Photos of Vanessa Trump in Her Modeling Days and Her Mysterious Relationship With Leonardo DiCaprio

It seems the Trump family is always making headlines these days, especially now that Donald Trump Jr. and Vanessa Trump have announced their plans to divorce. While the news came as a shock to many, it seems the former couple is trying to keep things amicable, especially because they have five children together.

And while we know an awful lot about Donald Trump Jr. (too much at times, in fact), Vanessa Trump has stayed more out of the spotlight. But she actually has a pretty fascinating past, including a modeling career and a relationship with none other than Leonardo DiCaprio.

Vanessa’s modeling days

Vanessa Trump on a modeling runway.

Vanessa was an experienced model when she started dating Donald Trump Jr. | William West/Getty Images

Vanessa has been modeling since she was a child — her mother, Bonnie Haydon, ran the agency Kay Models. She was a natural, though. In fact, she was modeling when she met Donald Trump Jr.

Next: Vanessa was a bit of a wild child in her younger days.

An ‘ill  thug’?

Vanessa Trump modeling for Tommy Jeans.

Vanessa seems posh to the rest of us, but her high school classmates thought differently. | Donald Trump Jr. via Instagram

Despite her prestigious New York City upbringing, Vanessa was a little different than you might expect in high school. One former classmate referred to her as a “total gangster bitch,” while another said, “She was an ill thug. She went out with this Latin King for like three years.”

Next: Wait until you hear what her classmates nominated her for.

Most likely to what?

Donald Trump Jr and Vanessa Trump posing for a photo together.

She appeared to have loved drama. | Bryan Bedder/Getty Images For IMG

According to the same former classmates, Vanessa was voted “Most Likely to Wind Up on Ricki Lake” by her high school friends for the yearbook. She didn’t ever go on Ricki Lake, but her marriage to Donald Trump Jr. definitely put her name on gossip sites, such as Page Six.

Next: It seems Vanessa got two yearbook nominations.

This one came true

Donald Trump Jr. sits with Vanessa Trump.

Her high school friends jokingly predicted her divorce. | Jeff Swensen/Getty Images

Apparently, Vanessa was also voted “Most Likely to Get a Divorce” by her high school classmates. Apparently they were only half wrong in their predictions.

Next: Did she date DiCaprio?

Vanessa and Leo?

Leonardo DiCaprio and Vanessa Trump collage.

Left: In 1998, Leonardo DiCaprio was quite the bachelor. | Brenda Chase/Getty Images, Right: Did Vanessa Trump really date the star when she was a young model? | William West/Getty Images

Vanessa was only 20 years old when she allegedly briefly dated Leonardo DiCaprio. The two were spotted nuzzling at NYC’s Moomba restaurant in 1998 during the Two Girls and a Guy premiere party, and they were also seen together a couple of other times.

Next: Some say the Leo rumor is fake news.

Did Vanessa fake her relationship with Leo?

Vanessa Trump posing with a designer at a fashion show.

The model’s relationship with the Leonardo DiCaprio didn’t go very far. | William West/Getty Images

Some say Leo and Vanessa never actually dated, and it was Vanessa herself who spread the rumor. Sources claim she bragged about being the woman who made Leo want to be monogamous when he’d been known for dating numerous models at once. But she was really just using his name to make herself famous. Of course, it’s impossible to know for sure.

Next: What’s next for Vanessa?

Will she come out of retirement as a single woman?

Vanessa Trump poses at the Imperia Vodka booth during Mercedes-Benz Fashion Week Fall 2008.

She might consider returning to modeling. | Getty Images/Getty Images for Imperia Vodka

Vanessa Trump is now 40, and while some might say she’s past her modeling prime, there’s no doubt she could find work with her impressive resume. She’ll be very busy taking care of her five children, but she’ll still have plenty of options for professional pursuits. And because her soon-to-be-ex-husband is reportedly very stingy, she might need them.

Next: Surprising photos of Don Jr. that show a different side of him

He plays in the snow with his daughter, Kai

Donald Trump Jr. and his daughter Kai playing in the snow.

He doesn’t mind getting rough in the snow. | Donald Trump Jr. via Instagram

Don Jr. and Vanessa Trump have five children together, which certainly makes their life hectic. And one source told Page Six in the past that Don Jr.’s constant traveling put a major strain on his marriage and home life. The source says it was tough for the couple to resolve their issues since he was never around.

Nevertheless, Don Jr. proves he still has enough time to play one-on-one with his kids. Here, his daughter Kai and him look like they’re having fun in the snow.

Next: Don Jr. seeks comfort from his kids during his difficult divorce. 

He cuddles with daughter Chloe after the divorce news hit the media

Donald Trump Jr. and his daughter Chloe.

He’s putting his children first. | Donald Trump Jr. via Instagram

Divorce is difficult on anyone, and we can’t imagine the added stress of being under the political spotlight. Either way, Don Jr. hasn’t made any comments about his divorce on social media just yet — but he did post this adorable photo of him and his daughter Chloe.

The comment alludes to tough times for him, as it read, “No matter what is going on bedtime cuddling with the smurf puts a Yuge smile on my face.” He also may be poking fun at his dad with the usage of “Yuge” here — so perhaps he has more of a sense of humor than we thought.

Next: These photos are sweet, but they point to a troubled history for Don Jr. 

Don Jr. fishes with his son, Donnie

Donald Trump Jr.'s collage of him fishing with his children.

He spends time fishing with his son. | Donald Trump Jr. via Instagram

We know by now that Don Jr. loves the great outdoors. And here, he’s fishing to celebrate his son’s 9th birthday. The photo shows a compilation of Don Jr. and young Donnie on their many fishing adventures, and the two look like they’re having a blast.

These photos remind us of the scandalous hunting pictures of Don Jr. and Eric Trump that shocked the public, however. In the photos, the two were holding up dead big-game carcasses — and Don Jr. even help up an elephant’s tail detached from its body. The whole thing seemed in poor taste.

Next: He even brought his five kids to this monumental event. 

He involves his kids in the political action

Donald Trump Jr.'s instagram photo.

He recently shared this memory. | Donald Trump Jr. via Instagram

When Don Jr. isn’t taking care of his family or traversing the globe for fun, he’s giving his dad a hand in politics. And here, he posts a throwback photo of his whole family while his father was sworn as the 45th president.

Does Don Jr. expect his own kids to get into the political action as they age? We can’t say for sure, but he did share a photo of his daughter, Kai, at Donald Trump’s desk. Us Weekly reports he captioned the photo, “Kai Trump 2060??” Perhaps a few of his kids have already taken an interest.

Next: He’s also introducing his kids to the Trump family’s favorite sport. 

He posted this photo of his kids playing golf for his birthday

Donald Trump Jr.'s children playing golf.

He keeps his children active. | Donald Trump Jr. via Instagram

He’s not just exposing his kids to politics young — he’s also getting them involved in the family’s treasured sport of golf. Here, he shows a side-by-side image of young Spencer and Chloe on the golf course holding their gear. According to the caption, the family went golfing for Don Jr.’s 40th birthday.

In case you didn’t know, Eric and Don Jr. also opened up a Trump International Golf Course in Dubai. Perhaps this is one of the reasons he’s traveling abroad all the time in addition to hunting big game.

Next: A rare photo of the whole family, his wife included 

The whole family gets together for the holidays

Donald Trump Jr's holiday family photo.

Family events are important to him. | Donald Trump Jr. via Instagram

Here, Don Jr. and his whole family are celebrating the holidays together — and he even adds a heartfelt message to his Instagram post. It reads, “Merry Christmas,” as well as, “May your day be as joyous as anyone could possibly hope for.”

The sentiment and photo are nice — but something does seem a little off. Don Jr. and his wife are incredibly far away from each other here. And in general, Don Jr. never seemed to post too many photos of him and Vanessa. Perhaps we should have seen this divorce coming a long time ago.

Next: He has more of a sense of humor than we thought.

Don Jr. pokes fun at his dad more often than we expected

Donald Trump Jr. and his two children.

He doesn’t take himself too seriously. | Donald Trump Jr. via Instagram

When he’s not stirring up controversy on social media, he’s busily making lighthearted punches at his presidential father. Here, we see Chloe and Spencer coiffing Don Jr.’s hair in a classic Trump style while they’re holding hairbrushes. Don Jr. writes, “I’m not sure about this look but given the whole Trump hair thing who am into judge???”

Whether you’re a Trump fan or not, there’s no denying Don Jr. seems like a very involved father. And there’s enough evidence on Instagram to suggest he’s a fun-loving dad.

Additional reporting by Lauren Weiler.

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