10 Rumors About Tiffany Trump We Couldn't Ignore

The picture some reports paint of Tiffany Trump is one tinged with tragedy: a sidelined daughter who holds a tenuous position in her family hierarchy. But while it may seem like she often gets overlooked, she hasn't escaped the notice of the tabloids. Just like her dad, she's seen rumors and gossip about her career, love life, and family relationships hit the headlines.

Donald Trump and Marla Maples named their daughter after Tiffany & Co., the luxury jewelry brand. Because Donald had infamously cheated on his first wife, Ivana Trump, with Maples, Tiffany's parents were tabloid regulars, and she made occasional cameos alongside them after her birth in October 1993. When she was around6 months old, the National Enquirer claimed that Donald and Maples thought a chiropractor could put a halt to Tiffany's colic-induced crying, which was keeping them up at night. "Shocked docs claim it's crazy," the tabloid wrote of little Tiffany's purported spinal treatments (via FiveThirtyEight).

Tiffany was a tween when Donald's recollection of his reaction to Maples telling him she was pregnant created an enduring tidbit of gossip. "I said, 'Well, what are we going to do about this?'" he recalled on "The Howard Stern Show" in 2004 (via Newsweek). When his remarks resurfaced after he won the presidency in 2016, Donald was forced to deny speculation that he had wanted Maples to get an abortion. And with the renewed interest in Tiffany came a wave of new rumors about the first daughter.

If some reports are to be believed, Tiffany Trump and Donald Trump never developed a close relationship. Unlike her older half-siblings — Ivanka Trump, Donald Trump Jr., and Eric Trump — Tiffany didn't spend most of her childhood in New York, which made it difficult for her to see her father often. One source told The New York Post that Tiffany had to settle for a yearly two-week-long visit to Mar-a-Lago. Beyond that, another insider told People of her relationship with Donald that she "had very little to even do with him." And according to former Trump family attorney Michael Cohen, Donald wasn't excited to hear from Tiffany outside of her annual stays at his Florida club. "She would call; he'd roll his eyes," Cohen said on his "Political Beatdown" podcast in 2024.

It's become a widely held belief on the internet that Tiffany is Donald's least-favorite child, and Marla Maples even told The New York Times that her daughter's three older siblings had a closer relationship with their dad growing up. "She'd like to get to know her father better and spend time with him like his other children did: by going to his office and watching him work," she stated.

While Ivanka, Eric, and Donald Jr. became supporting stars of his 2016 presidential campaign, Tiffany only made rare cameo appearances, which helped fuel the gossip that her father isn't all that fond of her. According to a 2018 People report, Tiffany started seeing even less of her dad after he won the election. "The last time she was at a family function with him, it was awkward for her, and she didn't feel totally welcome," a source said.

According to the National Enquirer, Tiffany Trump was just 3 years old when she got bitten by the music bug and "imperiously ordered a piano player to move over so she could sing with him at a Nantucket restaurant" (via FiveThirtyEight). Fourteen years later, she recorded an auto-tuned pop ditty titled "Like a Bird." Just eight words in, it became evident that she was not the next Taylor Swift. "Diamonds are so shimmery/Special things uncover me," she sings. Deep.

After she dropped the track in 2011, Tiffany spoke about her musical aspirations on "The Oprah Winfrey Show." "It's more of a hobby right now, but we'll see in a couple of years if I actually do want to take it to the next level," she said. But according to The New York Post, she was serious about pursuing a music career, and she had a scheming wannabe stage mom who was trying to help make her dreams come true. "Around the time she started singing, Marla arranged to have a paparazzi shoot staged," an insider said. "Tiffany kept saying how she was going to be a pop star."

Tiffany's music career never took flight, but in 2017, a Santa Monica Observer report claimed she was going to sing "I'm Like a Bird" — not her song but the similarly titled 2000 Nelly Furtado hit — at her father's inauguration. A Trump Organization rep denied this, and the reporter responsible for the story told BuzzFeed it had come from a friend with inside info about the inauguration. However, BuzzFeed pointed out that the Santa Monica Observer has a history of publishing blatantly false reports.

Donald Trump has been body-shaming women for years. In a 2013 "Showbiz Tonight" interview, he even called Kim Kardashian "a little bit large" when she was pregnant — that's right, pregnant — with North West (via The Hill). Because one of his favorite topics seems to be the way women look, it was probably fairly easy for many Politico readers to believe Donald's former personal assistant Madeleine Westerhout when she told reporters that he was so embarrassed by Tiffany Trump's weight that he avoided taking photos with her. Of course, Donald denied ever disparaging his daughter in such a manner, insisting to reporters, "I love Tiffany."

Donald has made it abundantly clear how he feels about his other daughter Ivanka Trump's appearance. "She's got the best body," he creepily boasted on "The Howard Stern Show" in 2003 (via Politico). The proud dad was chatting with Howard Stern about Ivanka Trump's modeling career. But according to Michael Cohen, Donald and his eldest daughter both agreed that, unlike Ivanka, Tiffany wasn't fashion industry material. In his book "Disloyal," Cohen recalls a conversation he, Donald, and Ivanka had about Tiffany's pursuit of an internship at Vogue. "'I don't think Tiffany has the look,' Trump said to Ivanka and me. 'She just doesn't have what you have, honey,'" Cohen writes. "'I agree, Daddy,' Ivanka said. ... 'She just doesn't have the look is the right way to say it, Daddy.'" However, according to Vanity Fair, Tiffany got the Vogue job with Ivanka's help.

After Donald Trump threw his hat in the ring for president in 2015, the media became fascinated with Tiffany Trump's association with a group known as "The Rich Kids of Instagram" or "The Snap Pack." Tiffany earned a reputation as a party girl by hanging out with the crew of wealthy socialites, who flaunted their lavish lifestyles on social media before it became oversaturated with influencers. Members included Robert F. Kennedy Jr.'s daughter Kyra Kennedy and post-Impressionist painter Henri Matisse's great-great-granddaughter Gaia Matisse. 

In 2015, the Daily Mail reported that Tiffany and two other Rich Kids, Reya Benitez and Andrew Warren, had gotten so out of control during a Jason Derulo concert that security warned them to calm down. And after Donald's victory, one friend told Us Weekly that Tiffany and the Rich Kids were "going to make the White House their new locale. They're ready to up their Instagram game big time."

Allowing a bunch of Instagram influencers to take over the White House might have seemed like a laughable concept then, but during his second term, Donald started treating some conservative influencers like legit members of the press, including Barron Trump's friend Bo Loudon and conspiracy theorist Jack Posobiec. However, no Snap Pack takeover ever took place, and some sources have called into question Tiffany's Rich Kid cred and party girl rep. "Some of her friends are pretty obnoxious and entitled. They have Birkins and souped-up Range Rovers, but she's pretty down-to-earth," one insider told The New York Post. Another source told Us Weekly Tiffany is so financially responsible that she won't even run up her room service bill when she's staying at one of her dad's hotels.

Tiffany Trump's Vogue internship didn't lead to a career in fashion, which might be a good thing; having some bad experiences with those in the industry could have been her villain origin story, à la Cruella de Vil. Tiffany's photographer pal Scott Nathan told The New York Post that designer Michael Schmidt wouldn't help Tiffany when she needed an outfit for the Republican National Convention in 2016 because she was "radioactive." When Tiffany attended New York Fashion Week months later, some reports claimed that she still wasn't being warmly welcomed into the fashion fold.

Fashionista reported that some fashion editors asked to be seated elsewhere at the Philipp Plein show because Tiffany had scored a front-row seat and they presumably didn't want to be anywhere near her. Vogue Business Editor-at-Large Christina Binkley also shared a photo of the empty seats next to Tiffany on X and wrote, "Nobody wants to sit next to Tiffany Trump at Philipp Plein, so they moved and the seats by her are empty."

It appeared that attendees were going all "Mean Girls" on Tiffany, but by refusing to sit beside her instead of telling her, "You can't sit with us." The seeming snub earned Tiffany some sympathy from Whoopi Goldberg, but her Snap Pack pal Andrew Warren insisted that she had actually been given a place of honor at the runway show. "That seat was never empty it was reserved for [Plein's] family," he captioned an Instagram post. In another update on the seating drama, Binkley was forced to admit that Warren was right. "The two seats remained empty for about 2 minutes before others sat there," she wrote. "Then Philipp Plein's sister made them move so she could sit there."

Some reports suggest that Tiffany Trump had a ridiculously privileged childhood, with the National Enquirer (via FiveThirtyEight) claiming that she once got "a doggie bag" for her caviar while dining out at age 3. She was also a toddler when she attended a party in a ratty, threadbare skirt. One adult attendee was informed that it was no poor Cinderella situation, telling The New York Times, "[S]omeone told me it had belonged to Shirley Temple."

As Tiffany got older, reports about her financial situation suggested that she was no longer living large. Recalling what Tiffany confessed to him when he encouraged her to ask Ivanka Trump if she could borrow an outfit for the Republican National Convention, Scott Nathan told The New York Post, "She said 'I don't want her to know I don't have any money.'" A source also told Vanity Fair that Donald Trump only gave Tiffany a monthly allowance of $500 when she was in college. People further reported that Donald had little interest in her financial future. Of her inheritance, a source told the magazine, "[S]he says she is not guaranteed anything."

The insider claimed Tiffany's support for her father is directly tied to her concerns about her inheritance, and some netizens also believe this to be the case. When Michael Cohen's daughter, Samantha Cohen, spoke to Vanity Fair in 2020 about her former friend, she wasn't convinced that Tiffany was a MAGA true believer. "When I see her speaking at the RNC, I know there's no way she believes that s***," she said.

In her 2021 book "Zero Fail: The Rise and Fall of the Secret Service," journalist Carol Leonnig claims that Tiffany Trump "began spending an unusual amount of time alone with a Secret Service agent on her detail" after a breakup (via The Guardian). Their closeness was reportedly concerning enough that the agent was removed from her security team. However, a Trump rep told The Washington Post the insinuation that the first daughter was living out a bad romance novel plot was merely "gossip," insisting, "Tiffany's experience with the Secret Service was entirely professional."

The breakup Leonnig refers to in her book could be that of Trump and her longtime boyfriend Ross Mechanic. According to Page Six, they didn't end things on the best of terms in 2017 when they disagreed over turning their relationship into a long-distance arrangement. "It was all about her moving to D.C.," an insider explained. "Ross didn't want her to go there without him, as he lives in New York. He wanted to be with her 24/7."

Perhaps Trump didn't really seek solace in the arms of a Secret Service agent after her split, but in 2017, the Daily Mail published photos of Tiffany laughing and holding hands with a member of her security detail, who even flashed a smile at the photogs. It was an unusually affectionate way for the first daughter and someone who had been hired to protect her to interact ("entirely professional," indeed).

Ivanka Trump began distancing herself from her father after he left the White House in January 2021, even announcing that her political career was over in 2022. A People source claimed Tiffany Trump shared her older sister's lack of interest in playing a role in Donald Trump's 2024 presidential bid, telling the outlet in August 2023, "They want nothing to do with politics this time around." But was Tiffany really plotting to step in and become the favored first daughter with Ivanka out of the picture?

Speaking to Page Six in April 2023, a source had suggested that Tiffany's presence at the speech Donald gave after his arrest in Manhattan spoke volumes because it was a rare instance when she was there for her father while Ivanka was not. "Tiffany is trying to be the supportive daughter," they stated. Then, in June 2023, OK! USA reported that Tiffany saw Ivanka's decision to exit politics as her chance to become the star of the show, much to Ivanka's consternation. "[Ivanka] didn't think Tiffany had it in her to emerge from the shadows and grab the spotlight in their father's life," said an insider. "She tells Donald that Tiffany doesn't have the savvy and guile to be a trusted advisor to him." But according to the source, Ivanka's father likely ignored her warning because she had left his inner circle.

The People source had a different take on the two sisters' relationship, saying, "They used to not get along but now they're bonded over their shared trauma of being the most hated kids in America."

Tiffany Trump married Michael Boulos at what just had to be her dream venue: Mar-a-Lago. Donald Trump once boasted on Truth Social that his beach club is the "Center of the Universe," but it came dangerously close to winding up in the center of a hurricane during Tiffany's wedding festivities in 2022. And unfortunately for the first daughter, her daddy couldn't swoop in and save the day by changing the looming storm's trajectory with a few deft strokes of his trusty Sharpie. "Tiffany is flipping out," a source told Page Six. The insider added that some wedding events had been called off due to the weather.

Reports built the event up as an extravagant, massive celebration with a lengthy guest list. "They both want to marry in a big ceremony, your basic international spectacle," said a People source. However, a rep for Tiffany told Page Six, "Tiffany and Michael's wedding is an intimate wedding with family and very close friends."

The rep further insisted that the bride wasn't going all Tropical Storm Tiffany by "flipping out" over the weather, which turned out to be fine on her big day. "Tiffany is very calm and [has] never been worried about the weather," they stated. But according to Page Six, Donald claimed otherwise in his wedding speech when he said of the newlyweds, "They were worried about rain." He also admitted that he ignored the couple's plea to cover the pool with a tent because "it costs a lot of money." But apparently, there was a downpour of cash at the event. As an insider told Page Six, "The wedding was a huge political event and had a lot of donors." How romantic.

Donald Trump is all about excess, as evidenced by how he's brought his gilded Mar-a-Lago gaudiness to the White House. And the Mar-a-Lago face trend is all about excessive cosmetic work. But when Tiffany Trump shared a tuned-up selfie in 2025, it wasn't like making some minor renovations to the White House; it was like Donald demolishing the entire East Wing and replacing it with a ballroom.

In the comments section of Tiffany's Instagram post, observations abounded that she didn't look like her old self. Some Instagrammers also suggested that she was going overboard with the lip filler, and there's been speculation online that she got a nose job at some point. Dr. Gary Motykie told Radar he agrees that these are two procedures Tiffany has likely used to alter her appearance. The plastic surgeon also estimated that she's spent around $100,000 on her MAGA makeover. 

Another plastic surgeon, Dr. Dennis Schimpf, told The List that Tiffany's other possible cosmetic enhancements include Botox injections and chin and cheek filler. Of why the first daughter might find fillers such an attractive option, the doctor explained, "No recovery time is involved. The volume can be slowly increased over time by slowly adding filler every few months as needed or desired." So, it's not exactly like unleashing a wrecking crew on a piece of American history.