Just as Vanessa Trump prepares to become a Trump-no-more, she turns out to be the most interesting one in the family. On Friday, Mother Jones associate editor Patrick Caldwell posted a previously overlooked excerpt from an already-infamous 1998 New York magazine article about Leonardo DiCaprio’s “Pussy Posse” that featured an interesting anecdote about a then Vanessa Haydon.

The 20-year-old model was rumored to be dating the young actor, according to, well, her. The two were seen “nuzzling” at a premiere party for Two Girls and a Guy, and Star magazine published that the actor was a “one-woman man.” Publicist Cindy Guagenti quickly ruined the fantasy and told New York, “He never dated her.”

“At least one person saw DiCaprio walk out of an after-party for a Tony Shafrazi Gallery opening at BondSt,” wrote Nancy Jo Sales. “Just as Haydon was striking up a conversation with a gossip columnist about how happy Leo was to finally be with someone as ‘down to earth’ as she.”

Sales interviewed friends and former classmates of Trump’s at the Dwight School in New York, with one recalling that she was “a total gangster bitch.”

“She was an ill thug,” said a classmate. “She went out with this Latin King for like three years.”

According to Sales, Trump’s classmates voted her “Most Likely to Wind Up on Ricki Lake” for their yearbook. While she never made it to Ricki Lake, her marriage to Donald Trump Jr. in 2005 would take her to Page Six and beyond.

Trump filed for divorce from Don Jr. on Thursday, providing a statement to Page Six. It’s assumed that the couple have a prenuptial agreement since Trump filed for an uncontested proceeding, meaning there will be no back-and-forth over the custody of their five children and assets.

Page Six spoke to Nancy Chemtob, an attorney unassociated with the Trumps’ divorce proceedings, who speculated that Vanessa Trump timed the filing so it could come before the Robert Mueller investigation potentially put her husband’s assets in danger. Planned out like a true ill thug.