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly’s company.”

Next: Here’s where Don Jr. and Vanessa currently stand.

8. Are Don Jr. and Vanessa on good terms now?

Donald Trump Jr.’s mother’s day tweet. | Donald Trump Jr. via Twitter

Don Jr. and Vanessa didn’t seem to leave things on good terms — especially since news broke of Don Jr.’s affair. But all in all, it seems the soon-to-be-divorced couple is trying to work things out amicably for the good of their five children. Don Jr. even tweeted a nice note about Vanessa on Mother’s Day, calling her “the best mom in the world.”

It seems money may make the divorce proceedings relatively ugly, however. In Touch Weekly reports Don Jr. demanded Vanessa reveal her net worth while they were in court after word got out that her family may have inherited a lot of money. Hopefully, they can settle things without the media getting too involved.

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