The Most Cringeworthy Trump Family Moments

Critics frequently state that the Trump family is often in the news for all the wrong reasons. Donald Trump's controversial presidency caused the world to focus its attention on the chaotic family even more than ever before. Of course, this resulted in seemingly endless headlines and news segments documenting the then-first family's often "not-so-presidential" behaviors. Many of their controversial moments have resulted in full-blown scandals and escalated into lawsuits. Still, the Trump clan sticks together.

Ivanka Trump, Eric Trump, Tiffany Trump, and Donald Trump Jr. — all Donald Trump's offspring — often defend the family's antics and especially their father's polarizing opinions. When Trump announced in 2015 that he was planning to run for President of the United States, he ruffled many a feather. His kids didn't seem to care though, sharing a statement with People that read in part, "Our father, Donald J. Trump, is a true visionary and a great mentor. He is a brilliant negotiator with a proven track record of getting things done. Most importantly, he is an incredible dad and role model. He raised us to work hard and strive for excellence in all that we do." Do you think the Trump kids regretted this statement down the road? Perhaps not, because the entire family has dabbled in controversy at one point or another. With that in mind, let's reminisce on the most cringeworthy Trump family moments.

Melania Trump's jacket caused quite a stir

Melania Trump's infamous "I really don't care" jacket caused a great deal of controversy back in 2018. To recap, the former first lady was photographed in the bold fashion choice while traveling to and from McAllen, Texas to visit Upbring New Hope Children's Shelter, which houses migrant children. In the photos, Melania can be seen in a green jacket with the words "I really don't care, do u?" written across the back. This raised many questions. Some wondered if Melania was trying to send a message about how she felt about her husband's immigration policies.

The then-first lady's spokesperson, Stephanie Grisham, argued that this wasn't the case. Grisham took to Twitter to share: "Today's visit w the children in Texas impacted @flotus greatly. If media would spend their time & energy on her actions & efforts to help kids – rather than speculate & focus on her wardrobe – we could get so much accomplished on behalf of children. #SheCares #ItsJustAJacket." However, Melania gave a different explanation for her decision to wear the jacket in an interview for ABC News. "It was for the people and for the left-wing media who are criticizing me. And I want to show them that I don't care," she explained. This statement aligned with a tweet from Donald Trump that offered a similar explanation for Melania's cryptic fashion choice.

The family didn't attend Joe Biden's inauguration

The Trump family made history when they chose to skip U.S. President Joe Biden's Inauguration. According to CBS News, Donald Trump was the only president in recent years to opt out of their successor's inauguration. You might recall Trump's claims of election fraud following the 2020 U.S. election. The former U.S. president seemed to be resistant to Joe Biden taking over his role in the White House, so perhaps this is why he didn't attend his inauguration. "This is a fraud on the American public," Trump said during a speech following the 2020 election (via C-SPAN). He continued, "This is an embarrassment to our country. We were getting ready to win this election. Frankly, we did win this election. Our goal now is to ensure the integrity for the good of this nation."

Then President-elect Joe Biden reacted to Trump's announcement regarding not attending his inauguration during a conference (via NowThis News) in January 2021. He stated, "I was told that ... he indicated that he wasn't gonna show up at the inauguration," Biden said of Trump. "One of the few things he and I have ever agreed on. It's a good thing, him not showing up." He went on to confirm that he had changed his mind regarding Trump's attendance. He previously wanted the former president to show up to set a positive example, but it seems that Trump's handling of the attack on the U.S. Capitol put an end to this.

Donald Trump made shocking comments about Ivanka Trump

Donald Trump's relationship with his daughter, Ivanka, has been labeled by some as bizarre. This is because Donald has a long history of making inappropriate comments about Ivanka. During an appearance on the Howard Stern show in 2004 (via CNN), the former U.S. president gave Stern permission to call his daughter "A piece of a**." 

Trump's comments, which many would consider disturbing, are nothing new. You might recall that the businessman made an arguably even more unsettling statement about Ivanka during a 2006 appearance on "The View." Things took a turn for the worse after Trump was asked whether or not he would approve of his daughter gracing the cover of Playboy magazine. "I don't think Ivanka would do that inside the magazine, although she does have a very nice figure." the former president said of the possibility of his daughter posing for nude photos. "I've said that if Ivanka weren't my daughter, perhaps I'd be dating her." And the creepiness doesn't stop there. During a 2015 interview with Rolling Stone, Trump reportedly told the interviewer, "Yeah, she's really something, and what a beauty, that one. If I weren't happily married and, ya know, her father . . . ," in reference to Ivanka.

Donald Trump reportedly begged Ivanka to attend his campaign announcement

Donald Trump reentered the world of politics once again in November 2022 when he announced he would be running for U.S. president in 2024. Although Trump's kids are usually by their father's side, Ivanka Trump and Donald Trump Jr. were nowhere to be found during the announcement. It turns out that Trump Jr. couldn't attend because he was on a hunting trip at the time, while Ivanka seemingly wants nothing to do with politics, per The Independent.

Ivanka shared a statement with CNN regarding her absence, and it appears that she won't be nearly as involved with her father's campaign this time around — if at all. "I love my father very much. This time around I am choosing to prioritize my young children and the private life we are creating as a family," she revealed. "I do not plan to be involved in politics. While I will always love and support my father, going forward I will do so outside the political arena. I am grateful to have had the honor of serving the American people and I will always be proud of many of our Administration's accomplishments." Ivanka's decision might indicate how she feels about her father's return to politics, or maybe she just wants to distance herself from the chaos. Regardless, Donald Trump appears to have lost one of his cheerleaders.

Did some Trump family members date Secret Service agents?

A book by author Carol Leonnig alleges that two members of the Trump family were involved in forbidden love affairs with secret service agents. Of course, these allegations can't be confirmed as facts, but they certainly are intriguing. The book, titled "Zero Fail: The Rise and Fall of the Secret Service," claims (via The Guardian) that Donald Trump Jr.'s ex-wife, Vanessa Trump, formed a romantic relationship with a secret service agent who wasn't specifically assigned to her at the time. This detail may have protected the alleged couple, because, according to Leonnig, the agent didn't face consequences for the relationship. Personal relationships between agents and those in the White House are usually not allowed.

Vanessa allegedly wasn't alone in her secret search for love. The book claims that Tiffany Trump also dated an agent. Vanessa and Donald Trump Jr.'s marriage had been on the rocks long before their divorce and the secret service scandal that followed, per People. Vanessa reportedly found flirty text messages between Trump Jr. and former "Celebrity Apprentice" contestant Aubrey O'Day back in 2012.

Donald Trump Jr. always comes to his father's defense

Donald Trump Jr. has come to his father's defense in some of his most controversial moments. Let's revisit some of Trump Jr.'s most cringeworthy justifications for his father's behavior, shall we? Back in May 2022, former U.S. Defense Secretary Mark Esper came forward to reveal that Donald Trump suggested launching missiles into Mexico to target drug cartels during his time as president. "The president pulls me aside on at least a couple of occasions and suggests that maybe we have the U.S. military shoot missiles into Mexico," Esper said during an appearance on "60 Minutes." "I'd say, 'Mr. President, you know, I understand the motive,' because he was very serious about dealing with drugs in America. 'I get that, we all understand.' But I had explained to him, we can't do that. It would violate international law. It would be terrible for our neighbors to the south. It would, you know, impact us in so many ways."

Trump Jr. took to Twitter to defend his father following these shocking allegations, writing, "I'm still trying to figure out the recent media outrage about my father possibly wanting to target Mexican drug cartel manufacturing facilities in Mexico... Is that supposed to be a bad thing???" On a separate occasion, he seemingly attempted to rationalize his father's decision to praise Vladimir Putin and Kim Jong Un.

Donald Trump is proud of Tiffany Trump 'to a lesser extent'

Over the years, tabloids have dubbed Tiffany Trump the forgotten Trump child. Unfortunately for Tiffany, Donald Trump has jokingly taken jabs at her over the years, so this probably doesn't help. During an appearance on "Fox and Friends" in November 2016 (via Factbase Videos), Donald suggested he wasn't as enthusiastic about Tiffany's accomplishments as he could've been. "I'm very proud of my children," the former U.S. president said while calling into the show. "I mean, I'm just looking at them right now, as an example for your show. But I'm very proud, because 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 has also been so terrific."

It seems that Tiffany has never really been her father's favorite child. A leaked clip from "The Howard Stern Show" even revealed that her siblings allegedly advocated for her to be removed from her father's inheritance, according to Newsweek. This appears to align with claims an anonymous source made to People in 2017. "She says she is not guaranteed anything, which is one of the reasons Tiffany and Marla have been so respectful of her dad and tiptoed around so much," the source alleged.

Melania Trump doesn't seem to be a fan of Donald Trump's affection

Donald and Melania have had a lot of cringe-worthy moments of their own, and many revolve around Melania not being a fan of PDA — at least not when it comes to holding hands or locking lips with Donald Trump. A clip shared by The Independent in 2018 shows the seemingly not-so-happy couple standing alongside French President Emmanuel Macron and his wife Brigitte. Donald makes multiple attempts to hold Melania's hand, most of which she blatantly ignores.

A separate clip shared by The Independent documents the viral moment in 2020 when Melania seemingly refused to hold Donald's hand while exiting a private plane. The former president again tries grabbing his wife's hand on numerous occasions, but she pulled away every time. Perhaps she just isn't the affectionate type. Or, maybe Donald's controversial presidency took a toll on the relationship because Melania also yanked her hand away following the 2020 presidential debate between Joe Biden and Donald Trump. This time, the then-first lady didn't try to make her frustrations subtle. Instead, she pulled her hand away from Donald with quite a bit of force.

Donald Trump wasn't exactly a gentleman on Inauguration Day

The Internet pointed out the difference in the way Donald Trump and Barack Obama treated their spouses during their inaugurations. In a side-by-side clip of both moments shared by Us Weekly, you'll see that Barack waits for wife Michelle to exit the car so that they can walk side by side. In contrast, Donald got out of the car without Melania and seemingly had no problem walking ahead of her as she fell behind.

It has been suspected for years that there is a lack of love between Donald and Melania, and in 2018, a book by former White House aide Omarosa Manigault Newman further fueled these rumors. In the book, titled "Unhinged: An Insider's Account of the Trump White House," Newman alleged that Melania planned to divorce Trump at the end of his term. She claimed that the then-first lady chose to wait because she feared Trump would tamper with her citizenship. "If Melania were to try to pull the ultimate humiliation and leave him while he's in office, he would find a way to punish her," she wrote. "This is a man who has said he could pardon himself from the Mueller investigation. Why not pardon himself over an alleged visa payoff?" Well, Melania and Donald are still married as of this writing, so the reason for their lack of affection remains a mystery.