Major Red Flags In The Trump Family's Dynamics

Donald Trump's relationships with his kids and wives have long been a source of fascination. His extramarital activities, both rumored and confirmed, earned him frequent tabloid appearances, which was distressing for his heirs. And because the real estate mogul wasn't the most attentive parent during his heyday as one of Page Six's star attractions, the foundations of his relationships with his children were already on shaky ground.

Donald's second-oldest son, Eric Trump, admitted his dad wasn't around much during his childhood while praising his older brother, Donald Trump Jr., as a father figure. "In a way, he raised me. My father, I love and I appreciate, but he always worked 24 hours a day," Eric said in a 2006 interview with The New York Times. Meanwhile, Donald Jr. told New York magazine he refused to talk to his dad for an entire year after Donald cheated on his mom, Ivana Trump, with Marla Maples. Donald's daughter with Maples, Tiffany Trump, didn't even have the opportunity to give him the silent treatment. "As far as time, it was just me," Maples told People of her disproportionate co-parenting relationship with Donald. Then there's Ivanka Trump. Long considered Donald's favorite, fissures appeared in her relationship with him after the Trumps entered the political sphere.

There have been signs that the state of Donald's union with Melania Trump isn't great, either. She once told Parenting magazine that Donald didn't even perform one diaper change when their son, Barron Trump, was a baby — one of many red flags that the Trumps don't always prioritize familial bonds.

Because Donald Trump is a billionaire, you'd expect him to lavish his loved ones with high-priced gifts during the holidays. However, for him, it seems the season of giving is the season of regifting. "I'm the namesake, so I got re-gifted all the things that were monogrammed for him at times," Donald Trump Jr. told Extra. This led to an awkward moment during one Christmas celebration when Donald Jr. called his dad out for being a regifter. Upon opening a present, he recalled telling the elder Donald, "I know you didn't get this ... Because I gave it to you last year." 

In a video on her YouTube channel, Donald's niece, Mary Trump, said she suspected that a gift basket she received from her uncle and his then-wife, Ivana Trump, one year was also regifted. "There was clearly something missing ... there was an indentation where something should have been," she said. She later determined that the removed item was likely a container of caviar.

Another sign that Trump holiday events aren't the highlight of the year for some family members was Ivanka Trump and Jared Kushner's absence from Donald's big New Year's Eve bash at Mar-a-Lago in 2024. Then there are the Trumps' potentially telling social media posts. In 2021, Melania Trump failed to mention her husband in her Valentine's Day tweet, and Donald returned the favor in 2023 when he left Melania out of his Mother's Day message. The mothers of "Radical Left Fascists" did get a Truth Social shoutout, however.

While Ivanka Trump's husband, Jared Kushner, got in Donald Trump's good graces enough to land a role as one of his senior advisors during his first term as president, there was reportedly a time when Donald felt that Jared just wasn't son-in-law material. According to author Vicky Ward, Donald used to complain to friends that he wished Ivanka had married former New England Patriots quarterback Tom Brady instead. In her book, "Kushner Inc.," Ward wrote that Donald even joked to the Patriots' owner, Robert Kraft, "Jared is half the size of Tom Brady's forearm."

New York Times journalist Maggie Haberman shared another anecdote about Donald poking fun at Jared's size in her book, "Confidence Man." Upon learning that Jared and Ivanka were going camping, Donald reportedly joked about a movie in which a male character gets sexually assaulted during a camping trip. "Can you imagine Jared and his skinny a** camping?" he stated. "It'd be like something out of 'Deliverance.'" According to Haberman, he also said of Kushner's voice, "He sounds like a child."

On his podcast, "Political Beatdown," Donald's ex-attorney Michael Cohen revealed that another in-law his former boss used to detest was Eric Trump's wife, Lara Trump. "Not only did Donald make fun of her looks, but so, of course, did Don and Ivanka," Cohen said. He added that Donald had hoped Eric would marry one of his employees instead of Lara.

In a 2020 episode of his "Triggered" podcast, Donald Trump Jr. jokingly asked his dad, "Which is your favorite Trump child, and why is it Ivanka?" While Donald Trump insisted that he loves all of his children equally, it's not like he swore it on one of his God Bless the USA Bibles (available for the low, low price of $59.99), and it was once a universally accepted tidbit of Trump lore that Donald placed Ivanka on a pedestal. Then the Trumps decided to trade real estate for affairs of state.

Politics seemingly drove a wedge between Ivanka and Donald, with Maggie Haberman writing in "Confidence Man" that Donald once considered firing her and Jared Kushner from their White House roles via tweet. The relationship between father and daughter further deteriorated during the House's investigation of the U.S. Capitol riot. After Ivanka testified that she didn't believe the 2020 election was stolen from her father via fraud, he seethed on Truth Social, "Ivanka Trump was not involved in looking at, or studying, Election results. She had long since checked out."

Donald was right about his daughter checking out. In 2023, Ivanka announced she was finished working with her father in politics. "It's a pretty dark world. There's a lot of darkness, a lot of negativity," she later said on "The Lex Fridman Podcast."

Melania Trump's campaign trail absence ahead of the 2024 election fueled speculation that she didn't back her husband's battle for another presidential term. However, you get what you give — and it seems Donald Trump isn't the most supportive spouse, either. In her memoir, "Melania," the former model recalled the only words of advice and encouragement her husband offered her regarding her role as first lady the first time around: "Good luck."

Melania desperately tried to glean some deeper sentiment from that flippant phrase. "I realized he wasn't worried, he was proudly confident I could handle the future," she reasons. "It was his unique way of saying, 'Good luck — I know you'll excel. Let's get started.'"

Donald may remain unenlightened about Melania's musings on the inner workings of his mind, as he admitted that he hadn't read her book during a 2024 campaign rally. "I hope she said good things about [me]," he told his supporters. He did, at least, encourage the rallygoers to purchase copies of the memoir, but revealed his willingness to torpedo sales in the name of vanity. "And if she says bad things about me, I'll call you all up and I'll say, 'Don't buy it. Get rid of it,'" he added.

Another sign that politics and marital bliss don't mix for the Trumps is Melania Trump's thoughts about some of her husband's behavior on the campaign trail. During a 2023 rally in Iowa, Donald Trump revealed that she dislikes his signature dance move: waving his fists around in the air like he just doesn't care about looking ridiculous. Donald briefly seemed to forget who was the star of his Melania anecdote when he tried to insert his favorite honorific into it. "She said, 'Sir,'" he recalled before correcting himself. "No, she said, 'Darling, I love you, I love you, but this is not presidential. You don't dance off the stage.'"

Donald also revealed that Melania dislikes it when he makes like a struggling comedian desperate for any form of relevancy and mocks trans athletes. "She says, 'Darling, I love you so much, but this is not presidential when you do the weightlifting ... or when you do the swimming thing," he told his audience.

According to Melania, Donald's campaign antics aren't the only area where they aren't on the same page politically. In her memoir, she revealed she doesn't share his views on abortion and is pro-choice. She also wrote, "Occasional political disagreements between me and my husband were part of our relationship."

During primary season in 2024, Donald Trump celebrated one of his victories by rattling off the names of his most helpful relatives during a speech. While she would never make it to the altar with Donald Trump Jr., even Kimberly Guilfoyle got a shoutout. However, Donald didn't mention Eric Trump or his wife, Lara Trump.

It's highly unlikely that Lara will ever forget her father-in-law in a similar manner. In her mind, he's achieved saintly status. Of Donald's election victory, she told PragerU, "I'll give it to God and Donald Trump; they did it. ... I don't think there's any doubt that God had a hand in this." She added that Donald plans on using his divine power to "save the world." Apparently, Lara also thinks that halo looks pretty good on him — but it doesn't make him humble. "Donald Trump is very good-looking. He'll be the first to tell you that," she said in an NBC News interview.

Lara adores her daddy-in-law so much that the centerpiece of her 40th birthday party was a table piled high with rainbow-colored Trump hats. She also couldn't contain her excitement when rapper Forgiato Blow let her borrow his massive gold chain adorned with Donald's likeness. She later wore it for an appearance on "The Benny Show" and gushed, "It's been the greatest movement in American political history and we're never going to see another Donald Trump."

There was a time when Donald Trump Jr. was desperate to spend time with his dad. In his book, "The Art of the Deal," Donald Trump wrote about his son, "I tell Donny I'll be home as soon as I can, but he insists on a time. Perhaps he's got my genes: the kid won't take no for an answer." But it seems the allure of hanging out with his pops started wearing off for Donald Jr. after he learned his family would be returning to the White House.

Donald Jr. ended 2024 by moaning about having to attend his father's New Year's Eve party at Mar-a-Lago, which coincided with his birthday. "It's sort of like amateur night ... I get to be around a thousand drunk people giving me their political opinions that I don't necessarily want to hear," he lamented on "Triggered," adding that the whole Mar-a-Lago vibe just isn't for him — he's more of an outdoorsy type.

Donald Jr. further complained that his dad's pals treat him like he's clueless and in need of their guidance. "This'll be like year nine of, 'Hey, you know, have you ever thought to maybe have your dad not tweet that?'" he groused. "I'm like, no, I've never thought that 'cause I'm a freaking imbecile." When dishing on what Donald really thinks about his kids, Michael Cohen claimed "The Apprentice" alum also finds Donald Jr.'s intelligence lacking. "These are Donald's words: that Don Jr. has the worst f***ing judgment of anyone he's ever met in his life," he said on "Political Beatdown."

Donald Trump has committed an egregious etiquette breach twice by stealing big moments from mothers-to-be in his family. When he was running for president in 2016, Lara Trump spent months campaigning for him while she was pregnant. It was the first time she and Eric Trump had a baby on the way, and naturally, the couple was excited to privately reveal to their family on Inauguration Day that Lara was with child.

Lara and Eric could have had a lot of fun dreaming up a MAGA-themed reveal for their family's fans, but Donald ruined the surprise by announcing to a crowd backstage that the couple was expecting. "He told everybody that was in the room, and I was like, 'We haven't told anybody yet!'" Lara recalled on "Fox & Friends" (via The Washington Post).

Donald similarly spilled the beans about Tiffany Trump's first pregnancy in 2024, totally disregarding how she and her husband, Michael Boulos, might feel about him sharing their happy news with the world before they were ready for everyone to know about it. The way Donald announced it was also lackluster for someone who prides himself on being a showman. "She's an exceptional young woman. And she's going to have a baby," he said at a Detroit Economic Club Luncheon. "So that's nice."

Donald Trump will shamelessly promote anything — on Truth Social, he tried to make a quick buck before the holidays by touting his pricey Bibles as the "perfect" Christmas gift. But when Donald Trump Jr. agreed to propose to Vanessa Trump at a jewelry store in exchange for a free ring, that was too tacky even for him. On "Larry King Live" (via E! News), Donald recalled the scolding he gave his son: "You have a name that is hot as a pistol, you have to be very careful with things like that."

When Donald Jr. allegedly had an affair with Aubrey O'Day, Donald reportedly intervened in his son's love life. "He was the one who pressured Jr. to stop seeing Aubrey," a source told Us Weekly. The insider added that Donald Jr. didn't end his marriage to be with O'Day because he didn't want to displease his father. However, according to the Daily News, Donald's meddling didn't work when he tried to convince Donald Jr. and Vanessa not to get a divorce in 2018. "He's personally upset," a source said.

Donald later helped Donald Jr. deal with another messy romantic entanglement by offering his son's ex, Kimberly Guilfoyle, an ambassadorship in Greece that will keep her far away from Donald Jr. and her replacement, Bettina Anderson. Apparently, Donald Jr. was thinking of his father when he started romancing the socialite. A source told People, "Don Jr. has always wanted to look good in his father's eyes. Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him."

Donald Trump has a long history of acting inappropriately toward Ivanka Trump. One of the best examples of his worst behavior was when he appeared on "The View" (via Today) in 2006 and said, "She does have a very nice figure. I've said if Ivanka weren't my daughter, perhaps I'd be dating her." According to former Miss Universe Brook Antoinette Mahealani Lee, Donald also gave her the ick by gushing about Ivanka's appearance at the 1997 Miss Teen USA pageant. Speaking to The New York Times, Lee recalled Donald asking her, "Don't you think my daughter's hot?" At the time, Ivanka was 16 years old.

Tiffany Trump was even younger — a mere baby — when Donald started making disturbing remarks about her body. "She's got Marla's legs. We don't know whether or not she's got this part yet but time will tell," he said on "Lifestyles of the Rich and Famous" (via People). The "part" of Tiffany's mother, Marla Maples, that Donald was referring to was her breasts.

Donald Trump Jr. followed in his father's skeevy footsteps ahead of the 2024 Republican National Convention when he used an eyebrow-raising adjective to describe his daughter, Kai Trump. In a TikTok video, he said to the 17-year-old, "[Will] getting makeup make me look sexy like you?"

Donald Trump discovered that his youngest son, Barron Trump, was a useful political tool during the 2024 presidential election. He revealed that Barron was responsible for encouraging him to appear on the shows of podcasters and streamers popular with young men, including Adin Ross, who has platformed neo-Nazis and white supremacists. "[Barron is] a big fan of yours," Donald told Ross.

Another sign that Barron was preparing to enter the political arena was when it was announced that he would be a Florida delegate at the RNC. However, Melania Trump's office later issued a statement to ABC News and other outlets that read, "He regretfully declines to participate due to prior commitments." This move suggested that Melania and Donald might not be on the same page when it comes to Barron's political future.

Then there are the reports that Melania plans on being a "part-time first lady." A source told the New York Post that she wants to spend some of her husband's second term in NYC — where Barron happens to be attending college while residing in Trump Tower. This arrangement would allow Melania to keep a watchful eye on Barron while both of them avoid all the chaos Donald unleashes in D.C. A source told People, "Barron already has his own political ideas. It all needs to be monitored in light of the situation ... Melania feels it's better to be around him as much as possible."