The Tragedy Of Tiffany Trump

Named after New York’s most famous jewelers, Tiffany Trump was born into a dynasty that, at the time, was strictly business, but has since entered the political stratosphere in ways that few could ever have imagined. But while half-siblings Ivanka, Eric, Donald Jr., and Barron Trump have barely been out of the press following Donald Trump’s ascent to the White House, the socialite has kept a much lower profile.

Whether that’s of her own making or not is up for debate. Whenever Tiffany has sought out the limelight, things haven’t necessarily gone her way — see the disastrous speech for Trump Pride, for example. But there’s also plenty of evidence to suggest that she’s not been afforded the same opportunities, or given the same respect, as her more outspoken relatives. From failed extortion plots to flop pop careers, that’s not the only tragic situation she’s found herself in.

Six years after Tiffany Trump was born, her parents, Marla Maples and Donald Trump, divorced. Inevitably, after moving from New York to California with her mom, the future socialite very rarely got to see her dad. In fact, she essentially grew up with a single parent.

In a 2016 interview with People, Maples explained that while Donald was always a great provider financially, his day-to-day relationship with Tiffany was practically non-existent: “He loves his kids. There’s no doubt. But everything was a bit of a negotiation.”

Maples, who took herself and Tiffany across the other side of America to avoid the limelight, also revealed that she always had to make the effort when it came to contact. At least twice a year, the actor would take her daughter to the Big Apple for some quality Donald time in his office and at dinner: “I just said it’s important for her to form her own relationship with him, without my input. I wanted to create some consistency where she could see him.”

While Donald Trump has put his fingers in many pies over the years, he’s thankfully spared us all of any musical endeavors. The same can’t be said for his youngest daughter, however, even if Tiffany Trump’s short-lived music career ended pretty much before it even got started.

Indeed, in 2011, a 17-year-old Tiffany Trump tried to gatecrash the EDM scene with a heavily autotuned electro-pop song titled “Like a Bird,” the recording of which was shown in a segment on “The Oprah Winfrey Show.” “I love music, it’s always been a big passion for me,” the socialite claimed in the clip.

“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 — to a professional level,” Tiffany continued before revealing that her education was a higher priority at that moment in time. Sadly, “Like a Bird” made little impression, and staying true to her word, the very brief pop star decided to abandon any chart-topping, Grammy-winning dreams for degrees in sociology, urban studies, and law.

Having largely grown up outside of the Donald Trump bubble, Tiffany Trump has often been dismissed as the black sheep of the two-time president’s family. And it’s not just the physical distance that’s led to such a label.

Indeed, there have been several signs that Tiffany — unlike her older half siblings — doesn’t always agree with her father’s political views, and particularly the issue of gun violence. In 2018, she Instagram liked a sign from the New York March for Our Lives protest which read (via Refinery29), “Next massacre will be the GOP in the midterm elections.”

There are the occasional upsides to being left out in the cold, however. In 2022, Letitia James, the New York Attorney General, filed a lawsuit against the POTUS and his close circle for deliberately filing over 200 false assets and property valuations in order to boost Donald’s net worth. While Eric, Ivanka, and Donald Trump Jr. were cited, Tiffany’s name was nowhere to be found.

Tiffany Trump may well have thought she’d be able to build a stronger relationship with father Donald Trump when she didn’t have to rely on her mom flying her out to New York twice a year. But sadly, her father-daughter bond has apparently weakened since she became an adult.

According to a People insider in 2018, Tiffany had actually seen Donald less since his ascent to the White House. Indeed, even when she was living much closer to her father while studying law at Georgetown University, the socialite could go months without any contact. “The last time she was at a family function with him, it was awkward for her and she didn’t feel totally welcome,” the source claimed.

It’s not known which function was being referenced, but Tiffany had recently visited the White House for Easter celebrations and Donald’s Mar-a-Lago estate for Christmas. “They always had a strained relationship her whole life, and it got exacerbated by the presidency,” the insider continued. “It’s gotten worse.”

Donald Trump is no stranger to saying the quiet part out loud. But even his biggest champions at “Fox and Friends” seemed a little taken aback at just how candid he was during an on-air phone conversation in 2016. And unfortunately for his youngest daughter, Tiffany Trump, she was the subject.

Donald had called the network for just one last bit of campaigning on the first of his three consecutive election days. He appeared to believe that talking about his kids would be a winning tactic. “I’m just looking at them right now as an example,” the Republican candidate said (via Mashable). “But I’m very proud ’cause 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’s also been so terrific. I mean, they work so hard.”

Yes, not for the first or the last time, poor Tiffany appeared to be an afterthought in Donald’s mind. Of course, this last-minute display of insensitivity didn’t do any harm, and the father-of-five went on to stage a remarkable victory over opposing candidate Hillary Clinton later that night.

Was Tiffany Trump really snubbed at New York Fashion Week in 2017? The jury still seems to be out. The drama began when ex-Wall Street Journal fashion writer Christina Binkley tweeted that no one wanted to sit next to Donald Trump’s youngest daughter – no stranger to wearing ridiculously expensive outfits herself – at the exclusive event.

Adding fuel to the fire, Elle’s Nikki Ogunnaike also took to the same platform to remark on the chaos that had apparently unfolded over seating arrangements. The senior fashion editor claimed that some of her colleagues intentionally distanced themselves from Tiffany because of the negative political associations it would bring. Philipp Plein, whose show was the center of the confusion, later criticized those who’d apparently fled, telling TMZ, “Tiffany Trump is not a politician, she’s a teenager.”

However, Binkley later came to Tiffany’s defense, arguing that far from the little girl lost routine reported in the press, the law school graduate had been too busy socializing to notice the kerfuffle. Binkley told People (via Time), “It’s easy to assume from a photograph that she sat there, humiliated, with empty seats by her, which wasn’t the case … No one was mentioning Trump or addressing the Trump family directly.”

Tiffany Trump might now be happily married to Donald Trump-supporting Lebanese-American businessman Michael Boulos. But her first public, serious relationship was with a Democrat computer science graduate named Ross Mechanic. And she went through heartbreak when, in 2018, the pair decided to call it a day.

The split occurred at the same time that Tiffany relocated from the Big Apple to study law at Georgetown University. “It was all about her moving to D.C.,” explained an insider to Page Six. “Ross didn’t want her to go there without him, as he lives in New York. He wanted to be with her 24/7, and with Tiffany away in another city, it became a huge disagreement, and they decided to go their separate ways.”

The couple first met while studying at the University of Pennsylvania, and despite their differing political backgrounds — Mechanic’s real estate attorney father Jonathan had pledged thousands of dollars to Hillary Clinton’s presidential election campaign — dated for two years. It seems fair to say that his mother wasn’t too distraught about the break-up, though. When asked about the coverage of the news, a surprised Wendy Mechanic reportedly answered to the Daily News, “I’m guessing nobody even cares.”

Donald Trump’s personal assistant Madeline Westerhout certainly didn’t hold back while talking with reporters at a dinner in 2019. In fact, she was so loose-lipped about the ongoings at the White House — and perhaps most notably her boss’ relationship with Tiffany Trump — that she was subsequently fired from her post.

Westerhout alleged that Donald was so distant from Tiffany that he would struggle to pick her out of a lineup and that she herself had a stronger connection with the president than his own flesh and blood. If that wasn’t brutal enough, the blabbermouth also claimed that Donald had a problem appearing in photos with his youngest daughter because he believed she was overweight.

Although Tiffany didn’t explicitly address the hurtful remarks, she did post a cryptic message on her Instagram Stories, which many construed as a response: “Study me as much as you like, you will never know me,” she wrote (via Business Insider), quoting poet Rumi. “For I differ a hundred ways from what you see me to be. Put yourself behind my eyes, and see me as I see myself. Because I have chosen to dwell in a place you can’t see.”

In January 2021, Harry Brant — the son of publishing mogul Peter Brant and model Stephanie Seymour — was found dead after accidentally overdosing on prescription drugs at the age of just 24. As one of his closest friends, Tiffany Trump was left understandably grief-stricken.

The law school graduate had only just been partying and celebrating with Harry weeks earlier, as evidenced by the New Year’s photo of the pair at Donald Trump’s Mar-a-Lago estate she shared in her Instagram tribute. “Words can’t express how special you were and will always be to me and to all of those who had the honor to call you their friend,” she wrote in a heartfelt post that also quoted a 13th century poem from Rumi.

Tiffany, who also regularly hung out with Hugh’s brother Peter Jr., went on to add, “You were such a positive bright light and shared that spirit with all of those around you. I will cherish our memories and friendship forever. I love you!”

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA’s National Helpline at 1-800-662-HELP (4357).

In 2024, Tiffany Trump joined half-siblings Eric and Donald Jr. at Manhattan Criminal Court to support their father during his hush money trial. The former Kappa Alpha Theta member, who also brought Lebanese-American husband Michael Boulos along, no doubt got more than she’d bargained for.

The trial, of course, centered on allegations of Donald Trump paying off adult entertainer Stormy Daniels shortly before the 2016 presidential election to stay quiet about an extra-marital affair and falsifying official records to hide this fact. But the 45th’s former lawyer, Michael Cohen, also threw some more high drama into proceedings when he claimed that Tiffany had been at the center of an extortion plot target around the same time.

Cohen said that he’d spoken with both Tiffany and The National Enquirer’s one-time published David Pecker about the crime back in 2016 and, in particular, the ways in which to shut it down. However, no further information about the scheme, or the plans to foil it, has ever been released.

Tiffany Trump suffered another major loss in 2024 when her beloved maternal grandfather, Stan Maples, died at the age of 82. Her mother, Marla Maples, confirmed the news on Instagram just days after revealing that her dad had been experiencing issues with both his heart and mind.

Stan had attended Tiffany’s wedding to Michael Boulos two years earlier, and in 2016 was seen celebrating his 75th birthday in a family snap which included the University of Pennsylvania graduate. While Donald Trump’s youngest daughter was inevitably hit hard by the news, she and her mom were helped in the grieving process by a well-timed trip to Germany.

Indeed, the pair spent several days undergoing several healing practices at the Lanserhof Regenerative Center. “This was planned on the physical level weeks before and who would’ve known the timing would’ve been so perfect,” Marla captioned an Instagram snap of the retreat. The actor is a strong advocate for alternative therapies and medicines and even tried to convert her dad before his passing.

Even the most committed Democrat couldn’t help feel sorry for Tiffany Trump when she was snubbed by her own dad in the most embarrassing of ways at the 2024 Republican National Convention. While everyone was taking their seats at the Milwaukee event in time for Hulk Hogan’s appearance, Tiffany came face to face with Donald Trump. Everything initially seemed fine as the pair appeared to exchange smiles and pleasantries. But the socialite was left humiliated when after leaning in a for a fatherly kiss, the 45th turned his head away, leaving his daughter hanging.

Whether this was accidental or not, the press soon jumped it on as a snub. To make matters worse, Donald then happily allowed granddaughter Kai to give him a kiss. Still, Tiffany can take consolation from the fact that the POTUS himself was also given a similar brush off by his own wife Melania Trump at the same convention.

Mother Nature appeared determined to put a stop to Tiffany Trump and Michael Boulos’ lavish wedding in 2022. Just days before the ceremony at Donald Trump’s Mar-a-Lago estate was due to take place, weather forecasters announced that a hurricane was soon about to wreak havoc on all the plans.

Staff at the venue were subsequently sent home, a golfing get-together also had to be postponed, while flights to and from Palm Beach International Airport were canceled, leaving the bride-to-be “flipping out” according to a Page Six insider. Although the National Hurricane Center didn’t predict that Tropical Storm Nicole would hit the wedding directly, it did anticipate some rainy and windy side effects.

Luckily, crisis was averted when the storm was downgraded to a tropical depression. And the father of the bride was even able to joke about the drama in his speech, reportedly telling guests (via Mirror), “They were worried about rain. They said, ‘Sir, we are going to build a big tent over the pool’ … And I said, ‘Let’s take our chances, right Tiff?'” In a rare sentimental display, Donald even interpreted the fortunate change in weather as a sign, adding, “I think it’s emblematic for you and your life and we are very proud of both of you. Have a great life together.”

Having married wealthy businessman Michael Boulos, Tiffany Trump might no longer need to worry as much about her possible inheritance, or lack thereof, from her two-time president father. According to a People source, one of the reasons why Tiffany and her mom, Marla Maples, had been so courteous to the POTUS over the years was the uncertainty of his financial legacy.

Donald Trump didn’t exactly quell any of Tiffany’s inheritance concerns during a 2005 appearance on “The Howard Stern Show” that was unearthed several years later. In the audio footage, Donald claimed that Ivanka and Donald Jr. tried to get their younger half-sibling booted from any will proceedings. “I have a friend who is also like a very rich guy,” the entrepreneur said (via Newsweek), perhaps trying to justify his offspring’s behavior. “And he said how his children hate the new children coming along and everything else; I said, ‘Yeah, because every time you have a child, it’s 20% less.'”