The Shady Side Of Tiffany Trump

“Trump” is a scarlet letter of a name, one that irrevocably alters how someone lives and is perceived, and that’s true for even inconspicuous family members like Tiffany Trump. The only child from Donald Trump’s relationship with Marla Maples, Tiffany may have lived most of her life outside her father’s sphere of influence, but her name is a heavy mass that gravity inevitably pulls into Donald’s orbit.

Tiffany is rarely subject to the constant scrutiny paid to the Trump family, having grown up in California far from Donald’s New York City dealings. If anything, the 31-year-old is mostly mentioned in mocking ways that emphasize her as somewhat of an afterthought in the Trump family. Donald Trump reminded everyone of this during a call-in to “Fox & Friends” on November 8, 2016. “I’m very proud of my children,” said Trump. “I’m very proud, because Don and Eric and Ivanka and — you know, to a lesser extent because she just got out of school, out of college — but, uh, Tiffany, who has also been so terrific.” (per Mashable).

Ultimately, despite never working for her father in any capacity (unlike the rest of her adult siblings), Tiffany has still been caught under the shade cast by the Trump name. While she’s hardly as shady as her last name may imply, the media has nonetheless dug up some dirt on Donald’s second-youngest child over the years.

Tiffany Trump seems to have an awkward relationship with her father. As Donald Trump said in a 2004 New York Magazine profile. “You know I have another daughter, with Marla, named Tiffany? She’s just a beautiful great kid also. But it’s very separate. When you have separate wives, it’s sort of … separate.” That glaringly “separate” relationship sometimes plays out over social media, with Tiffany sometimes subtly or cryptically throwing shade at her father.

Case in point, after Donald Trump forgave former assistant Madeleine Westerhout for claiming that the president avoids photographs with Tiffany because of her weight, his daughter took to Instagram. There, she posted a saying attributed to the Persian poet Rumi, writing, “Study me as much as you like, you will never know me. For I differ a hundred ways from what you see me to be.” (via Business Insider).

Tiffany has also used social media to like and promote political messaging that’s ideologically disparate from her father’s. On March 25, 2018, Tiffany liked multiple photographs on Instagram from the March for Our Lives protest for gun control legislation (per Nylon). On June 2, 2020, Tiffany posted a black square on Blackout Tuesday in solidarity with the Black Lives Matter protests, captioning it with “#justiceforgeorgefloyd” (per Forbes). The same day on X, her father wrote of the protests, “NYC, CALL UP THE NATIONAL GUARD. The lowlifes and losers are ripping you apart. Act fast!”

While not nearly as controversial as Donald Trump’s internet activity, Tiffany Trump’s social media behavior has still come under fire from time to time (even when she’s not quietly shading her father). Known as one of the “Rich Kids of Instagram” alongside other children of famous men and women, Tiffany sometimes puts her proverbial foot in it on the social media platform.

For instance, there was the time when Tiffany commemorated 9/11 with a tactless Instagram post that had clipart of fiery explosions on an image of the Twin Towers. Then there was the cringe-inducing August 17, 2015, video Tiffany posted to Instagram of a photoshoot for fellow “Rich Kid of Instagram” Andrew Warren’s fashion line, Just Drew. The video showcased Trump and other children of nepotistic privilege dancing with remarkable awkwardness. The comment section is filled with second-hand embarrassment. “The funniest and most uncomfortable thing I ever saw on Instagram,” read one comment, with another stating, “No rhythm.”

Sometimes it’s just a matter of oblivious timing, with Tiffany posting to Instagram at precisely the wrong moment. She was lambasted for posting to Instagram on Jan. 6, 2021, while the Capitol Hill insurrection was happening, to share a smiling photo of herself and brother Eric Trump, wishing him a happy birthday. Similarly, Tiffany was raked over the coals for posting a selfie on September 30, 2017, in the wake of Hurricane Maria’s devastation (per Yahoo), which killed more than 3,000 people.

According to the 2021 book “Zero Fail: The Rise and Fall of the Secret Service,” Tiffany Trump may have had a clandestine relationship with a Secret Service agent (via The Guardian). The book, written by Pulitzer Prize-winning Washington Post author Carol Leonnig, chronicles the history of the agency and their relationship to the First Family, which isn’t supposed to get personal.

The book details how Tiffany and Vanessa Kay Trump, Donald Trump Jr.’s wife at the time, became “inappropriately — and perhaps dangerously — close” to different Secret Service agents. Leonnig writes that Tiffany, after suffering an emotionally taxing break-up, “began spending an unusual amount of time alone with a Secret Service agent on her detail.” According to Leonnig, leaders at the agency “became concerned at how close Tiffany appeared to be getting to the tall, dark, and handsome agent,” and the agent was reassigned away from Tiffany.

Tiffany and the agent in question denied that anything inappropriate occurred. Vanessa Trump was much more conspicuous, outright dating a Secret Service agent (who was not assigned to her) and ultimately filing for divorce from Donald Trump, Jr. on March 15, 2018. Tiffany would go on to date and marry Michael Boulos after meeting him in the summer of 2018. They had their first child on May 15, 2025.

The coronavirus fundamentally altered society, and the government’s reaction to it did the same. Everybody remembers lockdowns, face masks, and essential workers, and any politicians who violated their own rules were lampooned for their hypocrisy. That tangentially included Tiffany Trump, who wouldn’t let the coronavirus ruin her 27th birthday.

An unmasked Tiffany was seen partying with a group of unmasked friends in Miami on October 17, 2020, at a time when the state of Florida was seeing roughly 3,000 new cases a day, according to People. This was also barely two weeks after her own father (and staff members) contracted the coronavirus. None of that would become an impasse for Tiffany Trump’s lavish lifestyle.

Tiffany’s birthday bash lasted multiple days, with Trump and her future husband, Michael Boulos, joined by multiple people at restaurants, out shopping, and on the beach. Images were posted of her receiving a multi-tier cake with an actual image of herself on it. The hashtag “Bye Tiffany” began trending on social media, and a video that Meidas Touch posted on X subsequently went viral, editing footage and images of Tiffany partying in between videos of everyday Americans suffering from the coronavirus. It was perhaps the most vocal the Internet has ever been about Tiffany Trump, whose existence sometimes feels like her forename — empty air (Tiffany was named after the air rights above Tiffany & Company, which Donald Trump bought to build a taller tower).

While arguably the least visible child of Donald Trump (aside from his youngest child, Barron), Tiffany Trump nonetheless participated in the campaigns to elect her father, albeit sparsely. In the final few weeks leading up to the 2020 election, Tiffany hosted a handful of events which you wouldn’t associate with the Trump name, including a “Trump Pride” event on October 17, 2020.

Tiffany’s 10-minute speech at the Tampa event was widely ridiculed for a variety of reasons. Tiffany has a suspicious and likely intentional habit of omitting the acronym letter for “Transgender” when spelling out LGBTQ+, instead saying, “LGBQIA,” something she has repeated textually on social media and elsewhere, as noted on X. Excluding transgender people from something as seemingly inviting as a pride event drew obvious criticism.

Perhaps Tiffany left it out for a reason, considering Donald Trump’s frequent rhetorical and legal attacks against the transgender community. “I know what my father believes in,” Tiffany said (via Mashable). “Prior to politics, he supported gays, lesbians, the L-G-B-Q-I-A-plus community, okay?” Many Trump critics subsequently pointed out Donald Trump’s anti-LGBTQ+ behavior, documented by Transequality. Her speech oscillated between bubbly enthusiasm and dark solemnity with awkward speed, moving from claiming her “best friends are gay” to mourning a friend of her mother’s who died of AIDS. Vanity Fair ended up calling the speech a “train wreck,” and Tiffany hasn’t been able to live that shade down since.