Tiffany Trump's Biggest Controversies Over The Years

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Donald Trump's youngest daughter hardly ever makes the news for the right reasons. Over the years, millions have cringed after witnessing Tiffany Trump's many awkward moments. Worse still, several of these instances have stemmed from Tiffany's distant relationship with her famous father. When the model's birthday rolled around in 2019, Donald completely ignored her on social media and instead wished the U.S. Navy a happy birthday. In a 2016 interview with "Fox & Friends," Donald also openly admitted that he was proud of Tiffany "to a lesser extent" compared to her older half-siblings as she had only wrapped up college a few months prior (via People). 

According to a 2019 Politico report, Donald's assistant, Madeleine Westerhout, was fired after she informed reporters that he didn't like to snap photos with his youngest daughter because he perceived her as "overweight." A People insider also divulged that Donald and Tiffany's bond decayed even further during his first term. "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 confidant of Tiffany's claimed. "The last time she was at a family function with him, it was awkward for her and she didn't feel totally welcome." 

Trump snubs his daughter Tiffany as she goes in for a kiss. pic.twitter.com/17icXYhufm

— The Recount (@therecount) July 19, 2024

Plus, Donald proved Tiffany is a complete afterthought for him at the 2024 Republican National Convention by ignoring her when she offered him a kiss. These embarrassing moments make Tiffany's decision to stay under the radar as much as possible seem like a no-brainer. And unfortunately, on the rare occasions that Tiffany does make a public appearance to support her famous family, she garners controversy and backlash.

In October 2020, Tiffany Trump awkwardly shuffled onto the stage during a Trump Pride rally in Florida as "I Gotta Feeling" by The Black Eyed Peas played. Within the first few sentences of her rambling speech, Tiffany proclaimed that Donald Trump had long been a supporter of the "LGBQIA+ community," conveniently leaving out the T, which represents transgender people (via YouTube). During her chaotic 10-minute address, Tiffany ensured that the small audience knew that she and her mother, Marla Maples, had gay friends. In addition to asserting that her famous father doesn't discriminate against people for any reason, she reassured his queer followers that no amount of money could convince him not to support their community. In case it wasn't obvious enough, Tiffany wrote her own speech for the event and naturally, it wasn't well-received.

First and foremost, by that stage, the Republican president had already enacted numerous anti-LGBTQIA+ policies. In fact, in May 2019, the Washington Blade reported that the divisive politician had opposed the passing of the Equality Act, which protected the queer community from discrimination. Additionally, a GLAAD accountability tracker clearly documented how Donald had attacked the LGBTQIA+ community through his words and his administration's policies in hundreds of different ways. Many took to social media to point out these important details while Nadine Smith, the Executive Director of Equality Florida Action Inc., had an apt response to Tiffany's speech. "Donald Trump is the worst President the LGBTQ community has ever seen," she professed. "This event is a pathetic attempt to hide his appalling record and it's fooling no-one."

Tiffany Trump's former party girl lifestyle made a return at the worst possible time. While the world was dealing with the financial, emotional, and physical impact of the COVID-19 pandemic, in 2020, Tiffany was apparently having the time of her life at her 27th birthday celebrations in Miami. A viral social media video compiled clips of a maskless Tiffany celebrating with bottles of champagne and expensive food in a club, contrasting it with examples of the average person's struggles during the pandemic. After watching the video, many commentators on X, formerly known as Twitter, slammed her for being out of touch.

📺 NEW VIDEO

Retweet and watch until the very end.#ByeTiffany pic.twitter.com/xhvYNN5yWZ

— MeidasTouch (@MeidasTouch) October 15, 2020

One critic simply couldn't fathom why a 27-year-old couldn't just forgo her birthday celebrations for a year, labeling her: "Spoiled, entitled and egocentric." Later, a People insider confirmed that Donald Trump's youngest daughter did indeed have a blast with her friends while the pandemic was claiming the lives of hundreds of thousands of people worldwide. "She definitely had fun," they shared. "All week, [Tiffany and her friends] were partying, drinking and enjoying their meals." 

The Georgetown grad's friends even surprised her with a 3-tier cake with photos of her. Tiffany Trump's insanely lavish life naturally led people to think back to her Republican National Convention speech from 2020. In it, Tiffany ignored the fact that she came from a wealthy family and tried to come across as relatable by unconvincingly proclaiming, "As a recent graduate, I can relate to so many of you who might be looking for a job," (via X). 

Evidently, Tiffany Trump had greater priorities when the rest of America was dealing with the January 6 riots in 2021. She took to both X and Instagram to celebrate her half-brother Eric Trump's birthday, writing, "Happy Birthday @erictrump I love you and I'm so grateful to always have you by my side!" with a red heart emoji. The bizarre timing understandably led many X commentators to urge Tiffany to read the room. Meanwhile, one commenter also reminded her that she didn't need to make a public post amidst the chaos and could have easily reached out to her half-sibling privately instead. In response, another user quipped that Tiffany may not have the private contact information of her half-siblings. 

While one critic felt that Tiffany's birthday wishes had the same vibe that Marie Antoinette did when she proclaimed "Let them eat cake!" another pointed out that the French queen at least seemed aware of the dire circumstances. The model also notably displayed a similar inability to read the room back in 2017. While Puerto Rico was dealing with the devastating effects of Hurricane Maria, Tiffany returned from a month-long social media break. 

However, instead of using her influence to encourage people to help those affected, she posted a photo of herself wearing a black dress and stilettos. Social media commentators obviously couldn't help but call out her ignorance, with one critic writing, "Spoiled rich girl posts glam shot amid crisis to gain likes from ignorant fans of her father! Sad." Even a supposed supporter helpfully reminded Tiffany that the first daughter should ideally be compassionate amidst a humanitarian crisis.

In Pulitzer Prize winner and Washington Post reporter Carol Leonnig's 2021 book "Zero Fail: The Rise and Fall of the Secret Service," she posited that Tiffany Trump and Donald Trump Jr.'s now ex-wife, Vanessa Trump, had inappropriate relationships with Secret Service agents. According to Leonning, Tiffany started to log an eyebrow-raising amount of alone time with a certain federal employee following her breakup from Ross Mechanic. Their close relationship eventually caught the eye of higher-ups at the agency who "became concerned at how close Tiffany appeared to be getting to the tall, dark and handsome agent." However, when questioned, Donald Trump's youngest daughter and the man in question insisted that nothing inappropriate was going on, supposedly arguing that it was typical for a Secret Service agent to be with their charge when they were alone. 

However, their words apparently weren't convincing enough, and the agent ultimately reassigned from his position. According to Leonnig, it's unclear whether Donald was aware of the whispers about his daughter's inappropriate relationship at the time. Regardless, Tiffany's rep dispelled the shocking claims to the Washington Post, reasoning, "This is nothing more than gossip and is simply not true. Tiffany's experience with the Secret Service was entirely professional." In contrast, a spokesperson for the Secret Service neither confirmed nor denied them to People, stating only, "The U.S. Secret Service is aware of an upcoming book which re-hashes past challenges the agency overcame and evolved from." 

Shockingly, Tiffany Trump almost upstaged her famous father's White House exit in 2021. On January 19, the day before Joe Biden took over, she took to Instagram to announce her engagement to businessman Michael Boulos. What was intended to be a happy moment ended up being controversial due to the odd timing. Some may argue that she intentionally picked the date to carve out a place for herself in the Trump-dominant news cycle. There's also a chance that Tiffany may have grown tired of being sidelined throughout her life and decided to hurt Donald Trump's considerable ego by taking a tiny bit of attention away from the former "Apprentice" host on his special day. Or, she could have been trying to provide a much-needed distraction from Donald's supposed involvement in the Capitol riots. However, some commentators on X had other explanations for Tiffany's decision. 

One user quipped, "Lmao at Tiffany getting engaged with just enough time to make sure she gets to have her engagement photo shoot at the White House while she still has access." Meanwhile, another commentator likened the Trump family's time in office to a sitcom and joked that a "minor character" like Tiffany was simply getting the appropriate ending to her storyline. Regardless of her intentions, the announcement still wasn't enough to warrant a congratulatory post from her father. Granted, the president was probably tending to far more important matters at the time, but still, Tiffany's attempt at grabbing his attention clearly failed. Plus, one thing about Tiffany's husband might have had Donald fuming too.