Ivanka Trump’s Most Painful Moments

Ivanka Trump

There is no doubt that, of all the Trumps, President Donald Trump is the most nervous, but the apple does not fall far from the tree. Trump’s second oldest daughter, Ivanka Trump, has had a fair amount of controversy over the years, much of which seems to have been sparked. From the moment she was introduced to the world as a promising model in her teens, the businesswoman has met with a significant number of criticisms, thanks in large part to Ivanka’s numerous comments and shady actions.

Ivanka has always been close to her father (appearing alongside him in The Apprentice to work for the Trump Organization from 2005 to 2017 and eventually join him in the White House), who, unfortunately, has not done much for his reputation. Instead of keeping his head down and working hard, he’s repeatedly tried to insert himself into the spotlight, and it backfired, in a big way. Here are Ivanka Trump’s most painful moments.

No one asked for this Trump card

In 2009 Ivanka Trump published her first book, The Trump Letter: Playing to Win at Work and Life, a “260-page business book for young women on how to achieve success in any field, based on what Ivanka Trump has learned from his father and from her own experiences.” Unfortunately, it seems that those young women were not seeking her advice.

The tome received lukewarm reviews on sites like Goodreads, which probably had something to do with the fact that it was full of scary quotes. While some statements were simply confusing: “Success is not something that happens to you; it happens to you”, others were completely deaf.

For example, writing about sexual harassment, Trump noted that “it is never acceptable,” but added: “At the same time learn to discover when a beep or scream is really a form of harassment and when it is just a good natural joke that you can return in kind.”

She even seemed to allude to the idea of #fakenews long before her father did, writing: “Perception is more important than reality. If someone perceives that something is true, it is more important than if in fact, it is true”, she continued.

“This does not mean that you should be misleading or deceptive, but don’t go out of your way to correct a false assumption if it works in your favor.” Ivanka, just stop.

Diamonds are a girl’s best friends

When Red Book published Ivanka Trump’s Guide to Looking Like a Boss in 2012, it included a fairly standard set of wardrobe tips and trips, but one did stand out. “A timeless gem, like pearls or earrings, has lasting value,” Trump told the media. “I bought a vintage ring for $ 600 with my first paycheck; I plan to pass it on to my daughter.”

The problem is that Ivanka’s first paycheck (and most of the ones that followed) was made possible by her family’s connections. Connections that also granted her the privilege of spending a full salary on a piece of jewelry because other mundane bills, such as rent, were being met.

Ivanka Trump was about to star in a sexist reality show

Donald Trump has long been involved in beauty pageants and reality shows and, like Jezebel discovered, in 2013, he tried to merge the two in an effort to launch his daughter’s television career. According to sources who spoke to the outlet, Ivanka Trump was preparing to host Trump Town Girls, a reality competition whose premise sounds incredibly sexist.

Although the show never aired, Jezebel gained access to press materials and clips from the pilot episode, which was being produced for MI!, and deduced that its main premise was “pitting beautiful contestants at Trump’s beauty pageants against hardened real estate brokers at Trump International Realty.”

Apparently, the two-woman teams were tasked with competing to see who could earn as many commissions as possible. As the outlet noted, the videos portrayed the women as “intensely competitive and malicious with each other, aware that working for Trump International means being replaced at any time by someone sexier.”

Fortunately for Ivanka, the show lacked the star power necessary to move forward, and, very soon, all mention of its existence was erased from the Internet before seeing the light of day.

She still asks ‘dad’ for permission

President Trump’s relationship with his daughter has come under intense scrutiny over the years as it accumulates, what The Independent calls, a “haunting record of comments,” such as the time The View casually said in 2006 “He said that if Ivanka was not my daughter, maybe he would date her.” It goes without saying that there have been countless times that Trump has acted totally improperly towards his daughter.

While Ivanka Trump’s part of the relationship is rarely explored, in September 2017, he became the subject of great ridicule on Twitter when it was revealed that he still refers to POTUS as ‘dad’. It was the President himself who, while inviting Ivanka to join him on stage during a speech in North Dakota, told the crowd, “She is so good that she wanted to take the trip. She said, ‘Dad, can I go with you?? She actually said, ‘Daddy, can I go with you?’ I like that, right?”

Although Ivanka dismissed the comment, video of the proclamation soon began circulating on Twitter, as it was shared by journalist David Mack, who joked , “The responses to this tweet are why I re-downloaded Twitter.”

In addition to countless gif responses showing people being shocked or vomiting, one user slammed it shut, “So the moral of this story is that @Ivanka has nothing to do, so she wants to ride the big plane with her dad.”

Ivanka Trump does not believe Americans want job security

When Fox News asked Ivanka Trump in February 2019 to comment on Representative Alexandria Ocasio-Cortez’s New Green Deal, “guaranteeing work with family wages, adequate family and medical leave, paid vacations, and retirement security for all the people of the United States,“ the daughter of POTUS had quite the reaction.

“I don’t think most Americans in their hearts want to get something,” he began, justifying, “I have spent a lot of time traveling in this country in the last four years. People want to work for what they get. She continued: “They want the ability to get a job. They want the ability to live in a country where the potential for upward mobility exists. ” Trump went on to point out that he believes the United States is doing better than in recent years and that “it is in stark contrast to the rest of the world,” which she says has “slowed down.”

Alexandria Ocasio-Cortez quickly took to Twitter to respond, noting Trump’s inability to speak on behalf of the average American worker. She wrote, “As a person who really worked for tips and hourly wages in my life, instead of having to learn about it second hand, I can tell you that most people want to be paid enough to live. A living wage is not a gift, it is a right,” she proclaimed. “Workers are often paid much less than the value they create.”

Her public love for Karlie Kloss is painfully one-sided

Here’s something you might not know about Ivanka Trump: Her sister-in-law is none other than Karlie Kloss. Lost? We got you. It’s because the supermodel is married to Joshua Kushner, also known as Jared Kushner’s brother, also known as Ivanka Trump’s husband.

If you’re a fan of Kloss, this news will probably surprise you, as she has rarely spoken publicly about her family connection. However, if you follow POTUS’s daughter on social media, you will know that she is repeatedly excited about being related to Kloss. Yes, their relationship appears to be painfully one-sided.

In July 2018, for example, Trump spoke about Kloss’s engagement announcement on Instagram and commented, “I am blessed to have you as a sister (!!!) Karlie and look forward to the decades of happy memories that we will create together as a family!” In March 2019, she shared a video of her watching Kloss presenting the Season 17 premiere of Project Catwalk in which she shouted with excitement, “Karlie, it’s happening!”

Sadly, Kloss has never responded to any of these signs of affection, nor does she follow Trump on social media, as Quick unearthed. In fact, during an interview with British Vogue, Kloss said that being related to the President’s family has been difficult. “But I choose to focus on the values that I share with my husband, and those are the same liberal values that I grew up with and that have guided me throughout my life”, she concluded.

She joked that she has “the most difficult job in the world”

When President Trump decided not to attend the 2019 Gridiron Club Dinner, which began in 1885 and is described by the Washington Post as “an exclusive gathering of politicians and media elite,” he sent his daughter on his behalf. Traditionally, the night is kicked off by the President, who shares a few “humorous comments” before “a prominent Democrat and Republican” do the same, all leading to a series of comic sketches by top journalists.

Clearly doing her best to uphold the tradition, Ivanka Trump tried to show her sense of humor at the top of the night, but as the Washington Post reported, she bombarded in front of 700 guests. Revealing that she had been asked to attend dinner that same afternoon, she joked: “The press seems to think it is ironic that I, born of great privilege, think that people want to work for what they are given. As if she were the daughter of Donald Trump, it is not the most difficult job in the world, “she said impatiently. Cue the crickets.

She wiped her hands of a difficult border problem

In May 2018, President Trump and his administration made the headlines when they presented a new policy calling for the separation of families crossing the U.S.-Mexico border illegally. As Vox revealed, adults captured by the Border Patrol between ports of entry were to be “transferred to criminal custody” while their children would be labeled “unaccompanied minors” and “sent to the care of a completely separate government department.”

Initially, Ivanka Trump spoke out against family separation, but when Facing the Nation when asked about the issue in December 2019, she tried to wash her hands about it. “We went and looked, and Homeland Security says there are still around 900 children who remain separated from their families,” host Margaret Brennan told Trump, asking, “Is this something you continue to be engaged in?”

Instead of giving an affirmative or negative answer, Trump shifted responsibility and said, “Well, immigration is not part of my portfolio.” She continued: “Obviously, I think everyone should be involved, and the full force of the United States government is committed to this effort for border security, to protect the most vulnerable.”

Still not answering the question, she shifted gears and followed a confused tangent, talking about human trafficking and praising herfather. She added: “That includes those who are trafficked across our border, who this President has pledged to counter and combat human trafficking in an incredibly comprehensive and aggressive manner.”

Was Ivanka Trump snubbed by world leaders?

The official White House website may have Ivanka Trump listed as ‘Advisor to the President’, but her role has been the subject of many questions and a huge debate since Day 1. And it’s not just Americans who seem confused about her duties. When Ivanka Trump appeared at the G-20 summit in Osaka, Japan in July 2019, it was a large number of world leaders who publicly turned on her.

In a video, which was originally posted on the Twitter account @elysee (also known as the French Presidential Palace), Trump was shown uncomfortably trying to engage in a conversation with French President Emmanuel Macron, British Prime Minister Theresa May, the Canadian Prime Minister Justin Trudeau and IMF Managing Director Christine Lagarde, and be repeatedly rejected.

The exchange was truly embarrassing and inspired the #UnwantedIvanka meme, which saw people photograph Trump in famous scenes, such as a Bad Girls motionless movie with the caption “She’s Not Even Going Here,” or the iconic Beatles Abbey Photo Road. Meanwhile, Rep. Alexandria Ocasio-Cortez wildly tweeted, “It may be shocking to some, but being someone’s daughter is not really a professional qualification.”

While Trump did not comment on the discomfort, she definitely must have felt it. As body language expert Patti Wood summed up at Refinery29, “She stayed a little out of the circle, in a way that shows she didn’t feel welcome. Furthermore, the group did not turn to her to allow her to enter completely.”

Ivanka Trump’s work trips leave the public confused

Ivanka Trump’s appearance at the 2019 G20 summit was not the only surprising work trip the First Daughter has taken since her father became POTUS in January 2017.

In September 2019, for example, she flew to Bogotá, Colombia, where she met with the country’s president and vice president, opened the Academy of Enterprising Women, and visited a Venezuelan migrant camp. While Colombian Vice President Marta Lucía Ramírez explained to the local newspaper how long the mission of the trip was “to show her the different projects we have for the economic empowerment of women,” things did not turn out that way.

First, a slight wardrobe malfunction (in which the wind ravaged Ivanka Trump’s statement sleeves) stole the show and made the rounds on Twitter, then the media began attacking her with the New Zealand Herald doubling the ride a benign diplomacy mission and GQ asking, “What about immigration detention camps here in the United States?”

Just a few months later, in February 2024, Trump’s travels were again criticized when she joined the president on a state visit to India. While Fashion raised the question, “What exactly is Ivanka Trump doing in India?” The Huffington Post was not holding back when it proclaimed, “Americans cannot understand what Ivanka Trump is doing in India. In addition to tagging dad with the taxpayer’s dime.

Her praise of the Justice Department failed, in a big way

In October 2019, Ivanka Trump turned to Twitter to praise the Justice Department’s arrest of 330 people and the rescue of 23 children in what the Department described as a “takedown of the largest child pornography website.” After tweeting a link to the Department’s official press release, Trump shared a warning to the world, writing, “Our message to those who produce, distribute and receive child pornography is clear: You can try to hide behind the technology, but we will find it and we will. We will arrest and prosecute.”

Unfortunately, despite the praiseworthy news, as Queerty noted, things “got really awkward very quickly” when Twitterverse turned to Trump. The response was harsh, to say the least, as users pointed out the hypocrisy of his tweet, highlighting her father’s friendship with convicted sex offenders. “George Nader visited the White House 13 times,” one celebrity user, while another noted, “Your dad was a good friend of Jeffrey Epstein.”

Another critic went so far as to accuse the president of “traffick [ing] young women through his modeling agency,” while some were simply offended by Ivanka Trump’s choice of words. As one user applauded “Ivanka said ‘We’ did this. Ivanka did absolutely nothing.”