Trump Jr.’s Wife, Vanessa, Called ‘Ill Thug’ Presumably ‘Planned Out’ Divorce Filing, Claims ‘Vanity Fair’

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Vanessa Trump has filed for divorce from Donald Trump Jr. this week, which Vanity Fair reports is no coincidence. In high school, the mother of five was voted “most likely to be on Rikki Lake,” spent years working as a model, was introduced to her husband by his father, and even reportedly dated Leonardo DiCaprio.

Describing her as “the most interesting on in the family,” what more did the publication report on the former Vanessa Kay Haydon, who was nicknamed “ill thug” in high school?

Vanessa Haydon Trump, who recently filed for divorce from Donnie Jr. after nearly 13 years of marriage, was a model from childhood and originally part of Leonardo DiCaprio’s “p**** posse,” alleges New York Magazine.

Donny’s soon-to-be-ex was reportedly seen “nuzzling” with Leonardo in the late ’90s when the Titanic actor’s career was just beginning to rise.

The pair were reportedly seen at the Two Girls and a Guy premier party at Moomba and at other social events. There were rumors that he had “fallen hard” for one woman, indicating the woman in question was the then-Wilhemena model, Vanessa.

Yet, according to his publicist Cindy Guagenti, who flatly denied any romantic connection, “He never dated her.”

It was reported by New York Magazine that it was Vanessa who planted gossip into the ear of a columnist, claiming that the Blood Diamonds actor found someone “down to earth” and was now a “one-woman man.”

A male friend that hung out and went clubbing with Vanessa in their teens had plenty to say about her, claiming she used to be more of a hard rock chick, wearing “leather and baggy jeans,” but is now “dolled up and ladylike.” They indicated that the future Mrs. Trump was good at playing the game.

“Vanessa played the media really well.”

A female friend revealed that in high school, she was nicknamed the “ill thug,” as she dated “this Latin king,” for several years. This is the same school that voted her “The most likely to wind up on Ricki Lake.”


Vanessa was “awkwardly” introduced to her husband by her future father-in-law, twice, claims Business Insider, and the two married at Mar-a-Lago. The two have three boys and two girls, Donald III, Spencer, Tristan, Chloe, and Kai Madison.

As for the Trump Jr. divorce, Page Six spoke to some legal experts who were not handling the divorce but were experienced in high-profile divorces. The consensus was that Vanessa surely signed an iron-clad prenup as prominent divorce lawyer Michael Stutman explained that prenups are part of the family “DNA.”

“Prenuptial agreements and confidentiality agreements are in the Trump dynasty DNA so I would be surprised if Donald Jr. went into the marriage completely naked.”

They also point out that the divorce was filed on the very same day that special counsel Robert Mueller subpoenaed the president’s family business in order to uncover any connections to Russia.


There is also speculation that she is also maneuvering to legally avoid testifying against Trump Jr. in the Russia probe.

Family lawyer Nancy Chemtob even “speculated” that Vanessa may be filing for divorce now before his considerable financial assets were put at risk.

How considerable? According to Celebrity Net Worth, Donald Trump Jr. is worth a cool $300 million.