Yesterday, the Daily Mail published a story that claimed, based on several inside sources, that Vanessa Trump and Tiger Woods are dating. They have apparently been dating since Thanksgiving.
Now, if you’re not aware, Vanessa is Donald Trump Jr.’s ex-wife. They were married from 2005 to 2018 and have five children together, including Kai Trump who has become quite famous in the last year.
Vanessa had an interesting dating history before Don Jr. In 1998, she briefly dated Leonardo DiCaprio. From 1998 to 2001, she dated a Saudi prince named Khalid bin Sultan Al Saud. Khalid’s mother’s father was King Faisal bin Abdulaziz, who was King of Saudi Arabia from 1964 until his assassination in 1975. Vanessa and Khalid intended to marry, but unfortunately, fate stepped in on 9/11/2001. Immediately after the attacks, Khalid was called back to Saudi Arabia because his father was suspected of having connections to the 9/11 hijackers. Today, Khalid is Saudi Arabia’s ambassador to the United Kingdom.
One night in 2003, Donald Trump and Don Jr. were attending a fashion event when the father spotted Vanessa. As Donald Sr. later recollected on an episode of “The Oprah Winfrey Show” in 2011:
“She looked so beautiful. I said, ‘Don, that’s the person you should marry.'”
As Vanessa later recounted in an interview, at that fashion event, Don Sr. embarrassingly kept introducing her to his son, forgetting that he had already made the introduction.
In November 2004, Don Jr. proposed to Vanessa with a $100,000 diamond ring that he received for free from a jeweler in exchange for proposing in front of the store at the Short Hills Mall in New Jersey while paparazzi snapped photos.
Look. Am I going to sit here and claim that I would not have accepted a free $100,000 ring in exchange for a cheesy photo-op setup? No. But I’m also not the son of a billionaire, and I think that’s what makes this move pretty lame.
I just checked, and sure enough, one of the photos from that day is available for me to license from Getty. So I just spent the money for you to enjoy in all its glory:
(Photo by Mychal Watts/WireImage)
Here is the description that goes along with the photo:
“November 11, 2004: Vanessa Haydon, fiance and Donald Trump Jr. during Bailey Banks and Biddle Fine Jewelers Provides Diamond Engagement Ring for Donald Trump Jr.’s Fiancee Vanessa Haydon at Short Hills Mall in Short Hills, New Jersey, United States.”
Anyhoo.
Vannessa’s dating history is actually not my favorite story about her.
A Saucy Investment
Vanessa Haydon grew up on the Upper East Side of Manhattan. Her mother ran the Kay Models agency, which probably helped when teenage Vanessa decided to pursue a modeling career. Her mother’s second husband, Charles Haydon, was actually her stepfather. He’s frequently referred to as her father, but he is actually her stepfather. I couldn’t find any information about her birthfather, but Vanessa’s legal birth name is Vanessa Kay Pergolizzi, so I’m guessing it’s a guy whose last name is Pergolizzi.
There’s a restaurant in New York called Rao’s that has been around since 1896.
A century later, in 1992, the restaurant wanted to expand into selling pasta sauce commercially. Needing some capital to launch this new side business, Rao’s took on a $1 million investment from… Charles Haydon. In exchange, Charles received a 30% stake in the commercial business, not the restaurant.
(CelebrityNetWorth Original Image)
Marinara Millionara
Unfortunately, Charles died in 1995. He left his 30% stake in equal parts to Vanessa and her mother (15% each).
In 2017, Rao’s was acquired by a competing consumer brand conglomerate for $415 million. With the acquisition, Vanessa and her mother split a $125 million windfall, $62 million a piece, pre-tax. They both became overnight marinara millionaras.
When her mother dies, Vanessa will be the sole heir to the Rao’s windfall. Her full inheritance will easily be north of $100 million, all in with real estate and other sources of family wealth that were created outside of marinara.
(Photo by Chip Somodevilla/Getty Images)
Love on the Links? Vanessa and Tiger Woods
Vanessa’s love life continues to be anything but boring.
If she is indeed dating Tiger Woods it would make a lot of sense. They both live in Palm Beach and have kids at the same elite school, The Benjamin School, where tuition costs $38,000 per year. They have been spotted together, including at a PGA Tour event where Vanessa’s daughter Kai wore Tiger’s golf merch. While neither has confirmed the relationship, the speculation is in full swing. Whether this is just a friendly pairing or something more, one thing’s for sure—Tiger knows a thing or two about driving, and Vanessa’s got the sauce to keep things interesting.
