The Truth About Tiffany Trump's Relationship With Her Brothers

The bond between sisters is a strong one. That's why most of what we've heard about Tiffany Trump's relationship with her siblings, who grew on another coast, have been about her and Ivanka Trump. But the youngest Trump daughter and Georgetown Law grad has two older brothers too, as well as a younger brother in Barron Trump. So what do we know about Tiffany's relationship with her brothers? 

Tiffany has been photographed in public with her brothers more than ever before since their father moved into the White House. But are they friends? Do they fight all the time? Do they draw imaginary lines in the back of Air Force One and say, "Whatever you put on this side of the line is MINE!" We took a look at the times Tiffany and her brothers have crossed paths in the media and found the siblings may get along better than some people think.

Donald Trump has five children from three different wives. Don Jr., Eric, and Ivanka share a mother in Ivana Trump, and grew up with her and Donald in New York City. Baron is Donald's son with Melania Trump. Tiffany Trump, however, is the daughter of Marla Maples, Donald Sr.'s former mistress-turned-wife, who scandalously ended his marriage to Ivana Trump. Donald Sr. and Marla Maples were divorced in 1999, and Maples moved with their daughter, Tiffany, to Calabasas, Calif.

While Donald Sr. paid $650,000 a year to Ivana in child support, he paid only $100,000 to Maples, who also got $1 million herself and $1 million for a house as per her prenuptial agreement, according to Vanity Fair. Still, mother and daughter lived comfortably in Calabasas, a town you may also know as home to the Kardashians. Though a People profile quoted Tiffany as saying she knew them "like a little bit," the story went on to say she and Kendall Jenner were the same age and had several mutual friends. Celebrity friends or not, it made getting to know her siblings difficult and, if nothing else, created a highly distanced relationship.

The Trumps are not the first family to squabble over a big inheritance, but they might be the first one to have it discussed on The Howard Stern Show. When Donald Trump appeared on the shock jock's program back in 2005, host Howard Stern asked him if his kids were trying to "bump off" Tiffany Trump, according to tapes obtained by Newsweek.

Donald dodged the question until Stern finally cornered him, as noted by People, saying, "Tell the truth, though." Donald responded, "Yes." Earlier in the interview, Donald made the point that every time he has another child the inheritance goes down by 20 percent, so, of course, his kids would get upset. Only Donald Jr. and Ivanka were mentioned during the interview, so no word on if Eric had tried to have his younger sister disinherited. Donald did deny, however, that Tiffany had put a "hit" out on Melania Trump's then-unborn baby, Barron. Though Donald did say, "Well, you know, it does cut up the pie as you keep producing." Which might imply some financially induced resentment from Tiffany's older brothers.

For some families, traditions are holiday dinners and summers at a lake cabin. For the Trumps, tradition means attending a prestigious Ivy League university. Donald Trump Sr. graduated from the University of Pennsylvania's Wharton School in 1968, a fact he mentioned no fewer than 52 times in speeches between 2015 and 2018, according to the Daily Pennsylvanian, the school's official newspaper.

Donald Trump Jr. also graduated from the Wharton School, where, according to People, he had a reputation for hard partying and drinking. Similarly, Ivanka Trump graduated from Penn. So it was no huge surprise when Tiffany Trump opted for Philadelphia's premier private school, despite living on the West Coast. After graduating with a double BA in sociology and urban studies, according to Vogue, she opted to attend law school at Georgetown University in Washington, D.C. Georgetown, not coincidentally, is the alma mater of older brother Eric Trump (via Washingtonian). 

Long before Tiffany Trump's day-drinking 27th birthday escapade in Miami made Page Six headlines, her reputation for enjoying adult beverages during the daylight was comic fodder. At least it was for her brother Eric Trump, who appeared on Fox News in 2019 to defend a lawsuit his family had filed to stop a congressional subpoena of Trump family financial records.

Eric said the request was overreaching and an invasion of privacy, claiming congress was asking for trivial things like his bank records and documentation of how much his wife spent on baby formula. But Eric insisted the prying wasn't limited to himself. "I want to know how many beers Tiffany had on Friday afternoon in Georgetown," People reported Eric saying, jesting at the ridiculousness of Congress' requests. "I mean, these are literally the things they're asking for."

In May 2020, Tiffany graduated Georgetown University, where she was a student at the time of the interview. No record of a congressional request for her bar tabs has been confirmed, and the joke may be more of a dig at Congress than his little sister's drinking habits. Still, we wonder how she felt about them.

In October 2020, Saturday Night Live's "Weekend Update" segment welcomed "special guests" Eric Trump and Donald Trump Jr., played by Alex Moffatt and Mikey Day. In an effort to show the Trump family's unified front, the characters invited their sister to join them on stage. But because Ivanka Trump "doesn't like us," as Eric interrupted, they had to settle for Tiffany Trump instead.

Chloe Fineman rolled onstage as Tiffany, donning a sailor's hat and bringing a champagne bottle to mock Tiff's headline-making Miami birthday soiree (via Page Six). She cracked a few jokes about partying without a mask and how stepchildren named Tiffany are supposed to get drunk in South Beach. "Don, who is that lady?" Eric asked his brother. Don Jr. informed his brother it was Tiffany, before realizing, "I don't know if you and Eric have officially met." Tiffany responded, "Not in person, no."

Though the sketch was obviously satirical, it demonstrated that the Trump brothers may not take Tiffany as seriously as they do their other sister — at least, that's how it may appear to those on the outside looking in. Even if they don't, as the sketch implied, call her "Not-Vanka."

Though her brothers didn't necessarily flock back to New York to work in the Trump real estate empire after college, Tiffany Trump has shown interest in joining the family business. Donald Trump Jr., according to Vanity Fair, moved out to Colorado and lived out of the back of a truck before returning to New York in 2001 to join the Trump Organization. He and brother Eric Trump now head the business. And Tiffany may be joining them sooner rather than later. 

During a 2016 interview with ABC News, which the older Trump brothers were also part of, George Stephanopoulos asked Tiffany if she was planning to work with her family. She responded, "Of course, I'm interested. I think — I'm applying to law school though so I like to bring — a different kinda skill set to the company."

President Donald Trump seems excited at the prospect. "Just what I need is a lawyer in the family," he jokingly tweeted out when congratulating Tiffany on her Georgetown Law graduation in May 2020. With all of them working together, perhaps Tiffany and her brothers can forge the relationship they never had growing up.

Though some may have perceived hostility between Tiffany Trump and her brothers, the younger Trump sister insists it's more a matter of growing up thousands of miles away from her siblings.

"Since I have grown up on the West Coast, I'm definitely different from all of them growing up on the East Coast," she told Oprah Winfrey in 2013 (via E! News). She went on to say she was grateful for growing up far from the media spotlight that followed her siblings in New York, describing herself as a "normal kid."

A People profile backed her up, citing a source close to the family as saying there wasn't really a rift between Tiffany and her siblings. Rather, the insider claimed there was a "separation of time and distance" because Tiffany grew up in a different time zone. But the same source admitted she was not as "intimately involved with the family dynamic" as her siblings, which may further the perception of Tiffany as an outcast.

During a 2016 60 Minutes interview with the Trump family, the elder children had clearly defined roles as members of the Trump transition team, whereas Tiffany Trump didn't say much. But the Trump kids would contribute toward their father's 2020 reelection bid years later. All the adult Trump children gave speeches at 2020's Republican National Convention, but outside the RNC, they've had decidedly different styles of campaigning for their dad. 

The tune was a little different by 2020, though, when Tiffany received great praise from some in the conservative media. The Washington Examiner trumpeted, "Tiffany Trump makes a much better case for the president than her brothers do" after her RNC speech. The Examiner pointed to Tiffany's appeal to women, especially suburban women from places like Calabasas, as far more relatable than her older brothers. And while the elder Trumps' speeches "fanned the flames of the culture war," Tiffany focused on the president's accomplishments and American values. This, the paper said, gave her wider appeal for those outside Donald Trump's traditional base. This may signal a greater role for Tiffany moving forward and, possibly, working more closely with her older brothers.

At the time of this writing, Tiffany Trump is dating Michael Boulos. He is a wealthy Nigerian heir whom she met on a Greek escapade, according to Page Six. The same story said that things were going so well with Boulos that Tiffany brought him to Mar-a-Lago for Thanksgiving in 2018, and introduced him to the whole Trump clan at the estate.

A source told the tabloid, "She introduced him to her family at Thanksgiving, and he comes across as a very intelligent young man from a great family." Though neither Donald Jr. nor Eric has commented publicly on their opinion of Tiffany's boyfriend, Boulos posted a picture on Instagram in February 2020, showing himself with the Trump family at the U.S. Capitol. In the photo, the four eldest Trump children posed with their significant others at the State of the Union speech, showing they attend events together and are familiar with the important people in each others' lives.

A 2018 People profile told the story of Tiffany Trump growing up in Calabasas, Calif., with only limited opportunities to visit her older siblings in New York. But as she's gotten older, Tiffany spends more time at Mar-a-Lago and at the White House. This also means more time with her brothers Eric and Donald Jr. In 2018, Page Six reported her spending Thanksgiving in Palm Beach with her family, introducing her new boyfriend during the holidays.

"Tiffany goes to the White House for holidays," an unnamed source said in the People profile. It went on to detail Tiffany's holiday trips since her father assumed the presidency, including Easter egg rolls, family dinners, tree-lighting ceremonies, and turkey pardoning. It painted them all as family affairs, where Tiffany was fully included. Most notably, Tiffany spent Christmas 2017 at Mar-a-Lago, where she controversially tweeted a video of herself and sister Ivanka lounging by the pool in bikinis. While people may not have liked seeing the first daughters in swimsuits, at least the two were spending quality time together! Hopefully, Tiffany and her brothers hung out too.

The Trump children have appeared in a number of interviews together, and while Eric Trump and Donald Trump Jr. take up much of the air time, Tiffany Trump doesn't get too many words in. During a 2016 post-election 60 Minutes interview, she made one comment about how she felt after her father's election and only after prompted by Lesley Stahl. Ditto for a 2016 interview with Sean Hannity, during which Tiffany finally spoke up at the end, saying, "It's hard but we know who our father is, and I think no tabloid can write anything that will make us doubt that."

Perhaps Tiffany's most telling group interview, however, came in a 2015 interview with Barbara Walters. When Walters asked if anything Donald Sr. said on the campaign trail made them "cringe," Eric answered with a quick, "Truthfully, no." Tiffany, on the other hand, had a more diplomatic answer, saying, "He's true to himself, and he speaks in a way that the average person can understand. I think that's refreshing for everyone." It shows Tiffany is not afraid to make her own statements separate from her brothers.

Body language experts took deep dives into how Tiffany Trump presented herself during her speech at the Republican National Convention in August 2020. But take a look at some of the snippets in the video, and you'll see Tiffany walking in behind her older brothers and just in front of younger brother Barron Trump.

Could they simply be lined up in order of age? Or does this formation say more? In an Elite Daily analysis of the Thanksgiving turkey pardoning ceremony, body language expert Dr. Lillian Glass remarked on Tiffany's tendency to stand in the back. Speaking of Tiffany's relationship with Ivanka Trump, Glass said, "There is genuine respect ... Tiffany stays in the background ... once again knowing she is not out front and center." This body language could translate to her body language with her brothers too, meaning she knows to stand back from them in official situations.

We've spent a lot of time here talking about Tiffany Trump's relationship with her older brothers Donald Trump Jr. and Eric Trump. But she also has a younger brother, Barron Trump, the only child of Melania and Donald Trump. They are closer in age than Tiffany is with her older brothers, but because Donald Trump's youngest son is not photographed nearly as much as the adult Trump kids, we don't know much about his relationship with Tiffany.

She did, at least, give him a happy birthday Instagram post in March 2020 when Barron turned 14. "Happy 14th birthday to the best 'little' brother I could ever ask for! You mean so much to me, Barron, I wish you all the happiness in the world! Love you!" she wrote. This may just be a caption, but it was thoughtful and shows they have a friendly relationship. Interestingly, Tiffany beat her father to the punch, as it were. The president reportedly hadn't yet publicly wished his son a happy birthday.