From her privileged upbringing and modeling career to her high-profile divorce and rumored new romance, here’s a closer look at the woman who was once part of the Trump inner circle.
Born into wealth and raised in New York’s elite social circles, Vanessa Trump’s life always seemed destined for the spotlight. She pursued modeling and eventually married into one of the most talked-about families in the country.
But after twelve years and five children, her marriage to Donald Trump Jr. came to an end. While the world watched their split unfold, Vanessa remained private — until new reports surfaced suggesting she may have moved on with another household name. Read on to learn more about the brunette beauty.
Vanessa’s Early Life and First Meeting with Donald Jr.
Vanessa was no stranger to the spotlight long before she became a member of one of America’s most famous families. Raised in a townhouse on the Upper East Side, she grew up in a world of privilege.
Despite her deep roots in New York society, Vanessa’s romantic connections spanned diverse backgrounds. In 2018, reports surfaced that before meeting Donald Jr., she had been involved with Prince Khalid bin Bandar bin Sultan Al Saud.
Her mother, Bonnie Haydon, ran the Kay Models agency, setting her daughter on a path in the fashion industry from an early age. Signed to Wilhelmina, Vanessa spent years modeling while also excelling as a student and athlete at the Dwight School on the Upper West Side.
With her athletic build, golden tan, and bright smile, she was known for her easygoing nature and preference for casual fashion — often choosing jeans over high-end designer outfits. Her friend Shawn Modell recalled that Vanessa prioritized close-knit friendships over social climbing.
Despite her deep roots in New York society, Vanessa’s romantic connections spanned diverse backgrounds. In 2018, reports surfaced that before meeting Donald Jr., she had been involved with Prince Khalid bin Bandar bin Sultan Al Saud.
Sources claimed that the two dated from 1998 to 2001 and even lived together, planning to marry. However, after the attacks on September 11, 2001, Khalid abruptly left for Saudi Arabia.
A second insider reported that the Saudi prince treated Vanessa “as if she was his queen. It was the complete opposite from Don Jr. They were together 24/7. They were a real couple.”
However, another source disputed the seriousness of their relationship, stating that while they dated in her early 20s, they had never lived together nor intended to wed.
Regardless of the differing accounts, Vanessa’s life took a very different turn when she crossed paths with Donald Jr.
Their first meeting in 2003 was anything but a grand romantic gesture. Vanessa recalled the introduction, saying:
“I’m at this fashion show. Donald Trump comes up to me with his son. ‘Hi, I’m Donald Trump. I wanted to introduce you to my son Donald Trump Jr.'”
The conversation that followed was brief and awkward. Later that evening, Donald Sr. spotted Vanessa again and reintroduced her to his son, apparently forgetting they had already met. She humorously responded, “Yeah, we just met, five minutes ago.”
Six weeks later, fate intervened again. At a birthday party in New York, a mutual friend introduced them for a third time. Neither initially remembered their previous encounters, but as they spoke for an hour, something clicked. This time, they made a lasting
An engagement soon followed. However, it was not without controversy. Donald Sr. had publicly reprimanded his son on “Larry King Live” for accepting a free engagement ring from a New Jersey jeweler in exchange for a public announcement of the proposal.
“You have a name that is hot as a pistol, you have to be very careful with things like this,” the elder Trump warned. Nonetheless, on November 12, 2005, they married at Mar-a-Lago, the Trump family’s club in Florida, marking the beginning of Vanessa and Donald Jr.’s journey together.
After saying “I do,” Vanessa and Donald Jr. wasted no time in starting a family. In 2007, they welcomed their first child, daughter Kai Madison. Arriving almost three weeks early, she weighed six pounds and 14 ounces.
Donald Jr. shared his excitement, saying, “Everyone’s great. Baby’s great, Vanessa’s great — and I’m getting used to the idea [of being a father].”
“[Yesterday was] a hectic day [due to the early birth, but] it’s definitely a changing experience. It’s very cool. [Kai is named after her maternal] grandfather. It’s Danish. He’s a Danish musician, and we wanted to keep it as a family name,” he added.
Their family continued to grow with the birth of their son, Donald John III, on February 18, 2009, in New York. He weighed eight pounds, 11 ounces, and measured 21 ½ inches long.
Two years later, in October 2011, they welcomed their third child, Tristan Milos Trump. “Tristan Milos Trump was born at 2:59 a.m. on Sunday, October 2,” the couple announced.
“He weighed eight pounds, four ounces, and came a week early. Mom and baby are doing great. He looks forward to meeting you all!” they continued. The bundle of joy’s middle name, Milos, honored his paternal great-grandfather, Ivana Trump’s father.
In March 2018, Vanessa and Donald Jr. decided to end their marriage after 12 years and five children together. The couple released a joint statement confirming their split.
In 2014, their family expanded again with the birth of their fourth child, a daughter. Donald Jr. shared the news on social media, writing, “It’s a girl!!!! @MrsVanessaTrump and I are very excited to be bringing home our little bundle of joy today. #FullHouse.”
Their fifth and final child, daughter Chloe Sophia, arrived in June 2020. Born at 11:56 p.m., she weighed in at eight pounds and six ounces. With their growing brood, Vanessa and Donald Jr. built a large and lively household, embracing parenthood amid their high-profile lives.
Filing for Divorce and Moving On with Someone New
In March 2018, Vanessa and Donald Jr. decided to end their marriage after 12 years and five children together. The couple released a joint statement confirming their split.
“After 12 years of marriage, we have decided to go our separate ways. We will always have tremendous respect for each other and our families,” they shared. “We have five beautiful children together and they remain our top priority. We ask for your privacy during this time.”
According to court records, Vanessa filed the divorce papers in the Manhattan Supreme Court. Page Six, which first broke the news, reported that she filed for an uncontested proceeding.
Before filing for divorce, Vanessa was praised for how she managed life as a mother of five.
This came on the heels of growing speculation that the pair’s marriage was on shaky ground. A source who socialized with the couple revealed:
“I heard for a while they have been living separate lives… Even before all this Trump presidency stuff started they weren’t good and their marriage was strained.”
Yet another source close to the Trump family described the news as “surprising,” saying, “They always seemed very cute together, and were a really fun couple.” Legal experts weighed in on the split, speculating that a prenuptial agreement was likely in place.
“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,” said divorce attorney Michael Stutman of Stutman Stutman & Lichtenstein LLP. He was not involved in the case.
Before filing for divorce, Vanessa was praised for how she managed life as a mother of five. Her estranged husband’s sister, Ivanka Trump, spoke to PEOPLE in July 2016, saying, “My sister-in-law Vanessa is a machine. She can take all of [my children] and not even notice. She has five children, and she’s Wonder Woman to me.”
Despite their differences, Vanessa and Donald Jr. committed to co-parenting their children. “Donald Jr. and Vanessa are not fond of each other, but will do what is necessary to protect the kids from any issues,” a social source close to the Trumps revealed.
“They are co-parenting, and while Vanessa is a hands-on mother and always there, Donald is also a good father. He is around for his kids. But he has his own place in [upstate] New York,” the source added, referring to Donald Jr.’s cabin in the Catskills, where he often spent weekends hunting and fishing.
“He has many hobbies and interests, and is sort of a loner so he will be fine whether or not he finds someone else right away or not,” they explained.
A political source close to the family also said the former couple would continue to co-parent and interact during family events but noted that the former couple “aren’t friends.” They added:
“They may intersect a day or two on vacations, but I don’t think they will be vacationing together unless there are separate accommodations in a large place for each and they divide the kids between them.”
According to insiders, Donald Jr. is “cool” with his ex-wife and her new relationship.
It’s been seven years since Vanessa filed for divorce, and according to reports, she has found love again — this time with golf legend Tiger Woods.
Four sources confirmed to DailyMail.com that Vanessa and Tiger began seeing each other shortly before Thanksgiving. Both live just 20 minutes apart in Palm Beach, Florida, and were spotted together at a golf tournament the month prior.
Vanessa’s eldest daughter and Tiger’s’ children, Charlie and Sam, all attended The Benjamin School, which costs $38,595 a year. Beyond geography, Vanessa and Tiger’s families have shared common interests as well, as Kai is reportedly a top golfer herself.
“They just love hanging out, having dinner, and schmoozing together. They’re sticking close to home, have decided not to make it a thing and go out in public. Not just yet anyway,” a source revealed.
Another added, “She comes to his place on Jupiter Island. They’re not living together. She comes over maybe a few nights a week.” According to insiders, Donald Jr. is “cool” with his ex-wife and her new relationship.
Since the official split from Donald Trump Jr., Vanessa had not been publicly linked to anyone else before Tiger. Their pairing could mark what some described as golf’s new power couple.
In addition to her budding romance, Vanessa has also garnered attention for her stunning appearance over the years.
“What shape you stay in after 5 kids wow,” one netizen commented on a post the blonde shared of herself doing archery practice in 2016. “Wow! She is great!” someone else wrote while a third person added, “Nice.”
A little archery practice in my backyard pic.twitter.com/R5og8xmt47
— Ms Vanessa Trump (@MrsVanessaTrump) September 2, 2016
After twelve years of marriage and five children with Donald Trump Jr., Vanessa stepped away from the political spotlight and focused on raising their family. While their divorce marked the end of one chapter, reports suggest she may have found a new beginning with another well-known figure.
