Celebs You Didn't Know Were Connected To The Trumps

According to The Atlantic, Donald Trump first gained national attention when he sat down with Tom Brokaw to talk real estate in 1980 at the age of 33. In the decades since, Trump amassed a longer list of acting credits than most working thespians, got shouted-out by your favorite rapper at least once, and appeared on more talk shows than a couch. Oh, and he got elected President — you might have heard. Naturally, Trump met a few people along the way. "I have many friends. Many, many friends," Donald Trump is fond of saying. Believe it or not, this is true.

We all know about Trump's former friendship with Bill and Hillary Clinton, but did you know Ivanka Trump attended Natalie Portman's wedding? Or that Paris Hilton voted for Trump because "[she's] known him [her] entire life"? What about the time Topher Grace dated Ivanka? But as the saying goes, friends come, and friends go. Here are celebrities you didn't know were connected to the Trumps.

Tom Brady

While there is much debate on whether or not New England Patriots quarterback Tom Brady is the greatest quarterback of all time, there wasn't much debate on who he was throwing his support behind during the 2016 presidential election. After a game in Sep. 2015, a MAGA hat was spotted in five-time Super Bowl winner's locker. When asked by reporters if Trump could pull off an election upset, Brady replied, "I hope so. That would be great. There'd be a putting green on the White House lawn, I'm sure of that."

Brady then spoke to Boston's WEEI (per Politico), revealing the pair have been friends since 2002. "I mean it's pretty amazing what he's been able to accomplish," he said. "He obviously appeals to a lot of people, and he's a hell of a lot of fun to play golf with." He continued (per USA Today), "Like I said, he's been a friend of mine, supported our team. He's been on the Patriots sidelines a lot and always called me after games to encourage me over the course of 15 years. And, you know, so that's kind of the way it is."

After a judge overturned Brady's four-game suspension for the Deflategate scandal, the president-to-be congratulated his golfing buddy on Twitter. "Congratulations to Tom Brady on yet another great victory- Tom is my friend and a total winner!" he tweeted.


Donald Trump is just like us — he loves Oprah. During an Oct. 7, 1999 interview on Larry King Live (during the many times he floated the idea of running for the seat in the Oval Office), the real estate mogul claimed that Oprah would be his ideal running mate. "I love Oprah. Oprah would always be my first choice," he said. "She is a terrific woman, she's somebody that's very special. ... If she'd do it, she'd be fantastic. She's popular, she's brilliant, she's a wonderful woman."

In 2015, Trump told ABC News' George Stephanopoulos that if he chose Oprah as his Vice President "we'd win easily." He then offered her another overwhelming ovation, noting, "She's a friend of mine, she's a good person. I've been on her show. ... I like Oprah, I mean, is that supposed to be a bad thing?" Trump also regularly shows Oprah love on social media, calling her "terrific" and proclaiming, "I adore Oprah."

Oprah and Trump discussed his presidential ambitions on her show way back in 1988. "I know people have talked to you about whether or not you want to run, would you ever?" she asked. Trump answered that if he did run and win, "[the country] wouldn't be the way it's been, believe me." We can't say he didn't warn us.

Chelsea Clinton

Per Politico, Chelsea Clinton and Ivanka Trump met through their husbands and "clicked immediately." The pair's relationship was red carpet camera-ready, with the first daughters' love fest at the 2014 Glamour Women of the Year Awards was on full display. There is a reason why the two instantly became friends. "There's so much that they understand about each other," Washington Post columnist Emily Heil told CNN. "If there's anyone who understands what Chelsea Clinton has been through it is Ivanka Trump."

In a February 2015 profile of Ivanka in Vogue, Chelsea heaped praise on her friend, even comparing her personality to that of her father, Bill Clinton. "She's always aware of everyone around her and ensuring that everyone is enjoying the moment," she said. "It's an awareness that in some ways reminds me of my dad, and his ability to increase the joy of the room. There's nothing skin-deep about Ivanka." In a 2016 interview with Cosmopolitan, Chelsea said, "I am absolutely friends with Ivanka and I am grateful for her friendship. And I'm always going to believe, because this is how my parents raised me, that friendship is more important than politics." Two months later, the friendship was reportedly "on ice."

After the 2016 election, Chelsea admitted to Stephen Colbert that she has "not spoken to [Ivanka] in a long time." She continued, "It's clear that she has supported policies and decisions that I don't agree with. I've been very vocal about my opposition to President Trump."

Anna Wintour

Longtime Vogue editor Anna Wintour was one of the many celebrities to attend Donald and Melania Trump's wedding in 2005. She was so close to the Trump family, in fact, that she offered Ivanka Trump a job. "Early one morning during finals, the phone rang... It was Anna Wintour, the editor in chief of Vogue. Anna is someone I've always admired; we met when I'd done some modeling as a teenager," Ivanka revealed in her book Women Who Work. "She'd heard that I was graduating soon. She knew I liked fashion. She wanted to offer me a job at Vogue."

Although Anna and Donald were also friends, their politics weren't as friendly. Anna has held fundraisers for both Barack Obama and Hillary Clinton, while not offering the same for Donald. Since the election, the friendship has cooled to the point of freezing. Donald, who has been a fixture at Anna's exclusive Met Gala for years, won't be invited back. During an Oct. 2017 appearance on The Late Late Show with James CordenAnna was asked which celebrity would never receive an invitation again. "Donald Trump," she quickly answered. 

Meghan Markle

The Duchess of Sussex Meghan Markle might be a Queen Consort (It's complicated.) one day, but once upon a time, Ivanka Trump was one of her idols. Back in 2014 on her now-defunct lifestyle blog The Tig (per The Mercury News), the former Suits star called Trump "staggeringly beautiful" and "so incredibly savvy and intelligent." She also praised the first daughter for "undoubtedly [creating] her own empire," and not just by using "her father's famed Trump notoriety."

The post eventually turned into an email exchange between the pair where Trump answered questions about her life. "She does it all," Markle said, admiring Trump's work/life balance and how she juggles "the line between letting yourself go or looking like you just stepped off a runway (or at least had the time to put some lipstick on)." The glowing review didn't stop there. "This much I know — when we have drinks, I will make sure I order whatever she does — because this woman seems to have the formula for success (and happiness) down pat," Markle continued.

We assume they never got around to those drinks, or if they did it was probably pretty awkward thanks to Markle's 2016 appearance on The Nightly Show with Larry Wilmore, during which she called Donald Trump "divisive" and "misogynistic."

Hugh Jackman

Wolverine and Ivanka Trump are "lovely" friends? Absolutely. Whether Trump and her husband Jared Kushner are hanging out at Hugh Jackman's house or attending his 50th birthday party, their friendship extends beyond her father's policies. "I've known those guys for 15 years, and we don't talk politics at birthday parties," Jackman told Variety in 2018 while promoting The Front Runner

The Les Misérables star's fans weren't thrilled about the friendship, so in an interview on The Howard Stern Show, Jackman defended his relationship with Trump and Kushner. "They're great friends. They're unbelievably loyal," he said (per E! News). "We're great friends, and I want to say to people ... 'So, if you're friends of 15 years' dad became president, do you dump them as a friend? Really?'"

However, at least one industry insider speculates that Jackman's friendship with Trump and Kushner could be a factor in The Front Runner's less than awesome reviews and poor box-office results. "Jackman has had a pretty much pristine reputation and is almost always well received," Danny Deraney, whose public relations firm represents many high-profile clients, said (per The Mercury News). "Despite that, the company you keep, no matter who you are or how great reputation is, can be perceived as a negative by the public or for that matter, adoring fans."

Emmy Rossum

Shameless star Emmy Rossum was one of the 500 guests to witness Ivanka Trump and Jared Kushner tie the knot in 2009. The pair then looked like BFFs at the Costume Institute Gala in 2010, and they even supported each other on social media — "Congrats Emmy on your new show Shameless. It is amazing, and you are great in it!" Trump tweeted in 2011.

Rossum even interviewed "her friend" for a Hamptons profile in 2013, and when she asked Trump about her favorite dishes, she replied, "I have a lot of light, refreshing dishes that I really enjoy making, especially when entertaining good friends, like you."

However, like many relationships with the Trumps, it quickly turned sour after Donald Trump was elected president. "This morning still sad. I was looking forward to the next 4 yrs. To having a child, maybe a daughter, under the first female president," Rossum tweeted the day after the 2016 presidential election. "I wanted to tell her she could achieve anything she wanted. That she would win if she led with kindness. Not to make fun of people. Or bully," she added. And when President Trump instituted a zero tolerance border policy that resulted in "more than 2,300 children [being] separated from their parents" and placed in detention centers, according to Yahoo, Rossum pleaded with her friend to step up and do the right thing. "@IvankaTrump this is a moral emergency. you can do something real," she tweeted. Awkward! 

Russell Simmons

"I was with him on his first date with Melania. We were friends for many years," entrepreneur and co-founder of Def Jam Recordings Russell Simmons told the New York Daily News in 2017. Revealing that he once spent "every weekend" with Trump at the president's Mar-a-Lago resort in Florida, Simmons stated, "We haven't been friends since the day he announced, and I said, 'I'd rather Kim Kardashian be president,' so he called the office and that was the end of our friendship."

In a 2015 open letter to Trump on Global Grind, Simmons wrote, "over 30 plus years you have been an amazing friend" and lamented the fact that Simmons' public comments about Trump's candidacy had "strained or ruined our friendship," but stated "what's at stake is bigger than us."

He urged Trump to "stop fueling fires of hate" and feeding "into the rhetoric created by small-minded people." He added, "You're smarter and certainly more loving then you let on. ... You have been many people's champ in the past, but now you are becoming a major embarrassment. I know the cheap seats are easy to play to, but you can get them just by being the man I have known for nearly 30 years." 

Mike Tyson

Donald Trump and the former heavyweight champion Mike Tyson's friendship goes back more than 30 years. In fact, Trump even remained one of Tyson's most vocal supporters through Tyson's 1992 rape conviction. During an interview that same year with NBC Nightly News (obtained by Buzzfeed), Trump claimed that Tyson was "railroaded in this case" and seemingly blamed the victim. "You have a young woman that was in his hotel room late in the evening at her own will," he said. "You have a young woman seen dancing for the beauty contest — dancing with a big smile on her face, looked happy as can be."

Speaking to Howard Stern in 1992 (per CNN), Trump called Tyson's conviction "a travesty." He added, "It's so sad because I've known Mike more or less from the beginning. He started off having his first fights at my place, and he's had his biggest fights at Trump Plaza in Atlantic City." He went on to tell Stern that he never saw any inappropriate behavior from Tyson, but he's seen "women going around touching him" on numerous occasions. "He walks in a room, and the women start grabbing him and grabbing his a** and grabbing anything else they can grab on him," he explained. 

It's unclear exactly how close Trump and Tyson remained in the following years, but when HuffPost Live asked Tyson decades later if Trump could count on his vote in 2016, he didn't hesitate: "Hell, yeah. Big time."

Karlie Kloss

Former Victoria's Secret Angel and current tech entrepreneur Karlie Kloss is not only friends with Ivanka Trump; they are sisters-in-law by marriage — Karlie married Joshua Kushner (Jared's brother) in Oct. 2018. "So much love for you both as you begin forever together," Ivanka tweeted after the nuptials.

Karlie and Ivanka attended the 2016 US Open together and even kicked it on billionaire David Geffen's $200 million yacht in Croatia. We assume politics aren't discussed much between the friends-turned-in-laws, as Karlie and Joshua are both openly liberal. "One of the greatest privileges we have as Americans is a voice. I'm proud to say I did my part, now it's your turn. #ImWithHer," Karlie posted on Instagram the day of the 2016 election. "It is no secret that liberal values have guided my life and that I have supported political leaders that share similar values," Joshua told Forbes in 2017. "But neither political party has a monopoly on the truth or on constructive ideas for our country. It's important to be open minded and learn from differing opinions." 

Larry King

Donald Trump has been a frequent guest on Larry King Live going all the way back to the 80s. Speaking to CNBC's "Squawk Box" in 2016, King revealed that those appearances yielded a friendship with the 45th president that also goes back decades. However, the legendary talk show host stated he would be voting for Hillary Clinton. "Some of [Trump's] stands, I just can't go with," he said. "When I'm down to the two, I would tell Donald, 'Donald, I love you. You're a great friend. But I can't buy some of the things [you've said],'" King continued.

In a 2017 appearance on MSNBC, King revealed he "hasn't heard from" Trump since the election. That might be for the best, as King's opinion of Trump seems to have slipped since he took over the Oval Office. Speaking with John Fugelsang on SiriusXM Insight, King called Trump's time in office "one of the most ridiculous presidencies I've ever seen." And when TMZ caught up with King and asked for his thoughts on his old friend, he said, "I don't know this Donald Trump, and I'm very, very sad." 

Regis Philbin

Legendary television personality Regis Philbin met Trump in 1983 and they have been friends ever since. "I think he's a great guy," Philbin said in a 2016 interview with Newsday

Speaking to CTV's Canada AM in January 2016, Philbin said Trump was "doing alright for himself," but noted Trump's inflammatory rhetoric on the campaign trail. "I wish he would calm down a little bit, but I'm not going to get involved." When asked if his friend would do well in the Oval Office, Philbin replied, "I think that he'll be on fire if he becomes president. It might be the best thing that ever happened ... for him and maybe for the country. We'll all find out together."

In 2017, TMZ caught the former Who Wants To Be A Millionaire host outside a restaurant in Hollywood. "I didn't believe it was going to happen, but he made it," Philbin said of Trump's stunning victory over Hillary Clinton. When asked if the businessman was good for the country, Philbin replied, "Well, so far, I think he's done quite well, don't you? He's getting things done that were never done before. Anyway, who knows? ... So we will see. I'll give him a little more time."