How Tiffany Trump's World Diverged From Her Famous Family

The Georgetown law student and first daughter went to Cannes this week with her boyfriend, seemingly enjoying the best of two privileged worlds

By Natalie Finn May 22, 2019 10:00 AMTags
Tiffany TrumpJustin Sullivan/Getty Images

Asked in October 2016 if she was interested in joining the family business one day, Tiffany Trump replied, "Of course I'm interested...but I'm applying to law school, though, so I like to bring a different kind of skill set to the company."

At this point, it certainly can't hurt to have a lawyer in the family. If Tiffany is still interested in the family business at all.

Raised by a single mom in California and then all of a sudden thrust into the he-has-five-kids spotlight when her father ran for president of the United States, Tiffany ended up the unwitting poster girl for privileged paternal neglect, the forgotten daughter next to favored princess Ivanka Trump. Two and a half years in, she remains a go-to punchline—not because of anything she has done, but mainly when comedians want to reiterate just how little they think of Donald Trump's family values.

But Tiffany isn't asking for anyone's pity.

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The 25-year-old Georgetown Law student and businessman boyfriend Michael Boulos were in the south of France where the 72nd Cannes Film Festival is taking place this week, photographed at the 5-star Hôtel Barrière Le Majestic, one of the spots frequented by celebs during the reliably decadent affair.

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While Ivanka can now only dream of the widely admired, relatively uncontroversial life she led before the 2016 election, Tiffany has managed to avoid that level of scrutiny precisely because, famous last name aside, she didn't grow up with her half-siblings in a gilded penthouse in Trump Tower. (For the brief period she did live there, the other kids were elsewhere with their mom.)

"Since I have grown up on the West Coast, I'm definitely different from all of them growing up on the East Coast," Tiffany told Oprah Winfrey in 2013. "It was great for me getting to grow up as a normal kid just out of the spotlight, versus all of them growing up in New York. They always had that intense media and spotlight on them."

Trump "would say that it's really a miracle that [Tiffany] is as well-adjusted as she is, and that she's accomplished anything," a Trump friend told Vanity Fair's Emily Jane Fox, author of the 2017 book Born Trump. "He gets that he screwed it up when it came to Tiffany, and this is a man who doesn't admit that he got it wrong on anything."

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Trump himself has acknowledged that he was always working throughout his kids' childhoods, and wasn't a particularly hands-on dad—for the older Trump kids or for now 13-year-old Barron Trump, his son with first lady Melania Trump. But true to form, Ivanka even quibbled with his modest estimation, telling ABC News' Barbara Walters in November 2015, "He was very available to us."

"Our times together," added Tiffany, by then posing as a full-time member of the fold, "we're learning, you know, playing in his office. He would always sneak me down to get a candy bar in the lobby." (Her mother's a health nut, so that would have been a very real treat.)

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Her mom, Marla Maples, married Trump in December 1993, when Tiffany was 2 months old. Howard Stern, O.J. Simpson and Rosie O'Donnell were among the 1,100 people who attended their wedding at the Plaza in New York.

The real estate tycoon had been through an impressively messy split with first wife Ivana Trump, the parents of three waging a tabloid war against each other via the New York Post (his) and New York Daily News (hers) before finally reaching a divorce settlement in 1990, in which Ivana got custody of Donald Trump Jr., Ivanka and Eric Trump.

Trump hadn't been planning to get married again, or have more children, at least not so soon.

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"I'm glad it happened," he said on The Howard Stern Show in 2004, per old tapes acquired by Newsweek. "I have a great little daughter, Tiffany. But, you know, at the time it was like, 'Excuse me, what happened?' And then I said, 'Well, what are we going to do about this?' [Marla] said, 'Are you serious? It's the most beautiful day of our lives.' I said, 'Oh, great.'"

Still, Trump called the New York Times 20 minutes after his fourth child was born at St. Mary's Hospital in Palm Beach, Fla., telling the reporter, "We have a perfect little girl, a combination in looks of both of us, to go with my three other wonderful children."

Tiffany, incidentally, is what he wanted to name his firstborn daughter, but Ivana wouldn't hear of it. "Everything involved with Trump Tower has been successful, and Trump Tower was built with Tiffany's air rights," he told the Times, referring to jeweler Tiffany & Co., which was next door on 5th Avenue. "But I've also always loved the name."

For her husband's 50th birthday, Marla commissioned an oil painting of Trump with all four of his children to replace one he had of just him with Don Jr., Ivanka and Eric that hung in his office. The new one featured little Tiffany sitting in Ivanka's lap.

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Trump and Maples separated in 1997 but were still technically married when Trump met future first lady Melania Knauss at a nightclub in 1998, the divorce taking years to figure out because Maples was contesting their prenuptial agreement (as Ivana did before her), which had promised her between $1 million and $5 million if they split up before reaching five years of marriage.

"It's a hard, painful, ugly tool," Trump later reflected to New York Magazine about prenups. "Believe me, there's nothing fun about it. But there comes a time when you have to say, 'Darling, I think you're magnificent, and I care for you deeply, but if things don't work out, this is what you're going to get.'" (He and Melania did sign one as well.)

Before the divorce was finalized in 1999 (reportedly for about $2 million plus child support), Maples, an actress, model and former beauty queen, relocated with Tiffany to California, where she scored the occasional acting job, but mainly juggled hosting gigs and embraced wellness and spirituality, eventually having her own radio show, Awakening With Marla.

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"We settled into a really beautiful life in Los Angeles where we went to church, the Kabbalah Center, school, soccer, basketball and everything for her to be able to live in a world where she would not necessarily be recognized as the daughter of Donald Trump and Marla Maples," Maples told Healthy Wealthy nWise.

"My goal for her was to let her do as I was longing to do; to find her own identity and her own self. We pulled away from that world in a big way and moved out to a suburb in Los Angeles. I cooked dinner five nights out of the week. The other two nights we loved sushi, so we'd be out having sushi. It was really all about getting that little girl to school every morning. I would get to the gym and do my workouts, and then my work would begin."

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Tiffany mainly visited with her dad (and future stepmom Melania) at Mar-a-Lago on her spring breaks, and occasionally in New York, while Trump would fly out to Los Angeles for important school events, or see her when he was in town on business.

"She'd like to get to know her father better and spend time with him like his other children did," Maples told the New York Times in 2016, "by going to his office and watching him work. Only now, he's not in the office anymore. He's on the campaign trail."

She added, "I had the blessing of raising her pretty much on my own." (Ivana Trump, too, has commented to that effect, that she raised the kids till they were 21 and then handed them off to their father and his business, the two inextricably linked.)

Tiffany has always been exceptionally close to her mom, telling Winfrey in 2013, "My friends are always like, 'Wow, you guys have a really good relationship.' She's with me a lot of the time and people find that kind of shocking."

On this past Mother's Day, Tiffany wrote on Instagram, which boasts numerous photos of her and Maples, "Thank you @itsmarlamaples for being there for me always and guiding me throughout my life! I wouldn't be where I am today without your unconditional love!"

"She's a great girl. She is full of a lot of love," Maples told Healthy Wealthy nWise about her then-15-year-old daughter in 2009. "Now she wants to start on her career path, so we're working on her music. She's starred in a couple of plays. She did a fantastic job. It's my career and it's her career, with a lot of loving times in between. She knows that's the core."

In her 2009 book The Trump Card (dedicated in part to Tiffany and Barron, "the next generation"), in an anecdote about how none of them took their family's wealth for granted, Ivanka recalled Tiffany coming to her for advice the previous Christmas about how to talk to their dad about acquiring some extra spending money—nothing too outrageous, Ivanka noted, just a raise in her allowance. Because she hadn't spent nearly as much time around their father as her other siblings had, Tiffany understandably hadn't benefited from Trump's largess as much, "just by virtue of lack of proximity."

Knowing Tiffany was nervous about asking, "Big Sis did an end-around to save Tiffany the trouble," Ivanka wrote. "I didn't tell her, of course, but I went to our father and suggested he think about surprising Tiffany with a credit card for Christmas, with a small monthly allowance on it. Sure enough, he did just that. Tiffany was thrilled and relieved. And appreciative."


Though not seeing her dad all that much meant she probably saw her siblings less, Tiffany was one of Ivanka's bridesmaids, along with Don Jr.'s then-wife Vanessa, when she married Jared Kushner in 2009. Ivanka also helped Tiffany get a summer internship at Vogue in 2015. 

"We would see each other on all of the holidays and talk to each other frequently," Ivanka told People in 2016. "She's my little sister! I've been close to Tiffany her whole life, and I really love her." But she paid Tiffany the ultimate Trump compliment while talking to the New York Times: "Tiffany has always been a very special person, very confident, very driven, always the hardest worker and not bashful about it. A lot of people are happy to get by without doing a lot of work, or work hard and pretend they don't. She is proud of her work."

For Big Sis' birthday last fall, Tiffany wrote on Instagram (a few days later), "Wishing my big sister and best friend a happy birthday (sorry for the late post, but you know my law school life haha) I love you so much!"

Tiffany may have inherited the performance gene from her momshe recorded a dance-pop tune in 2011 called "Like a Bird" with rapper Logiq and once told Oprah she was considering pursuing music as a career—but after graduation from the private Viewpoint School in Calabasas, Calif., she chose to attend her father's alma mater, the University of Pennsylvania.

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She started college in 2012, just as her father, who had become more famous than ever as host of The Apprentice, started publicly questioning whether or not President Barack Obama was really born in the United States. Dad becoming what's known as a "birther" didn't do anything to help the Trump name on the Ivy League campus, but Tiffany's spot in her privileged social circle—her group of friends was nicknamed the "Snap Pack" for all the chronicling they did of their highbrow exploits on social media—was not threatened.

She never appeared on her dad's reality show, but she and her friends were approached about doing their own. "It's easy money..." Tiffany commented to DuJour in explaining why they never accepted the offer. "But," interjected her pal Gaïa Jacquet-Marisse (great-great granddaughter of artist Henri Matisse), "it conflicts so much with all of our different personal goals. Besides, it's not about money or fame. It's about our friendships. It's about us being f--king amazing people and loving each other."

Tiffany graduated from Penn in 2016 with degrees in Sociology, concentrating in Law & Society, and Urban Studies.

By then, the ducklings had fallen into line.

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"He's true to himself and he speaks in a way that the average person can understand," Tiffany told Barbara Walters in 2015 when Walters asked Trump's four adult children if their dad had said—during what was then only five months on the campaign trail—anything that had made them cringe. "I think that's refreshing for everyone." (Eric Trump had immediately answered, "Truthfully, no.") 

The least talked-about Trump child told Walters, "It's all I know. I'm so happy to be Tiffany Trump. I'm so happy to be, you know, in the family I'm in, with my siblings and my father and my mother."

Melania gave only a handful of interviews before (and since) the election. As the campaign got increasingly ugly, it was left largely to Ivanka, Don Jr. and Eric to talk to the press, much of which involved defending whatever their father had said or tweeted on any given day.

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But Tiffany did join all of them in giving a solo speech at the Republican National Convention in July 2016 in Cleveland. She didn't have all that many applicable warm and fuzzy anecdotes to share, but she said her father used to write "sweet notes" on her report cards, and she had kept them all.

In an email to the New York Times in October 2016, when asked about his younger daughter, Trump wrote, "Tiffany is a tremendous young woman with a big and beautiful heart. She was always a great student and a very popular person no matter where she went. I am incredibly proud of Tiffany and how well she has done."

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In the meantime, Tiffany's mom praised her daughter for the way in which she was handling being in the public eye.

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"She is able to step in there and be her true self who loves her mother and her father and her family," Maples told People in the spring of 2016, while she was competing on Dancing With the Stars.

"Having raised her, I knew she would ultimately have a public life. But watching her sit there in that arena [during a recent Trump Town Hall] with that much pressure on her and see how the love we have shared through the years has shaped her. She has become a woman. I could not have been more proud of her."

And then, unexpectedly for most, Trump won the election, and Tiffany became a first daughter—just like Ivanka, only without the heavy expectations and, therefore, without all the blowback from Trump critics.

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Marla, who also attended the nominating convention in the summer of 2016, was in Washington D.C. to support Tiffany during all the inauguration festivities, the surprise culmination of the interminable presidential race, and where she shared spotlight after spotlight with her siblings. Tiffany, perhaps because she was with a boyfriend and not a spouse, stayed the night after the Jan. 20 inauguration ball at Trump International Hotel in D.C., rather than at the White House with everybody else.

The inauguration was on a Friday, and by Sunday everyone except for Ivanka and Jared, who had already moved to Washington, went back to New York. That included Melania, who stayed with Barron at Trump Tower until his school year ended before moving into the White House full-time.

Meanwhile, like her siblings, Tiffany has had a Secret Service detail since before the election, albeit a smaller one than father of five Don Jr. and mother of three Ivanka.

A patron of trendy East Hampton café the Golden Pear told Born Trump author Emily Jane Fox that, compared to how customers reacted when Chelsea Clinton walked in one day with her detail in the 1990s, Tiffany showing up with her boyfriend in May 2017 was a nonevent.


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"The world basically stopped" when Chelsea was there, the customer said. "For Tiffany, no one really noticed, and the people who did were intentionally looking the opposite direction." Someone approached to ask if he could use an extra chair at her table, and not even her security blinked. 

To this day, Tiffany and Barron's code names remain unreported, while Ivanka, Don Jr. and Eric are, respectively, Marvel, Mountaineer and Marksman. Melania is Muse.

But since it's impossible for the first lady or other first daughter to do anything normal out in public, shouldn't Tiffany be relieved that she can more or less do as she pleases?

Last summer, for instance, she went to London and then hung out with Lindsay Lohan in Mykonos, where the Mean Girls star was getting her MTV reality show Lindsay Lohan's Beach Club off the ground. (Lohan, incidentally, has been more complimentary toward Tiffany's father than some, tweeting in July 2017, "THIS IS our president. Stop #bullying him & start trusting him. Thank you personally for supporting #THEUSthat people should support their president.")


Tiffany and Boulos, whom she reportedly met in Greece, also vacationed earlier this year in Phuket and, this week, she looked to be living her best life in Cannes.

"Tiffany is happy she has so far been able to keep things with Michael under the radar," a source told Page Six in November about her relationship with Boulos, who is of Lebanese descent and grew up in Lagos, Nigeria, where his wealthy family does business. "But she introduced him to her family at Thanksgiving, and he comes across as a very intelligent young man from a great family. There was no mention of the president's unfortunate comment about African nations."

As a student at Georgetown Law, one who longingly posts throwback pics from her summer vacation while hunkered down at the library, just like anybody else would, Tiffany once again lives near her dad and certainly seems to be making the most of the proximity. On Instagram she posted photos of herself and Boulos in front of the Christmas tree in the White House's Red Room and visiting Mar-a-Lago for Easter.

Jean-Paul Aussenard/WireImage

Tiffany told People in 2017, "I think regardless of distance, I don't think that dictates any relationship strains. I really have an emotional bond with him and he was always just the funniest, most loving father."

But in April 2018, insiders told People that Tiffany, after growing closer to her father on the campaign trail, once again felt like a second-tier Trump kid.

"Since the inauguration, Tiffany and her father have sometimes gone for months without speaking and she went a very long time without seeing him," a source close to her said. "The last time she was at a family function with him, it was awkward for her and she didn't feel totally welcome." (The White House didn't comment.)

Another source said that their relationship wasn't bad, it was just different than his connection with the other kids, due mainly to her growing up on the opposite side of the country.

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And just as people have wondered about Melania and Ivanka's true political leanings—not as much lately, but a lot at first—Tiffany has been the subject of the same sort of speculation. Her date to Trump's inauguration was then-boyfriend Ross Mechanic, a registered Democrat who she met at Penn—and whose real-estate attorney father donated thousands to Hillary Clinton's presidential campaign, according to the New York Daily News.

They dated for two years before breaking up toward the end of 2017, when she moved to D.C. for law school. A source insisted to Page Six that it was a geographical, rather than a political, issue, noting that Mechanic lived in New York.

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And though she can buy an iced coffee without causing a stir, it did not go unnoticed when Tiffany "liked" an Instagram post featuring several photos from the March for Our Lives rally for gun control in D.C. last year, with the caption, "Next massacre will be the GOP in the midterm elections." And at the State of the Union in February, her all-white ensemble prompted speculation that she was dressed in solidarity with the sea of Democratic congresswomen also wearing white.

But Tiffany wears white a lot, and she has been careful to not actually say or tweet anything that contradicts what her family seems to stand for these days. Her "I just voted" post in 2016 included the hashtag "#TrumpTrain" as one might expect, but even in 2014 she tagged a voting post with "@pennvotered," seemingly a nod to voting Republican. 

Late last year, she shared a photo on Instagram Story of herself and a friend checking out the game Trumped Up Cards—a Cards Against Humanity-style word-association game "For People With Big Hands"—at a Georgetown bar. And while that raised some eyebrows among those hoping for a sign of anti-Trump life in the universe, she may as well have been wearing a jacket that said, "I really don't care, do u?"