14 Surprising Celebrities That Have A Long History With Donald Trump.

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Mike Tyson

It may not seem like Hollywood has President Trump’s back these days, but politics aside, Trump has rubbed elbows with a bunch of A-list celebrities over the years. Then again, it’s impossible to ignore the massive influential sphere that The Donald has had among famous entrepreneurs, socialites, and Hollywood celebrities. So, while some celebrities distanced themselves from him since his presidential victory in 2016, some of the people on the list once had an awesome bond with the current president of the United States.President Trump and Mike Tyson go way back! The Donald was a big supporter of the boxer. Trump got to know Mike Tyson after he hosted the boxer’s matches at Trump Plaza in Atlantic City. But when Tyson was convicted of a serious crime in 1992, the future president stood by Tyson’s side and denounced the verdict as “a travesty.”
Doug Symington / CC BY 2.0

Kanye West

It’s well known that Kanye West worships the red carpet that President Trump walks on. Trump and Kanye met at the Trump Tower in New York right after the 2016 election. During their meeting, the two of them took a moment out of their equally busy schedules to talk about life. They’ve also been very vocal about their mutual appreciation for one another on social media.
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Russell Simmons

Entrepreneur Russell Simmons and Donald Trump were friends for years, but are they friends now? When Trump became president, his friendship to Simmons appeared to have taken a hit. In an open letter in December 2015, Simmons told Trump that: “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."
David Shankbone / CC BY 3.0

Barbara Walters

Everyone knows Barbara Walters accomplishments but not many know of her friendship with Trump. The world-renowned journalist has had an on-off friendship with Trump for years. Their connection took a hit when Walters supported Rosie O’Donnell’s criticism of Donald Trump in 2007. But two years later, Walters patched things up with Trump and even admitted she missed him.
John Mathew Smith / CC BY-SA 2.0

Tom Brady

Trump may have a contingent of secret service men, but he’s glad to have quarterback Tom Brady too. The New England Patriots’ quarterback has been friends with Trump for almost two decades when they first met at a Miss America Pageant in 2002. Brady still has his MAGA hat in his locker from 2015.
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Larry King

Television and radio host Larry King considers Donald Trump to be one of his oldest friends. In 2017, King went on record during an MSNBC interview to state that he and Trump used to go to the Super Bowl and have had numerous dinners in New York. He also says that the two of them went to see a Broadway show together.
Gage Skidmore / Creative Commons

Oprah Winfrey

President Trump may not be popular with a lot of women, but he’s a huge fan of Oprah Winfrey. In 1999, Trump showered Oprah with compliments. In 2015, he added he would win a presidential election if Oprah was his running mate. But then Trump Tweeted: “Hope Oprah runs so she can be exposed and defeated just like all of the others!” This was after she hinted she would run in 2020.
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Regis Philbin

Media personality Regis Philbin first met in 1983 and their friendship has grown stronger ever since. Philbin and Trump hit it off right away and their friendship blossomed from there. "We just became friends and we’ve been seeing each other ever since," Philbin told Newsday in a 2016 interview. He also said that he thought The Donald was all around “a great guy.”
Paparazzo Presents / CC BY-SA 3.0

Tony Bennett

Fans of American singer Tony Bennett may be surprised to learn that he and Trump are besties. Bennett and Trump have known each other for quite a long time, so it’s no surprise that the singer once told reporters that he would be doing something for the president at some point. It may be that he was suggesting he might perform for The Donald or speak in support of him.
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Don King

Don’t expect Donald Trump and boxing promoter Don King to come to blows anytime soon. The two of them are like two peas in a pod. If Don King were to pick up the phone right now and ask Trump for help with something, The Donald would likely stop what he was doing to lend his old friend a hand.
mborowick / CC BY 2.0

Sean Combs

Donald Trump once had nothing but rapper Sean Combs, aka P. Diddy’s utmost respect. In 2015, P. Diddy told the Washington Post “Donald Trump is a friend of mine, and he works very hard." But since Trump became president, the friendship seems to have gone sour. In fact, Diddy slammed Kanye for his willingness to meet with The Donald at the Oval Office in 2018.
Reckless Dream Photography / CC BY 2.0

Anna Wintour

Vogue editor Anna Wintour and the President are actually really tight in real life. Wintour not only attended Trump’s 2005 wedding, but she also offered Ivanka Trump a job at Vogue. But in 2019, Melania’s reps slammed Wintour for stating that Vogue only profiles women they believe in after excluding the First Lady from their list.
Myleskalus / CC BY-SA 4.0

Martha Stewart

It’s no secret that Martha Stewart and Trump have bonded over time. She once hosted a spinoff of “The Apprentice.” The two of them were such good friends that Trump recently considered pardoning Stewart for a 2004 charge of obstructing justice and lying about those Enron shares she sold. He claimed that she was treated harshly and unfairly. But before the presidential election Stewart had harsh things to say about Trump and claimed she was voting for Clinton. According to the Chicago Tribune after the election, Stewart said, “I sent my congratulations to the Trump family, and I think they have an opportunity — let's see how they do with it,”
David Shankbone / CC BY 3.0

Roseanne Barr

When Roseanne Barr’s sitcom “Roseanne” was revived by ABC, it became clear she was pro-Trump. The president even rang her up and congratulated Barr for her show’s amazing ratings. But she got fired from the series after she posted a pretty controversial tweet about a former Obama administration official on Twitter. Now, Barr can be seen on YouTube where she posts her thoughts about Trump and politics.
Leah Mark / CC BY-SA 2.0