Vanessa Trump has quite the wild dating history.
The ex-wife of Donald Trump Jr. has been in the headlines a lot lately after Tiger Woods took to social media over the weekend to confirm rumors that the two are dating:
“Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”
Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts. pic.twitter.com/ETONf1pUmI
— Tiger Woods (@TigerWoods) March 23, 2025
Kind of a wild move for one of the biggest athletes in the world to ask for privacy while announcing your relationship with a member of the most famous family on the planet. Not sure that’s how this works, Tiger.
Vanessa Trump is the 47-year-old ex-wife of Donald Trump Jr. who were married for 13 years before getting divorced back in 2018. The two have five children together, including 17-year old Kai Trump, who like her grandfather is an avid golfer herself and has become a popular social media personality over the past year or so.
But believe it or not, Donald Trump Jr. and Tiger Woods isn’t even the wildest thing about Vanessa Trump’s romantic history.
The New York City native grew up attending an exclusive private school in Manhattan. But according to an interview with People in 2018, her high school boyfriend was a violent street gangster named Valentin Rivera, a member of the Latin Kings, who has spent time in prison for things like assault and negligent homicide.
Vanessa would drive Rivera to his gang meetings (I didn’t realize street gangs had meetings) and drug deals, but eventually the two split in 1998 after Rivera discovered that Vanessa was cheating on him – with Leonardo DiCaprio.
Yes, that Leonardo DiCaprio, who at the time was one of the biggest actors in the world following the success of Titanic the year before.
But the relationship between the two didn’t last long, because Vanessa soon moved on to her next relationship, Saudi prince Khalid bin Bandar bin Sultan Al Saud.
The relationship between the two was apparently pretty serious, with the two even planning on getting married. But then, something happened that would force them to go their separate ways: The September 11th terrorist attacks.
Khalid bin Bandar’s father, Bandar bin Sultan Al Saud, served as the Saudi ambassador to the United States from 1983 to 2005. But in 2001, phone numbers that were indirectly linked to Bandar were found in the phone book of Al Qaeda recruiter and Saudi national Abu Zubaydah, a senior lieutenant to Osama Bin Laden who was closely involved in the planning of the 9/11 attacks.
This led to suspicions that Bandar was somehow involved in the attacks, allegations which he fiercely denied, insisting that Saudi Arabia had nothing to do with the attacks and calling it “the worst thing to happen to us.”
Khalid bin Bandar left the United States and ended his relationship with Vanessa Trump due to his father’s suspected ties to the hijackers.
Ultimately though, a CIA report determined that “no evidence that either the Saudi government or a member of the Saudi royal family knowingly provided support” for the terrorist attacks, and Bandar continued to serve as ambassador to the United States until 2005.
Vanessa would then move on to Donald Trump Jr., her longest relationship to date, before the couple split a few years ago. But it seems like she’s got a thing for the bad boys: Tiger has obviously had his own troubles in the past, but those don’t really compare to a gang member and a Saudi prince with suspected ties to the 9/11 hijackers.
Quite the relationship history she’s building here.
Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts. pic.twitter.com/ETONf1pUmI
— Tiger Woods (@TigerWoods) March 23, 2025
