Vanessa 'thugs' and kisses
Don Jr. wife’s teen love letters to jailed gangster boyfriend
BEFORE her Sweet 16, Vanessa Trump sent her high-school sweetheart — then a member of a notorious street gang who was just beginning a 16-month prison sentence for assault — a love note saying she dreamed of having children with him.
Page Six has exclusively revealed that despite being a quiet member of America’s first family and the estranged wife of Donald Trump Jr., Vanessa’s first true love was her school sweetheart, Valentin Rivera, a member of the violent Latin Kings street gang.
She dated Rivera for five years beginning when they were just 15, and her letters reveal she couldn’t wait to start a family with him at just 18 years old.
In a note dated Dec. 13, 1993 — packed into an envelope with SWAK (“Sealed With a Kiss”) written on the back — Vanessa wrote, “I miss you a lot, especially since it’s my birthday coming up. And I wish you were here to celebrate with me. But you’ll be out [of prison] for my 18th birthday.”
She added in the note, one of nearly a dozen letters handwritten by Vanessa, sent to Rivera in prison and seen by Page Six, “I can’t wait till that year because a lot’s going to happen. My 18th birthday, you’ll be back in my arms, my prom, and I want to get pregnant and have a baby with you after January. I want to get pregnant so the baby is born after I graduate since it takes 9 months.”
In an interview, Rivera told us that Vanessa — whom he met when they were in elementary school at PS 158 on the Upper East Side — wrote to him almost every day during his stretch for assault, during which he joined the infamous Latin Kings gang.
Her notes are littered with the code “831,”
meaning “I love you” (as in: eight letters, three words, one meaning) and always with the return address at her upscale Sutton Place address. She stuck with Rivera despite a privileged upbringing provided by her mother, Bonnie Haydon, the owner of a modeling agency, and her late stepfather Charles Haydon, a famed Manhattan attorney.
But Vanessa — who became a student at the $147,000-a-year Upper West Side prep school Dwight — also grew increasingly attracted to the gang lifestyle, according to Rivera. And in the letters she wrote to him while he was inside, she described her own flirtation with thuggish behavior.
“Lately people in my bitch ass school are acting like bitches, and today I flipped,” she wrote, “I went up to shorty, Jen, and confronted her about something.”
Vanessa describes how an argument between the two girls escalated into a fight, saying, “I pushed her and our hands were together pushing each other so I slammed her against the wall holding her against the wall, screaming at her.”
Even though she was never a gang member herself, Vanessa intimates she could have been developing a reputation because of her relationship with Rivera: “People honestly were scared for her, because . . . people have heard about me, and they didn’t want any s--t happening.”
But of Rivera’s gang activity, Vanessa — who sometimes addresses Rivera as “King” in the messages — warned him, “So if you are “L.K.” [Latin King] just remember please stay out of trouble and just chill and be good because no one loves you as much as I do.”
She also seems jealous of his brotherhood with other members of the gang, founded in Chicago in the 1940s and spread to New York prisons in the ’80s.
“When we get in conversations about the ‘Latin Kings’ I just want you to act the same for me,” she wrote, “and always be there for me because I obviously don’t want to lose you, I just want you to do the best you can and stay out of trouble because I can’t go through you getting locked up [again].”
But her letters are also often heated, offer- ing a glimpse at the young couple’s difficult circumstances. In one message approximately six months into his term at an upstate prison, seemingly in a moment of frustration and despair, Vanessa even tried — unconvincingly — to break up with him.
“I know it’s tough for you up there and I don’t do anything to help the situation. And I love you and I want you more than just a phone call,” she wrote, “I want to be able to hold you and make love to you, but that can’t happen. So my decision is for the best and only the best, but whenever you need someone to talk to or if you need clothes or anything, I’m here, just call.”
After several more stints in prison, Rivera left the gang for good. He ended his relationship with Vanessa when she was around 20 and a model — and after he discovered she had been unfaithful to him with actor Leonardo DiCaprio.
Vanessa went on to meet Donald Trump Jr. in 2003 and married him in 2005 at his father’s Mar-a-Lago estate in Palm Beach, Fla. After having five children with Donald Jr., she filed for divorce in March of this year.
Rivera has turned his back on his gangland past and now has a steady job and a family. But even though he has moved on with his life, he says he has never been able to part with his love letters from Vanessa.
“Vanessa was my first love,” he explained. “She even gave me a photo album full of pictures of her, and us together, with a note saying, ‘This is so you can remember me when I become famous.’ ”
“You know, she was right, she did become famous — but the Vanessa people see with Trump isn’t the Vanessa I knew.
“She always wanted to become a mother, but she was also a much stronger, independent and fiery woman. She had big dreams. She’s a fighter.
“I hope she finds happiness in the next chapter of her life.”
A spokeswoman for Vanessa Trump said, “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.”