Trump Family Exes Who Have Had A Major Transformation

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From red flags in Donald and Melania Trump's marriage to worries about Ivanka Trump and Jared Kushner's relationship, the Trump family's love lives can't seem to stay out of the headlines. The family's patriarch, Donald, by no means helps himself, though. For example, in 2017, France's former First Lady, Carla Bruni, had to publicly deny she had an affair with Donald after he claimed, in a Netflix documentary of all places, they'd had romantic rendezvous. Yeesh. It's fair to say many of the Trump family relationships have red flags we can't ignore.

Although the Trumps understandably take all the attention because, at the end of the day, they're one of America's few first families. It's important not to forget the exes themselves, many of whom have undergone major transformations since leaving the Mar-a-Lago-based family. So let's take a look at what happened to those who have left the Trumps via divorce or a break-up and, more importantly, how they've changed.

Ivana and Donald Trump had an infamously unamicable (and costly) split in the early 1990s after tying the knot in 1977. So, how much money was Ivana given after her divorce from Donald? Well, a cool $14 million, a 45-room Connecticut mansion, and an apartment in the Trump Plaza, as per the New York Times. That begs the question: What did she do with her settlement?

Ivana, perhaps taking lessons from her chameleonic ex-husband, became a Jack (or is it Jill?) of all trades. Like a proto-Kylie Jenner, she founded an eponymous fashion line and cosmetics brand called Ivana Haute Couture. "Ladies, you have to be strong and independent," she advised during her "The First Wives Club" cameo in 1996 (via the New York Post). "And remember, don't get mad – get everything!" Ivana practiced what she preached, that's for sure...

She even took her influence across the Atlantic, with the British sitcom "Absolutely Fabulous" using Ivana as an inspiration for one of their iconic characters. Ivana had transformed into a star of the silver screen, an influence on the small screen, and a disruptor in the fashion world. But she wasn't done there; she also became an author. Notably, her book, "Best is Yet to Come: Coping with Divorce and Enjoying Life Again," does exactly what it says on the tin in terms of showing how much she'd transformed. Despite publishing four books, perhaps the quote that best reflected her post-divorce metamorphosis came in a 1995 interview with the New York Times: "You don't have to put down the second name, Ivana is what the people call me."

When Marla Maples met Donald Trump, she was a beauty queen and had recently been crowned Miss Hawaiian Tropic. But after their divorce, she pivoted to become a very spiritual wellness guru. Perhaps taking up wellness is essential after living with Trump's diet of fast food, soda, and milkshakes. The first inclination of a sea change came in Maples' style transformation after her divorce from Trump. Her sartorial choices went from prim and proper while married to more flowy and spiritual post-divorce. A change that would also be mirrored in her business ventures...

After her divorce, she founded the Global Wellness Forum, which unites organizations to promote wellness, and became a Kabbalist (a believer in an obscure form of Jewish mysticism). As Marples' website puts it, she's "a passionate advocate for mental, spiritual, and physical wellness, offering inspiration and guidance to those seeking more joy, balance, and harmony in their lives. Whether it's through clean food choices or pausing to invoke a sacred connection." It's worth also noting that, in 2013, in quite a bizarre turn, Maples released an album that featured the Dalai Lama and Deepak Chopra. She'd come a long way from someone married to Trump, who has many outdated habits and is interested in unanimously unhealthy food choices.

After 13 years of marriage to Donald Trump Jr., Vanessa Trump opted for a quieter life following their divorce. It is probably welcome when you have the President of the United States discussing your divorce. "I happen to think the [Vanessa's relationship] with my son... was hurt very badly by the witch hunt that went on," said Trump, speaking from the Oval Office in 2025 (via The Independent). "[A]nd all the crap that they put Don through – who knew nothing about it." Not your average ex-father-in-law experience.

The former model was a red carpet fixture before and during her marriage, so her newfound low profile was a major change. Throughout her marriage to Donald Jr., Vanessa was involved in scandals that will always haunt her, from rumored romances to gang member exes, so it's understandable if she wanted a little more privacy than life as a Trump offered. The only exceptions that prove the rule are her appearances in family snaps on Donald Jr.'s Instagram and at major ex-in-law events. Thankfully, unlike other Trump family breakups, it all seemed pretty amicable. 

In 2025, Vanessa returned to the headlines when her new relationship with the lavish golfer Tiger Woods went Insta-official. "Love is in the air and life is better with you by my side," wrote Woods in a smitten Instagram post. "We look forward to our journey through life together." Despite the loved-up post, Woods and Vanessa's bank accounts reportedly prefer they skip the wedding bells. The pair did get Vennesa's ex-father-in-law's approval, though. All's well that ends well.

In the '80s, Blaine and Robert Trump ruled New York. But unlike Blaine's then-brother-in-law Donald Trump, she and Robert kept a relatively low profile as they made a major impact on the city. For example, in 1985, she began the God's Love We Deliver charity, which has delivered over 20 million meals to AIDs patients (as per Town and Country). Moreover, she began the charity at a time when many turned a blind eye to the disease. Props to Blaine.

Despite their keeping themselves to themselves, when the pair split in 2009, the divorce had all the signs of a tabloid hullabaloo. So, Blaine fled New York in favor of Miami. The truth about Robert Trump's ex-wife is that she moved back to Florida because it's where her family has roots, and so she could be closer to her beloved basketball team, the Miami Heat. "It was one of the darkest times in my life," Blaine told Park Magazine when speaking about her divorce and subsequent move cross-country. "And I feel lucky, and I feel grateful that I had the support of friends and family that got me through it." Although she stepped back from the spotlight, she still championed good causes and became a mental health advocate.

Although Blaine caused a stir with her Instagram post about Robert after his death in 2020, she has continued to shun the spotlight while dividing her time between Miami and New York. Her biggest post-divorce transformation was geographic.

Long before Ivanka Trump and Jared Kushner were brought together by a matchmaking friend, the former dated a few famous faces, and according to some sources, she even had a fling with Lance Armstrong in 2006. But, to use modern parlance, perhaps none of the Trump family exes on this list have had quite the fall off Armstrong had.

In 2012, the seven-peat Tour de France champion was hit with doping allegations that meant the cycle-champ had to hand back all his titles and Olympic medal. It's not a good look. Certainly not a good look for someone who prided themselves on athletic prowess and philanthropy. Armstrong denied the accusations for a while, which led people to ask if his ex-fiancée, Sheryl Crow, knew about Armstrong's scandal. However, in a 2013 interview with Oprah Winfrey, he came clean (if you pardon the pun). "This story was so perfect for so long. It's this myth, this perfect story, and it wasn't true," Armstrong admitted (via ESPN). "I viewed this situation as one big lie that I repeated a lot of times, and as you said, it wasn't as if I just said no and I moved off it."

Since then, Armstrong has certainly changed. "I would want to change the man that did those things, maybe not the decision, but the way he acted," he told the BBC in 2015. "The way he treated people, the way he couldn't stop fighting. It was unacceptable, inexcusable." Despite the controversy, it's an impressive and mature transformation.

Donald Trump's youngest daughter, Tiffany Trump, met Ross Mechanic at the University of Pennsylvania. The pair had a long-term romance at college, and they even held hands while they graduated together. Cute. However, things didn't get off to a good start for Tiffany and Mechanic after graduation when the former moved to Georgetown Law School to continue her education and became stressed. The stress equaled trouble in their relationship, and trouble equaled a break-up.

After the pair went their separate ways, Tiffany's ex clearly put his BSE in Computer Science to good use. After getting his start in tech, Mechanic became frustrated seeing big money being managed in Microsoft Excel. So, he founded and became the CEO of Maybern, an operating system for fund finance that automates complex calculations to improve their accuracy. In quite a Trumpian way, he saw a gap in the market and took it. To put a twist on a popular phrase: like your exes' father, like son. 

For a guy who used to post pictures on Instagram of himself drinking in the club, Mechanic raising $26 million in funding for his business, as per Forbes, shows how much he'd matured. From party boy to businessman, he has certainly graduated.

When Donald Trump, post-Ivana Trump break-up, met Rowanne Brewer Lane at a Mar-a-Lago pool party in 1990, she was a model and an extremely successful one at that. Before dating the future President, Brewer Lane was a contestant in the 1988 Miss USA competition and a winner (x3) on the TV talent show "Star Search." But their romance was short-lived. It ended when Brewer Lane upped sticks and moved to Los Angeles to follow the model-to-actress pipeline, à la Pamela Anderson or Emily Ratajkowski. But despite landing small roles, acting wasn't quite the same unmitigated success as her modeling career. Actually, she'd make her biggest transformation almost thirty years later, when she became a key figure in Trump's life once again. 

In the throes of the 2016 presidential campaign, The New York Times described Brewer Lane's aforementioned first encounter with Trump, then-Republican nominee, as anything but a meet-cute. Instead, they claimed, it pointed to a pattern of lechery from the potential president. Brewer Lane, however, saw it differently and claimed the paper misrepresented her version of events. "They spun it to where it appeared negative. I did not have a negative experience with Donald Trump," she told the Fox News show "Fox and Friends" (via Politico). "[A]nd I don't appreciate them making it look like that I was saying that it was a negative experience because it was not." It was a far cry from her appearances on TV as a variety show spokesmodel. Now, her words were pivotal to a presidential campaign.

James "Bingo" Gubelmann sounds like the name of a low-level mafia lackey in a Martin Scorsese film, so maybe his turn to crime was a case of nominative determinism? In 2016, almost ten years after dating the future Mrs. Kushner, Gubelmann was arrested in a cocaine bust alongside Maroon 5 guitarist Michael "Mickey" Madden in Manhattan's East Village. Ivanka Trump dated Gubelmann, a film producer by trade, for three and a half years before they split in 2005. In fact, she starred in one of his films, "Born Rich," which focused on rich heirs, and she gave the filmmakers a tour of her 68th-floor pad at Trump Tower. 

However, despite having a long list of films produced before and after his arrest, any cursory Google search of Gubelmann's name will show you headlines regarding his brush with the law alongside his movies. After his arrest, Gubelmann agreed to enter treatment so he could be released, alongside agreeing to a day of community service. It was quite a fall from grace, from a young up-and-coming filmmaker who dated a Trump to being cuffed (literally).

"We met each other like in a movie," said Jure Zorcic, a supposed pre-fame Melania Trump ex, spilling the tea to ABC News. "It was a hot summer day, in between wars in Slovenia [in 1991] ... I was on my motorbike, and she has been walking down a street. As I passed by her, I had a moment and thought, 'Wow, who is this girl? She is so beautiful, I must turn back and follow her.'" This supposed Slovenian love story blossomed from there, as the pair went for coffee and proceeded to date for several months. However, it transformed into a tragedy after their break-up.

As Zorcic tells it, Melania left Slovenia to begin a modelling career across Europe, which then took her to the States. The alleged exes later reconnected in the Big Apple, where Melania told him, notably in her second language of English, she'd never be coming back to her homeland (as per ABC News). Although it may seem like Melania was the one who'd undergone the most major transformation after their break-up, Zorcic also transformed from Prince Charming into an embittered ex.

He aided and inspired Bojan Pozar in writing his book, "Melania Trump – The Inside Story: The Potential First Lady," which reviewers have suggested is filled with vile gossip about Donald Trump's third wife (via Amazon). Moreover, Melania's lawyer, Natasha Pirc Musar, has suggested Zorcic's version of events is a fiction. "I invited him to my office. I asked him not to talk about [Melania]," said Musar, as per Telegrafi. "He admitted that they knew each other, but that they were never lovers." This was one rumored love story that had no happy ending. 

In Jackie Siegel's exclusive interview with The List, she wasn't afraid to spill the beans about her extraordinary life. However, she remained coy when she admitted to dating Donald Trump in an interview on HuffPost Live. "Kind of. We're friends... we're still friends now," she said. "We just went out a couple times. Like, he invited us to Mar-a-Lago and go to his parties and things like that. He's a really great person. So much charisma."

However, everything really changed for Jackie when she married Trump's fellow billionaire property mogul, David A. Siegel, in 2000. Until then, Jackie had been a beauty pageant queen, but she would, fittingly, go on to build a castle for herself. Jackie and her husband embarked on a building project that'd give Trump himself a run for his money in 2004, as they started work on their 90,000-square-foot mansion in Florida, stylistically inspired by France's 17th-century Palace of Versailles. However, it didn't exactly go to plan. The 2012 documentary "The Queen of Versailles," a moniker that Jackie uses as her Instagram handle, captured her travails during construction. But ten years after the documentary aired, the palace was still being constructed.

In January 2025, Jackie assured her followers the build was getting there, but sadly, in April of the same year, Seigel passed away after a battle with cancer. It's a very modern Sisyphean struggle, but the stoic Jackie has vowed to use the palace to raise money for cancer research (via WKMG News). Despite it all, she's come a long way from hanging out at Trump's Florida-based castle to building one of her own.