Tiffany and the Trumps: Insiders describe how the president's younger daughter has charted what they say is a distant relationship with her father and come to terms with having America's most divisive last name

  • Tiffany Trump has long been depicted by the media as the president's "other daughter."
  • Business Insider spoke with 12 of Tiffany's classmates, friends, and biographers to chart her relationship with her last name and her father.
  • They revealed a young woman who grew up shielded from the spotlight and whose life is divided into two periods: before and after the 2016 election.
  • While she tried to keep a low profile during her college years, she fell into the public eye after she hit the New York City socialite scene and her father hit the White House, garnering criticism from the public and media along the way.
  • Tiffany has been involved in the last few weeks of the 2020 election. Her next steps may depend on whether President Trump is reelected.
  • Visit Business Insider's homepage for more stories.

On August 25, a polished young woman in a baby-blue pantsuit and smoky eye makeup stepped onstage at the Republican National Convention in Charlotte, North Carolina. She was 26 and had just finished at Georgetown Law, and she was about to address America in her second RNC speech.

"Like so many students across the world, I graduated from law school during the pandemic," she said. "As a recent graduate, I can relate to so many of you who might be looking for a job."

The young woman in question was Tiffany Trump, the youngest daughter of President Donald Trump, and her words elicited backlash from critics who found it disconnected from reality.

The criticism she faced after the speech was far from the first time Tiffany had faced scrutiny from the general public and the media alike. She's been caricatured on "Saturday Night Live." Her 2016 RNC address (her first time addressing the RNC) was widely seen as a poor attempt at humanizing her father. And reports have long told a narrative of Tiffany — the child of Trump's affair turned second marriage with the actress Marla Maples — as the "other daughter," second to Ivanka in Trump's eyes and an outcast among his three children with first wife, Ivana. Tiffany has often felt hurt by this media portrayal, Maples told The New York Times in 2016.

One of Tiffany's University of Pennsylvania sorority sisters said Tiffany has shouldered the pressure well. "She's done a really great job of not letting those opinions faze her so much, in light of all the negativity," she said.

Gwenda Blair, the biographer behind the 2000 biography "The Trumps," said Trump had a closer relationship with his three children with Ivana than he did with Tiffany, but she disagreed with the media's interpretation of Tiffany as the forgotten child. Instead, Blair said she believes it comes down to a matter of brand.

"I don't think she's part of the brand," Blair told Business Insider. "And for Donald Trump, the brand Trump is everything."

With the upcoming election now just days away, Business Insider spoke with a dozen of Tiffany's classmates, sorority sisters, and friends, as well as two Trump family biographers, to figure out just what Tiffany's brand is. Many requested anonymity for privacy reasons during a turbulent political climate. The big question: How has Tiffany's relationship with her famous last name evolved since her father became president?

What we found was a young woman who grew up deliberately shielded from the spotlight but whose life, sources said, is divided into a period before the 2016 election and a distinctly different stage after the 2016 election. Multiple people who knew Tiffany at UPenn and Georgetown all said she kept a low profile on campus; nine used the word "humble" when describing her to Business Insider. By the time Trump hit the White House, Tiffany — who had already become a staple of the New York City socialite scene — increasingly became press fodder. However, the increased media coverage did not come with a solidified spot in America's first family. Even now, while her newly earned Georgetown degree makes her the only Trump offspring with a law degree, various sources said she still struggles to find her footing within the powerful family.

Tiffany and the White House did not respond to multiple requests for an interview.

Growing up Trump — kind of

Tiffany was named after Manhattan's iconic Tiffany & Co. flagship store, which is adjacent to Trump Tower, but she was born in West Palm Beach, Florida. After Trump and Maples divorced in 1999, Maples and Tiffany, then 5, moved across the country to Calabasas, California, home to celebrities like the Kardashians and Drake.

Growing up far from the Trump mecca of New York City, Tiffany's childhood was largely shielded from the press. Maples, a single mother, raised Tiffany with home-cooked meals and "Gilmore Girls" marathons. Tiffany attended the Viewpoint School, a K-12 school that today charges up to $43,900 in annual tuition. Maples didn't respond to multiple requests from Business Insider for an interview.

In a 2016 interview with People, Tiffany said Maples gave her space to be her own person: "She moved us out of New York to get out of the spotlight and let me grow up and find my own identity versus being in the shadow of a name or growing up very young with all that pressure. She wanted me to have a chance to have a normal childhood."

"She wasn't, like, wild or [into] parties or anything growing up," a close family friend who spoke on condition of anonymity for privacy reasons told Business Insider of Tiffany's California days. "Regardless of who her friends were, she was always shy and more timid."

While growing up in California may have afforded her a shot at a normal childhood, it also meant that she was left out of the family business and far from her father.

Trump, then busy expanding his real-estate empire and transitioning into a TV personality with "The Apprentice" in 2004, wasn't there with "day-to-day skills as a parent," Maples told People.

She said she encouraged Tiffany to forge her own relationship with Trump, taking her to the city a couple times a year to see him.

"I don't know what it's like to have a typical father figure," Tiffany previously told DuJour. "He's not the dad who's going to take me to the beach and go swimming, but he's such a motivational person." 

The UPenn era: Just another high-profile name

On a rainy day during UPenn's sorority rush week in 2013, a tall blonde with a heart-shaped face invited a fellow rushee (a college student interested in joining a sorority) to stand under her umbrella.

The rushee, who spoke on condition of anonymity for privacy reasons, told Business Insider she had no idea that person was Tiffany. 

"She was so sweet and we just started talking," she said. Both of them joined Kappa Alpha Theta, which has a national star-studded list of alumni including former first lady Laura Bush, Sen. Elizabeth Warren, and the fashion designer Tory Burch.

It was sophomore year for Tiffany, who enrolled in her father's alma mater in 2012 to study sociology with a specialization in law and society. At the time, Trump was best-known as a real-estate mogul and the "you're fired" guy from "The Apprentice," which was in its 12th season.

A post shared by Tiffany Ariana Trump 𝒯. 𝒜. 𝒯 (@tiffanytrump)

 

It was at UPenn that Trump — already a prominent figure in American media — became a more prominent figure in Tiffany's life, the close family friend said: "I think she was excited to have a father figure and to work hard and go to an Ivy League school." When Tiffany graduated in 2016, her father attended the ceremony amid his presidential campaign. 

Despite her more involved relationship with her famous father, three people close to Tiffany in her UPenn years said she was still able to maintain a relatively low profile. They also described Tiffany as a staple at sorority events who made friends easily. "She's totally normal and very down to earth," a former UPenn classmate told Business Insider.

The classmate said most people didn't perceive Tiffany as merely her last name. Two students who attended UPenn at the same time Tiffany did, including the classmate, said it also wasn't unusual to see celebrity offspring around campus.

"People weren't put off by the fact there were celebrities around because that's what happens when you go to a school where there's a lot of money floating around," the classmate said.

Friends said Tiffany, who lived off campus, mostly hung out with her sorority sisters, but she did befriend other notable names on campus like Naomi Biden, Democratic presidential nominee Joe Biden's granddaughter. Naomi Biden did not respond to Business Insider's request for comment.

However, the UPenn rushee said the pressure of being a Trump didn't leave Tiffany unscathed. "It was really important to her to build her own path," the rushee said. "I think that she had a lot of pressure from her family and people's perceptions of her."

A post shared by Tiffany Ariana Trump 𝒯. 𝒜. 𝒯 (@tiffanytrump)

 

Some students were more caught up in the Trump name than others, and various sources said Tiffany tried to shy away from the increasingly inevitable limelight that came with being a Trump. Maddy Penn, Tiffany's sorority sister, described a time she and Tiffany went to a frat party, only to find themselves surrounded by whispers that Tiffany was in attendance. In an effort to avoid that kind of attention, Penn said, she and Tiffany often hung out more with international students who weren't as conscious of the last name Trump.

"She keeps her good friends really close," Penn said. "The rest is compartmentalizing, letting things roll off her back. She has a very, very thick skin."

The turning point: politics and the NYC crowd

By the mid-2010s, the low-key presence that acquaintances and friends described Tiffany as having cultivated on campus began to slowly slide into the public eye off campus.

In 2014, while she was still an undergraduate student at UPenn, the close family friend said Tiffany moved to NYC. She became a more prominent fixture in the social scene and started attending fashion shows, the friend added. 

"That's when her lifestyle changed," they said. "She wasn't really embracing her name before." 

Page Six welcomed her to its gossip columns after she was spotted at Manhattan's Boom Boom Room for a Halloween party, and she was photographed by Getty at Heidi Klum's annual Halloween party and the Millennial Ball with fellow socialites. 

Tiffany ran with the Snap Pack, a group of wealthy young New York socialites, rubbing elbows with the likes of Gaïa Jacquet-Matisse, the great-great-granddaughter of Henri Matisse, and Kyra Kennedy, the great-niece of former President John F. Kennedy. They often appeared on the "Rich Kids of Instagram" account, and Tiffany's own Instagram account began featuring images from vacations on Greek islands and in the Hamptons. Despite a bigger foothold in the social scene, Tiffany was still flying under the radar. There was yet to be a "Tiffany Trump" Wikipedia page in 2015.

That all changed when 2016 rolled around — the same year Tiffany graduated from UPenn and Trump was elected president. By this point, Tiffany had cultivated a reputation as "Instagram famous," with 156,000 followers (today, it's 1.3 million). Articles in The New York Times and Cosmopolitan started to explore the enigma of a low-profile Trump. Suddenly, she wasn't on campus much, the UPenn classmate said.

Tiffany was largely absent from the campaign trail and had difficulty adjusting to campaign life, The Times said, but she made some early appearances, including a 2015 family interview with Barbara Walters. Her speech at the July 2016 Republican National Convention was a political debut of sorts, where she painted a glowing picture of her father, saying, "He's always helped me be the best version of myself."  

Michael D'Antonio, the author of the 2015 biography "The Truth About Trump," points to the 2016 election as a turning point in Tiffany's life. Before that year, he said, the last name Trump hadn't always carried a stigma, but his campaign became such a "destructive force" that it changed Tiffany's relatively normal life.

"She was devoted to trying to figure out how to do it her way … even though people associated her as more myth than actual human," he said of pre-2016 Tiffany. "And I think her work at times to sort that out for herself as a young adult was interrupted by this tidal wave of publicity and conflict."

He added: "She can't really be that person ever again. It's really hard not to be forced into this role with so little power to separate from the name. And it's created an identity that is very unfair."

The Georgetown era: black cars and baseball caps

In 2017, Tiffany enrolled in Georgetown University, just 10 minutes from the White House, to study criminal justice reform and tech and cyber national security. This time, the Secret Service was in tow.

"You knew Tiffany was there if you saw all these big black fancy cars in the parking lot," a fellow Georgetown classmate, who spoke on condition of anonymity for privacy reasons, said. They added that sometimes when they arrived at class early, a Secret Service agent would be casing the room. Several students said the agent would sit next to Tiffany in class and accompany her around campus.

"It was like this 45-year-old man who's wearing a hoodie, Georgetown ball cap, trying to pretend to be a student, but he has an earpiece and a gun," the fellow Georgetown classmate said.

1st day of Law School ✔️ #GeorgetownLaw ⚖️👩🏼‍⚖️

A post shared byTiffany Ariana Trump 𝒯. 𝒜. 𝒯 (@tiffanytrump) on Aug 28, 2017 at 9:37pm PDT

 

Overall, Tiffany and the Secret Service created "no big footprint and no disruption," another law student said. She didn't hang around campus much and often left after class. While her presence initially generated buzz, multiple students said, it quickly died down.

The Georgetown classmate did say Tiffany seemed highly conscious of her profile: "She definitely had this air of like, 'Everybody's thinking about me, and Everybody's wondering what I'm going to do.'"

She was a copresident of the Cyberlaw Society and spent her vacation breaks as professor Shon Hopwood's research assistant for criminal-justice law reform. This helped her influence her father's policies: She had a role in the First Step Act, a bill for prison and sentencing reform that Trump signed and which helped pardon the first nonviolent offender released under the act, Washingtonian reported. Hopwood did not respond to Business Insider's request for comment.

Business Insider reached out to multiple Georgetown professors, who either declined to speak or didn't respond to an interview request. "We cannot speak to you about her," one professor told Business Insider.

Six people who knew Tiffany at UPenn or Georgetown described Tiffany as hard-working and studious, known for pulling all-nighters. But the Georgetown classmate said they felt Tiffany wasn't taking school as seriously as the rest. 

"The stakes just weren't as high for her," they said. "I think some people resented her for that."

Tiffany kept up occasional social appearances during her studies, including fashion shows and official family appearances, like the White House Christmas tree-lighting ceremony.

But some students scrutinized Tiffany's political beliefs. The former Georgetown classmate said students would challenge Tiffany on her father's policies. At the time, they said, Trump was pushing for new immigration laws — a major point of contention among students. 

"She would just say, 'I understand what you're saying, and I just hope that we can move on,'" they added. "She was very diplomatic in that way."

Tiffany graduated virtually in May. Her father invited her to the White House to celebrate, CNN reported.

Struggling to fit into the family identity

While Tiffany shares a last name with America's first family, various reports and sources indicate that she's still not fully seen as part of the innermost family. At least one of Tiffany's acquaintances attributed this difference to her California upbringing.

"There's a sense she's very different from the rest of her family because she grew up in California and was sort of separate from the Trump business," the Georgetown classmate said. "All the other Trump kids are very East Coast prep school, and she's very West Coast beach vibe."

D'Antonio, the biographer, said Tiffany may have struggled to adapt to her father's expectations of his family members.

"I think that who Donald really is in relation to his family members is exploitive and demanding," D'Antonio said. "He has these expectations that everyone exists to serve him. The way people look and sound and move is of utmost importance. It actually matters more than character. And he wants everyone to fit that mold. And I don't think that Tiffany fit into it very comfortably."

Blair, the biographer behind "The Trumps," said Tiffany seemed like the odd person out because she wasn't prepared for the limelight the way her siblings were. 

"She seems like this mystery figure who, for better or worse, didn't get the same kind of preparation as the three older children," Blair said. "The public role ended up being thrust upon her." 

To 2020 and beyond

Unlike Trump's other three adult children — Ivanka, Eric, and Donald Jr. — Tiffany wasn't named to her father's transition team during the 2016 campaign. Politico also wrote in September that Tiffany wasn't expected to play a role in Trump's reelection campaign apart from occasional appearances.

As in the 2016 election, Tiffany's role in Trump's campaign has been sporadic compared with her older siblings' roles. But while Tiffany's key appearance in 2016 was at the RNC, Blair said Tiffany has been a little more involved this year, making a handful of appearances in the final weeks of the election. In addition to speaking at the 2020 RNC, she also spoke at a "Trump Pride" event and has hit the campaign trail everywhere from North Carolina to Michigan.

D'Antonio described Tiffany's involvement in the campaign as a last-ditch effort on Trump's part. He likened the position Trump puts Tiffany in to the captain of the Titanic sending an officer down to the boiler room to rescue those trying to keep the ship afloat. 

"This is an impossible mission," he said. "But if she is to be part of the family, she doesn't have much choice."

Blair said Tiffany's increased involvement in Trump's campaign was likely tied to her maturity. "She's four years older. She's more experienced and presumably would be able to do a more complete job," Blair said.

The close family friend highlighted more changes in Tiffany beyond just the usual growing up process, however.

"She's changed a little bit in the past three years," the close family friend said. They said Tiffany had always been more shy and timid, which came across in the 2016 RNC speech to them. But she seemed different at the 2020 RNC, they said, adding, "She's kind of taken on her father's tendencies and thinking process." 

D'Antonio said he believed Tiffany has tried to toe the line between being as ethical as she can, while accommodating her father. She's indicated support for liberal social issues, liking Instagram posts supporting gun control; posting a black square on #BlackoutTuesday (a social-media movement subsequently decried by some leading activists as a form of "social-media slacktivism" that created more harm than good), the only Trump to do so; and celebrating Pride day. 

A Trump biographer thinks Tiffany can find a seat in Trump's circle after graduation, whether or not he's re-elected.SAUL LOEB/AFP/Getty Images

But D'Antonio said that at the recent Trump Pride event, Tiffany crossed a line in saying that Trump was supportive of the LGBTQ community. Critics said the speech was hypocritical based on actions from the Trump administration and called her out for not saying the "T" in "LGBTQ."

Tiffany hasn't yet commented publicly on her next career move, and friends told Business Insider they didn't know what her next step would be. The Georgetown classmate said Tiffany once told them she didn't plan to be a lawyer. Tiffany said in a 2016 ABC interview that she was interested in joining the family business but hoped to bring a different skill set to the table. 

If Trump is reelected, Blair thinks there's a chance Tiffany could become another White House advisor or have a more specific role in a second Trump administration, she said. And if he loses, she thinks Tiffany still might find a seat in her father's circle.

She said, "There will be a place for her in Trumpworld."

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