Big Name Celebs Who Turned On Donald Trump Once He Entered Politics

Before he became one of the most polarizing figures in modern politics, President Donald Trump was a familiar presence in celebrity social circles. A business mogul from New York whose enterprises covered everything from real estate to the media and everything in between, he was a fixture at high-profile events — from the Met Gala to Fashion Week shows to exclusive film premieres — and forged A-list friendships that seemed to have been built on shared power, glamour, and influence.

Politics, however, reshuffled some dynamics. When Trump's presidential ambitions took center stage in the 2010s and he began transitioning to his new life as a political lightning rod, many of the acquaintances he had accumulated during his years as a larger-than-life, multi-hyphenate businessman began coming apart at the seams. Some distanced themselves from the controversial politician discreetly, while others did it vociferously. 

For most, this severance from the U.S. president happened along ideological lines. And it was all the more pronounced in an era where social media-driven optics can make or break a reputation. Big-league actors, music industry heavyweights, television icons, and other celebs who once rubbed shoulders with Trump rewrote the terms of their associations with him after he accelerated his bids for the presidency. 

Rearranged though they might be today, those past friendships remain recorded in the pages and photos of Hollywood history. Here are some major celebs who turned on Trump after he entered politics. 

George Clooney has been a longtime Democrat, so it's hardly a surprise that he's not a cheerleader for President Donald Trump. But one of the lesser-known details about the "Three Kings" star, which still takes fans by surprise, is that his connection with the U.S. president transcends the latter's political career. The Hollywood star and the politician were once part of the same industry, when Trump, during his businessman days, moved among the who's who of the entertainment world as one of their own. 

"I knew him very well," Clooney told Variety, revealing that the two were seemingly friendly before Trump went neck deep into Republican politics. "He used to call me a lot, and he tried to help me get into a hospital once to see a back surgeon. I'd see him out at clubs and at restaurants. He's a big goofball. Well, he was. That all changed." Further on in the interview, Clooney's takedown of Trump was more expletive-laden than his nostalgic musings. 

At the same time, it's not as if the president has been at all subtle in his criticisms of Clooney. On Truth Social, the social media platform Trump owns, Trump has been waging a long-drawn-out war of words on Clooney. Calling him a "fake movie actor ... who never came close to making a great movie," the president's tirade against Clooney hardly betrays their friendly past (via The Guardian).

The Met Gala and President Donald Trump may seem like polar-opposite concepts. But there was once a time when Vogue chieftain Anna Wintour and the U.S. president shared a friendly relationship. Trump even attended the Wintour-led fundraiser for decades, before the doors were allegedly closed on him. In fact, it was at the Met Gala in 2004 that he proposed to his now-wife Melania Trump, and when the pair tied the knot a year later, Wintour partook in their wedding celebrations. 

Wintour and Trump's dynamic began visibly weakening with the businessman's slide into politics during the 2010s. Rumor has it that the souring relations between the fashion editor and America's first family hinged partly on a fallout with Melania, whom Wintour didn't seem to favor on Vogue covers as much as she did Trump's first wife Ivana Trump. However, some commentators suggest that the Wintour-Trump clash goes beyond the reductive catfight narrative. 

"It's about politics. It's about abortion rights and women's rights and LGBT rights ... you can't behave like that and think you'll ever be on a Vogue cover," journalist Bronwyn Cosgrave, who worked at Vogue, told The Telegraph. While the president and Wintour reportedly made contact multiple times after he first won the election in 2016 — and Wintour even visited the White House — she has spoken sparingly on the subject of Trump, besides publicly declaring that he wasn't welcome at the Met Gala anymore. 

One of the most famous people from President Donald Trump's past who is prominently absent from his orbit today is Oprah Winfrey. The legendary television host — who is politically independent but known for her liberal takes on global issues — perceptibly detached from the once-friendly associations she shared with the polarizing president when his foray into politics began. In fact, Trump was able to date their rupture to the time he entered the 2016 presidential race. 

"Once I ran for office she diverged ... [she] has been down to Mar-a-Lago," Trump told an audience while campaigning in Georgia (via Variety). "We had a good relationship. I like Oprah." That last compliment — notably delivered in the present tense despite their alleged falling out — doesn't register as too jarring, considering that Trump has been relatively mellow in his critiques of Winfrey compared to his other detractors. 

Their relationship goes back to at least the 1980s, when Trump began appearing on Winfrey's then-new talk show. Such was Trump's adulation for her that he even famously remarked on "Larry King Live" in 1999 that if he were ever to choose a potential running mate for his presidential candidacy, he would pick Winfrey (via YouTube). "She is a terrific woman. She's somebody that's very special," he gushed. Winfrey, meanwhile, hasn't been too emphatic in either her praise or criticism of Trump and has largely made her allegiances clear by showing support for his Democratic opponents. 

To say that Ellen DeGeneres and President Donald Trump were once buddies might be a bit of a stretch. But one can safely say that the pair were at least friendly until a few years ago. The U.S. president appeared on the television host's namesake program when it first premiered in the early 2000s, featuring in the earliest two seasons of "The Ellen DeGeneres Show." In fact, during his second appearance, he was joined by his then-recent fiancée, Melania Trump. 

At the time, Trump hadn't formally entered politics and was still dabbling in various business ventures such as real estate and productions like "The Apprentice." And DeGeneres, even as a newbie, carried the same easygoing charm that came to endear her to millions when she became television royalty. Together, Trump and DeGeneres made an entertaining pair to watch in that era of programming. 

Cut to two decades later, and DeGeneres has joined a league of celebs who left America to escape Trump's presidency. While the internet theorized about DeGeneres' dramatic relocation — especially in light of the string of controversies that marked her downfall from fame — the comedian confirmed that it was indeed the Republican president who had inspired it. Her exaltation of Trump on her own show, all those years ago, now reads like an ironic punchline she might want to retract: "[Y]ou are an inspiration because you really do represent what everyone is trying to achieve" (via YouTube).

Donald Trump and Martha Stewart's beef goes back to a time long before politics entered the picture and soured things further. The two business honchos — both with their own versions of the reality show "The Apprentice" — seemed to have been quite pally with each other before television ratings and competitive clashes ruptured whatever connection they shared during the early 2000s. During their friendlier years, Trump and Stewart were photographed together on multiple occasions, crossing paths as elites on New York's social circuit. 

Things began spiraling downward when, in 2005, a spin-off of the business-based show that Stewart was hosting failed to live up to its hype and flopped hard. Aggrieved over the slipping ratings of his iconic show, Trump lashed out at the multi-hyphenate media mogul. "Your performance was terrible in that the show lacked mood, temperament, and just about everything else a show needs for success. I knew it would fail as soon as I first saw it," he said in a letter at the time (via CBS News). 

A sharp-tongued back-and-forth persisted between the former pals in the media during the aughts. The sensational feud eventually piped down, and Trump and Stewart even appeared to have smoothed things over by smiling for photographs together again and issuing affectionate social media shout-outs. However, after Trump won the election in 2016 and then again in 2024, Stewart made it clear that there was no love lost between them by showing unequivocal support for the Democrats.

In recent times, it seems like Whoopi Goldberg has only harsh words for President Donald Trump and wouldn't want to be anywhere near the controversial leader. Decades ago, though, things were slightly different between them. As entertainment figures and fellow New Yorkers, Trump and Goldberg crossed paths fairly often, even co-starring in '90s films like "The Little Rascals," "Eddie," and "The Associate." It was only when Trump was toying with the idea of the presidency that signs of strain between the acquaintances became publicly visible. 

In 2011, Trump stopped by "The View," then hosted by Goldberg, Barbara Walters, and other firebrand women. Unsurprisingly, his politics didn't align with those of many on the panel, but he appeared to hit a nerve with Goldberg, particularly during one segment in which he petitioned for then-President Barack Obama to present his birth certificate as proof of his American citizenship. "Donald, I love you ... I think that's the biggest pile of dog mess I've heard in ages. ... It's not because he's Black, is it?" Goldberg hit back (via YouTube). 

In a later explanation issued on "The View," Goldberg mentioned how she was "not a fan" of Trump and his rhetoric, and that his turn to politics provided her with an outlet of sorts to air her grievances about him. Trump's own opinion of the comedian hasn't been too buoyant lately, either, and the U.S. president lambasted her and her work at a rally in 2024: "What a loser she is" (via X). 

There are plenty of celebrities who share close connections with the Trump family, but owing to President Donald Trump's often controversial politics, many big names avoid publicly acknowledging those ties. Entrepreneur and hip-hop magnate Russell Simmons, however, has been more than willing to not just reminisce about the good times he has spent with his pal, but also school him on the more contentious aspects of his leadership. 

"That was my man," Simmons said on "In Depth With Graham Bensinger," enthusiastically talking about his frequent visits to Mar-a-Lago with Trump. "I would talk all the time to Donald. ... We had all kinds of fun stuff we did together." He went on to explain then how his own politics didn't align with Trump's, unapologetically recalling the infamous remark he made when his friend joined the presidential race in 2015: "I'd rather Kim Kardashian be president than Donald Trump." 

Simmons' comment apparently caused a rupture in the decades-long friendship he had shared with Trump up until that point. However, it didn't stop the Def Jam founder from continuing to give Trump a piece of his mind — as bluntly as only friends can. "Stop the bulls***. Stop fueling fires of hate. ... You're smarter and certainly more loving then you let on," he wrote in an open letter on Globalgrind. "[I] will be campaigning rigorously against you. But if you win, I might still accept an invitation to your house to straighten you up every so often." 

Arnold Schwarzenegger has been a politician for much longer than Donald Trump has, having notably served as the governor of California between 2003 and 2011. And considering that the two big shots are both Republicans and have been friendly in the past — Schwarzenegger even appeared on "The Apprentice" — one would think that they might have exchanged notes when Trump entered the political arena. That couldn't have been further from the truth. 

During the 2016 election, Schwarzenegger made his stance on Trump known with a staggering statement (via X): "For the first time since I became a citizen in 1983, I will not vote for the Republican candidate for President ... there is one label that I hold above all else — American." He went on to urge people: "[I]t is not only acceptable to choose your country over your party — it is your duty." 

Interestingly, Schwarzenegger had, by then, been appointed the host of "The New Celebrity Apprentice," which Trump was originally supposed to lead. While the "Terminator" star's disagreements with Trump didn't initially seem to cause a break in his plans, and Schwarzenegger did fulfill his commitments to the show, he apparently wasn't able to pull good ratings and eventually bowed out — but not without exchanging a barrage of jabs with Trump. Their squabble has continued since, culminating in Schwarzenegger's shocking endorsement of Democrat Kamala Harris for president. 

Ja Rule has openly used the H-word (hate) for President Donald Trump in light of his politics, but there was once a time when the rapper wasn't so antipathetic to the politician. Back in 2015, when the real estate mogul had just kick-started his political career, his unfiltered candor and no-holds-barred speech — which have since become points of derision among his detractors — seemed to have appealed to Ja Rule, who knew him socially during the 2000s. 

Calling the then-future U.S. president "entertaining," the "Always on Time" hitmaker told Rolling Stone: "He speaks very openly and candidly about what he feels. I think it's a breath of fresh air for everybody to hear it." While Ja Rule did express some dissonance with Trump's beliefs, even going so far as to call him "crazy," he established a kinship of sorts with him by recognizing him as one of their own. "He has always been an outspoken person. I'm not shocked by anything that comes out of his mouth at all. He's like a rapper." 

When Trump's ideologies stopped being abstract concepts and actually began showing up in actionable policies after he became president, he appeared to fall out of favor with Ja Rule. Even so, the rapper welcomed Trump with (partially) open arms to use his celebrity app Iconn in 2021, when major platforms within the social media ecosystem ousted him in light of the January 6 Capitol attack. "It's freedom for everybody," he told TMZ. 

Before his politics divided Hollywood, President Donald Trump was a welcome regular on the entertainment circuit. One of the many celebrities who came into his social orbit during those years was Demi Moore. The "Ghost" star, who was just coming off her '90s peak, was easily one of cinema's biggest stars at the time. And while there is no evidence to show that she was chummy with Trump, an acquaintanceship, at the very least, can be inferred from their joint appearance at the launch of a Trump hotel in 2008. 

The event, held in New York, had many high-profile names in attendance, and Moore stood out among them most in a striking ultramarine blue dress. For what it's worth, there is also a picture of Trump and Moore puckering up before the cameras (and Melania Trump) to share a kiss. Of all the Moore's controversial moments, she would likely prefer to leave this one quietly behind in the millennial archives, when Trump's political career hadn't yet begun. 

Though Moore has largely remained tight-lipped about her politics, it's not been hard to deduce her liberal leanings from her support for Democratic politicians and disavowal of conservatism. "America is built on Puritans, religious fanatics, and criminals ... you're kind of seeing [as much] in our election right now," she said during a public appearance during the 2024 U.S. election (via Variety). In the past, Moore has also distanced herself from her ex-husband Bruce Willis' Republican support.