Vanessa Trump, born Vanessa Kay Pergolizzi on December 18, 1977, has led a life filled with privilege, fame, and family. She grew up on Manhattan’s Upper East Side, attending The Dwight School, and later Marymount Manhattan College. Her mother, Bonnie Haydon, ran the Kay Models agency, which paved the way for Vanessa’s own career in modeling. She was signed with Wilhelmina Models in the 1990s and even had a brief acting stint, including an appearance in the 2003 film Something’s Gotta Give.
In 2005, her life took a major turn when she married Donald Trump Jr., the eldest son of U.S. President Donald Trump. Over the next thirteen years, they had five children together: Kai, Donald John III, Tristan, Spencer, and Chloe.
Who Are Vanessa Trump’s Kids?
Kai Madison Trump, the eldest, was born on May 12, 2007. As the first grandchild of Donald Trump, she quickly found herself in the public eye. She inherited her family’s competitive streak and pursued a career in golf, gaining attention for her skills on the course. In 2024, she made headlines by committing to the University of Miami’s golf team, securing a future in the sport before even finishing high school.
But Kai isn’t just about golf. She also stepped into the political arena in July 2024 when she spoke at the Republican National Convention, making her the first of Donald Trump’s grandchildren to address such a major political event. In her speech, she gave a rare glimpse into her grandfather’s personal side, calling him a “normal grandpa” and sharing anecdotes about his encouragement and support. Her massive Instagram following—1.6 million as of early 2025—proves that she’s not just riding on her family name but building a personal brand of her own.
Kai Madison Speech at the RNC stage. Your thoughts? be nice! 🤠 pic.twitter.com/RRYJR1YicC
— KAI TRUMP OFFICIAL 🇺🇸 COMMENTARY (@KaiTrumpJr) January 5, 2025
Donald John Trump III, often called Donny, followed on February 18, 2009. While he tends to keep a lower profile compared to his sister, he is an active participant in family traditions, including hunting trips with his father. He, along with his younger brothers, joins Donald Trump Jr. on their annual North Carolina hunting expedition, a tradition that’s been going strong for over eight years. Donny also shares a close bond with his siblings and is known for his outdoorsy interests, much like his father.
Tristan Milos Trump, born on October 2, 2011, has already had a few notable moments in the spotlight. At just five years old, he suffered a broken leg while skiing in Aspen, Colorado, requiring a hospital visit with Secret Service agents accompanying him. He is also an avid football fan, celebrating his 12th birthday in October 2023 with a Buccaneers-themed cake. His father, Donald Jr., posted a heartfelt message calling him “T-man” and expressing pride in the young man he’s becoming.
Spencer Frederick Trump came into the world on October 21, 2012, just a year after Tristan. Like his older siblings, Spencer enjoys outdoor activities and has developed a close bond with his father. In November 2023, he accompanied Donald Jr. on a boys’ trip to South Dakota, where they participated in a hunting expedition. Despite the trip’s wholesome father-son bonding, Spencer couldn’t resist some playful mischief—his dad later shared that the young boy “ball punched” him just moments before they posed for a photo.
Chloe Sophia Trump, the youngest, was born on June 16, 2014. Despite her young age, she’s already showing an interest in golf, following in the footsteps of her older sister Kai. In 2024, Vanessa shared a video of Chloe and Kai practicing their swings on the golf course, referring to them as her “two golf superstars.” But Chloe’s talents don’t stop there. She also captained the family’s boat in the summer of 2024, confidently steering while her father documented the moment. While she may be the youngest, she certainly isn’t one to be left behind.
Vanessa Trump Is Dating Tiger Woods Following Her Divorce From Donald Trump Jr.
Vanessa and Donald Jr.’s marriage, though long-lasting, eventually came to an end. On March 15, 2018, Vanessa filed for an uncontested divorce in New York. By the end of the year, the split was finalized, with both parents maintaining a commitment to co-parenting their five children. The divorce was initially described as amicable, though later reports hinted at financial strains and disagreements over Trump Jr.’s increasing involvement in politics.
Despite their separation, Vanessa has remained largely out of the political spotlight, focusing on raising her children in Palm Beach, Florida. However, recent reports suggest she has reentered the public eye due to a rumored relationship with golf legend Tiger Woods. The two reportedly began dating around Thanksgiving 2024, with sources claiming that Vanessa frequently visits Woods’ home in Jupiter Island but does not live there. Interestingly, their connection seems to stem from their shared love of golf—Vanessa’s daughter Kai and Woods’ kids, Sam and Charlie, all attend the prestigious Benjamin School in Palm Beach and share a passion for the sport.
Tiger Woods, who has not been married since his 2010 divorce from Elin Nordegren, has been linked to several high-profile women over the years, including Olympic skier Lindsey Vonn and nightclub manager Erica Herman. However, sources suggest that his relationship with Vanessa Trump is different, with one insider stating, “They share a lot of the same values and like to avoid drama.” Their relationship has yet to be publicly confirmed, but the couple has been spotted together at multiple golf tournaments, including the Genesis Invitational in February 2025.
