Vanessa Trump Might Have Never Divorced Don Jr. If It Weren't For This One Thing
Maybe it's something about the name, but Donald Trump Sr. and his oldest son Donald Jr. haven't had the best track record when it comes to romance. Both the former president and former first son have been through unpleasant divorces before finding their current loves. Donald Sr. has been wed since 2005 to Melania Trump, with whom he may have a somewhat unconventional marriage. Coincidentally, Don Jr. also married that same year, to former model Vanessa Haydon. That union lasted until 2018 when Vanessa filed for divorce and custody of their five children. But if not for a stroke of financial luck, Vanessa might still be part of the presidential family.
According to an exclusive report from Page Six, Vanessa's stepfather, Charles Haydon, happened to be good friends with Frank Pellegrino Sr. and Ron Straci, owners of the century-old Rao's Italian restaurant in upper Manhattan. In 1992, the restaurateurs branched out into merchandising, launching a specialty food business that sells the restaurant's famous pasta sauce and other delicacies. Haydon invested six figures into Rao's in exchange for 30 percent ownership. Then in 2017, the company was sold to a larger firm for an estimated $415 million, making a very tidy profit for Haydon and his heirs. The outlet speculates this was the motivation for Vanessa to leave her marriage: She and her children could now live in luxury without having to depend on the Trump fortune.
Vanessa Trump's financial status may have prompted the divorce
While Donald Trump Jr. and the former Vanessa Haydon have never disclosed the reasons behind their divorce, there are plenty of possibilities from which to choose. An insider has told Page Six the union was troubled from the start, and Don Jr.'s behavior as a husband and dad didn't help matters. "She hates that he posts stuff online, pictures of their kids and how he paints the picture of him as a perfect father like he's Mr. Dad," dished the source. "It's not the truth. And when he's not away on business trips, he's hunting and fishing."
Then there was the alleged affair between the junior Trump and singer Aubrey O'Day of Danity Kane, whom he'd met on "The Celebrity Apprentice." According to Us Weekly, Vanessa discovered texts between the two that revealed the infidelity. Reportedly, a furious Vanessa called O'Day while her children were in the room in an effort to embarrass the singer. O'Day would later confirm the relationship to Page Six, calling Don Jr. her "soulmate" and adding "I'll always have love for him."
The Trumps tried to move on, but tensions continued to grow, and having Don Jr.'s father in the White House only intensified the trouble. Yet another Page Six report claims Don Jr. "[kept] her on a tight budget. ... He treats her like a second-class citizen." That being the case, the sudden change in Vanessa's financial situation may have provided just the out she needed.
There's a new Mrs. Trump in the future
The former Mr. and Mrs. Donald and Vanessa Trump Jr. have since moved on from their ill-fated marriage. On New Year's Eve 2022, the former first son announced his engagement to Kimberly Guilfoyle, a former model who transformed herself into a Fox News host. Guilfoyle now hosts a podcast in addition to charity ventures and appearances at Republican events. As of this writing, no wedding date has been announced.
Guilfoyle doesn't seem to be in a hurry, however; on Valentine's Day 2024, she posted a gallery of happy couple pics and an effusive message: "Being with you fills my heart with joy and love every single day. Thank you for being my rock, my partner, and my best friend. Here's to many more adventures and endless love together. I love you more than words can express!" (Don Jr.'s sentiment was short and to the point: "Happy Valentine's Day, @kimberlyguilfoyle. I love you.")
Meanwhile, on February 24, the Daily Mail spotted Vanessa Trump driving away from the Trump International Golf Club, along with her son Tristan and a man believed to be a former member of the Secret Service detail assigned to then-president Donald Trump. While it's possible Vanessa still employs the guard as personal protection, the outlet teased the possibility of a budding romance. If so, it wouldn't be the first White House meet-cute; back in 1979, first daughter Susan Ford married Secret Service agent Chuck Vance.