Inside Donald Trump's Relationship With His Youngest Daughter Tiffany

It's long been rumored that Donald Trump's favorite child is Ivanka Trump. As he constantly likes to remind us, Donald's relationship with Ivanka is special. Tall, blond, and glamorous, Ivanka has been the apple of her father's eye for years; the former president is seemingly in awe of his eldest daughter's beauty and, as he himself has said, would probably be dating her were it not for their shared DNA. As he waxes lyrical about his statuesque progeny, it's easy to forget that there's a second Trump daughter: Tiffany Trump.

For many years, it appeared that Tiffany was the overlooked Trump child. Even Donald Trump Jr., who seems stuck in the shadow of his father (Donald once lamented that his namesake could grow up to be a loser), seems to rank higher than Tiffany in the Trump family pecking order. He has, of course, been active in his father's political campaigns and is reportedly responsible for Donald's friendship with running mate J.D. Vance. And while his other kids were often photographed front and center with the Donald in family portraits, Tiffany was almost always relegated to background player. 

But with Tiffany making appearances at her dad's hush money trial and the 2024 Republican National Convention, it seems that she may be the forgotten daughter no more. Let's take a look inside Donald Trump's relationship with his youngest daughter, Tiffany Trump.

When Donald Trump's second wife, Marla Maples, revealed that she was pregnant with the couple's first child in 1993, the Donald wasn't exactly jumping for joy. Appearing on "The Howard Stern Show" (via Newsweek) in 2004, Donald discussed his odd — but arguably on-brand — reaction to the news. "You know, at the time it was like, 'Excuse me, what happened?'" he recalled. "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.'" Reading back on her dad's comments would undoubtedly leave Tiffany Trump (or any kid, for that matter) less than flattered. 

But when Tiffany, who was named after Tiffany & Co., was born, Donald appeared to have warmed to the idea of expanding his brood. He did, however, express his joy at having a second daughter in a rather bizarre way. During an appearance on "Lifestyles of the Rich and Famous" (via People) in 1994, Robin Leach asked Donald and Maples about their little bundle of joy, who was then a year old. "I think that she's got a lot of Marla, she's really a beautiful baby. She's got Marla's legs. We don't know whether or not she's got this part yet but time will tell," Donald said, referring to his wife's breasts. Truth be told, Donald has never been the best at describing his daughters' looks.

Though she was born into immense privilege, Tiffany Trump's life hasn't been free from tragedy. When she was just 5, her parents called it quits and she was raised solely by her mom, Marla Maples, in California. According to Maples, Donald Trump was a notably absent figure throughout Tiffany's childhood, providing ample financial support but little in the way of quality time. "Her daddy is a good provider with education and such, but as far as time, it was just me," Maples told People in 2016. "Her father wasn't able to be there with day-to-day skills as a parent. He loves his kids. There's no doubt. But everything was a bit of a negotiation."

Regardless, Maples wanted Tiffany to have a relationship with her father. Accordingly, she took her to Donald's office in New York a couple of times a year, where Tiffany would have dinner with her dad and his new wife, Melania Trump. But Tiffany resigned herself to the fact that Donald would never be a permanent fixture in her life, rather flitting in and out to offer words of fatherly wisdom. "I don't know what it's like to have a typical father figure," she told Du Jour. "He's not the dad who's going to take me to the beach and go swimming, but he's such a motivational person."

Tiffany Trump attended the $43,900-a-year Viewpoint School and had little contact with her father during this period. Writing in the Los Angeles Times, Tiffany's former classmate, Diana Delgado Cornejo, claimed that Donald Trump didn't show up to his daughter's school plays.

Despite his apparent absence from his daughter during her school days, Donald has made it clear that he is proud of Tiffany for her academic achievements. "She really is a terrific student, but more importantly, whenever we get the report card, the teachers write that she is the nicest person," Donald said, per the Daily Mail. "Every one of them say, 'Tiffany's marks are an A, but more importantly, she's one of the nicest students we've ever had.'" Tiffany reportedly saved all her report cards so she could be reminded of the sweet things her dad had to say about her.

When Tiffany began studying at the University of Pennsylvania in 2012, she had an opportunity to grow closer to her dad, who was living in nearby New York. "We see each other as much as possible and of course we speak on the phone," she told People in 2016. "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."

Growing up with the Trump family name hasn't always been easy for Tiffany Trump. Being the daughter of "The Apprentice" star reportedly led to her being bullied at school by her peers. As a teenager, she appeared more aligned with her mother and hoped to follow in her footsteps by becoming an actor, but soon she began to seek the approval of Donald Trump and enrolled in law school. "There are instances where demonstrating family loyalty — family love — means upholding a core identity around wealth," filmmaker Jamie Johnson, who made a documentary about the Trump kids, told The New York Times. "The more public the family, the greater the emotional responsibility to uphold the public image." Likewise, according to sources who spoke to Business Insider, Tiffany felt pressured as a Trump progeny to excel, but was insistent on forging her own path in life.

But by the mid 2010s, Tiffany began embracing her status as the daughter of billionaire Donald, cultivating a persona as a nepo baby influencer. Nevertheless, she reportedly felt uncomfortable with the spotlight when her dad ran for president in 2016, life as she knew it having been changed forever. "She can't really be that person ever again," biographer Michael D'Antonio told Business Insider. "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."

When Donald Trump ran for president in 2016, his youngest daughter was noticeably omitted from a documentary about the Trump family. What's more, she only had a passing mention in Fox News' "Meet the Trumps" special. This was nothing new; Tiffany Trump is the only elder Trump kid who never appeared on her dad's show, "The Apprentice." Such apparent rejection of Tiffany has led to speculation that she is the outcast of the family. Whether such claims are true or not, Donald certainly hasn't helped matters by more or less overlooking his daughter in interviews.

Interviewed by Fox News (via the Daily Mail) prior to election night in 2016, Donald was asked about his kids, and seemed to remember Tiffany at the last minute. Even then, his words were hardly those that every kid wants to hear. "I'm very proud, because Don and Eric and Ivanka and — you know, to a lesser extent 'cause she just got out of school, out of college — but, uh, Tiffany, who has also been so terrific. They work so hard," he said.

According to Michael Cohen's daughter Samantha Cohen, Tiffany never really seemed like she was part of her dad's inner circle. "This isn't anything she's explicitly said to me, but it can't be easy being made to feel your entire life like you're unwanted," Cohen told Vanity Fair in 2020, "I won't speak to her now, but if I could, I would say something."

Though her father was absent for much of her life, Tiffany Trump has had nothing but praise for Donald Trump. In 2015, she and her siblings sat down for an interview with ABC's Barbara Walters (via the New York Post), where Tiffany quelled any suspicions that she resented her status as a Trump offspring. "I'm so happy to be Tiffany Trump, happy to be in the family I'm in," she enthused.

The following year, Tiffany made one of her only appearances on her father's campaign trail, giving a speech at the Republican National Convention, per Variety. She compared herself favorably to her dad, noting that she never backs down from a challenge. "He draws out the talent and drive in people so that they can achieve their full potential," she said. "That's a great quality to have in a father. And better yet, in the President of the United States." 

What's more, she attempted to paint a far more saccharine portrait of Donald, a man renowned for his bullying tactics and invective, arguing that there's a wholesome side to him that only his children see. "In person, my father is so friendly, so considerate, so funny and so real," she added.

If the once distant relationship between Donald Trump and Tiffany Trump turned a corner when the former ran for president, it apparently didn't last. By 2018, there were claims that the pair had grown more estranged than ever after Donald entered the White House the previous year. In fact, father and daughter were said to have fallen out of touch. "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 divulged to People. "The last time she was at a family function with him, it was awkward for her and she didn't feel totally welcome."

Though Donald and Tiffany reportedly grew closer during the initial campaign trail, it appeared the two had once again reached the level of estrangement that was said to have blighted Tiffany's adolescence. Interestingly, the source alleged that becoming president had driven a wedge between Donald and his youngest daughter, though no explanation was offered as to why that was the case. "They always had a strained relationship her whole life, and it got exacerbated by the presidency," they said. "It's gotten much worse now."

Mere months into his presidency, Donald Trump banned transgender people from serving in the military. Despite this, Tiffany Trump hailed her father as an LGBTQ ally. Speaking at a Trump Pride event in 2020, Tiffany claimed that her dad had always been supportive of LGBTQ people. "Prior to politics, he supported gays, lesbians, the LGBQIA+ community," she said, per NBC News. "My father has always supported all of you. ... He's never done it for politics." Notably, she omitted the "t" from LGBTQ, though it's unknown whether this was by design or she simply misspoke.

Tiffany was widely lambasted for her remarks, with critics pointing out her father's sorry record on LGBTQ rights. Black Eyed Peas frontman will.i.am called out Tiffany on X, writing, "@TiffanyATrump, I see that you walked out to #iGOTTAFEELING...but given the inequalities in America affecting LGBTQ, people of color and the disenfranchised, this song would have been more appropriate to walk out to." He then linked to his song "Where Is the Love?," which had been modified to reflect the division of a post-Trump America.

Vanity Fair argued that the disastrous speech was a turning point in public perceptions of Tiffany, proving that she is more similar to Donald than people give her credit for.

Donald Trump's former personal secretary, Madeleine Westerhout, was fired after making some rather hurtful claims about the then president's relationship with his youngest daughter. According to a report by Politico, an intoxicated Westerhout got a little too candid while chatting to reporters at Donald's golf club in Bedminster, New Jersey, in 2019. During the conversation, she claimed that she's closer to Donald than his own daughters. She alleged that Donald was embarrassed to be seen with Tiffany Trump because he thought she was overweight, and also claimed that he wouldn't be able to pick his youngest daughter out of a crowd. "She had a couple drinks and in an uncharacteristically unguarded moment, she opened up to the reporters," said a source.

When approached by reporters following the incident, Donald was quick to defend his relationship with Tiffany. "She's going to be calling me when we get to Camp David," he said, per the New York Post. "I love Tiffany. She's a wonderful person and she studies hard."

But according to Michael Cohen's book "Disloyal," there may have been more than a hint of truth to Westerhout's claims. Cohen alleged that Donald and Ivanka Trump mocked Tiffany over her looks, while Ivanka, Eric Trump, and Donald Trump Jr. conspired against her, dubbing her the "red-haired stepchild."

Despite their alleged distance in the past, Donald Trump was a proud papa at Tiffany Trump's stunning wedding. In 2022, Tiffany tied the knot with her long-term boyfriend Michael Boulos at her father's Mar-a-Lago resort. Donald appeared to be in a great mood on the big day, seen dancing with his daughter and giving a toast to the happy couple. "Michael you better take care of her," Donald said, per Page Six. "No doubt, you are a special person and you are way beyond your years. I have seen him dealing with very big people. . . You are just two spectacular people and this was a beautiful day."

The following year, insiders told Page Six that Tiffany's wedding had been a turning point in the father and daughter's relationship. This was partly due to the large amount of donations Donald apparently received as a result of the wedding, which doubled as a political campaigning event for the Republican candidate. "The wedding was a bonding moment and she has been more accepted by the family. It brought them closer," a source revealed.

Once one of Donald Trump's closest allies, Ivanka Trump made it clear in 2022 that she would not be part of her father's 2024 presidential campaign. Accordingly, there were claims that Tiffany Trump may be in line to replace Ivanka as first daughter.

In 2023, sources told Page Six that Tiffany was slowly growing closer to her father and half-siblings, and thus becoming a more overt presence on the campaign trail. Noting the void left by her big sister's absence, Tiffany's support for Donald was, a source suggested, a strategic move for the forgotten daughter to finally have a steady father figure in her life. "If you look at Tiffany's history, she has never really been involved in the political stuff," an insider said. "Tiffany is trying to be the supportive daughter. This could be her way to get closer to her father."

That year, the two certainly appeared to be on friendlier terms. Following Donald's indictment in 2023, he reportedly held a party at Mar-a-Lago, where he danced the night away with Tiffany and her husband, Michael Boulos. According to the AP, some supporters apparently view Tiffany's marriage as a boon for Donald's campaign. Boulos, the son of a billionaire businessman, is of Lebanese descent, and his own father believes the Trump family's ties to the Boulos family could remedy the former president's fraught relationship with the Arab world. 

Following the assassination attempt on Donald Trump in July 2024, his family rallied behind him. In an emotional X post, Tiffany Trump expressed her heartache over the near-fatal attack against her father. "The outpouring of love and support for my dad is deeply appreciated," she wrote. "Thank you God for keeping my father alive." Sporting matching white ensembles, Tiffany and Ivanka Trump later appeared at the Republican National Convention to support their dad. 

There were a lot of moments from the RNC that got tongues wagging, including one particularly curious interaction between Donald and Tiffany. At one point, Tiffany was seen leaning in to kiss her father. He, in turn, swiftly moved his face away while barely acknowledging his youngest daughter. Some suggested that the kiss-dodge was evidence that Tiffany would never replace Donald's beloved eldest daughter, Ivanka. Notably, Donald did manage to offer a kiss to his granddaughter Kai Trump, who is the daughter of Donald Trump Jr. Others noted that Donald even managed to blow a kiss to wrestler-turned-MAGA mouthpiece Hulk Hogan, who gave a speech at the convention. Whether Donald, whose ear was bandaged following the assassination attempt, was simply distracted or deliberately kissed everyone but Tiffany remains up for debate.