12 surprising celebrities Donald Trump has been friends with over the years

As a billionaire reality TV star and real estate mogul in New York, a lot of people have tried to get into Donald Trump’s inner circle over the years.

From politics to business and to Hollywood, it’s not surprising that Trump has had friends in almost every line of work.

But here are 12 people you may not have known Trump befriended:

Trump took a liking to Mike Tyson when he starting hosting some of the boxer’s biggest matches at Trump Plaza in Atlantic City. When Tyson was convicted of rape in 1992, Trump defended the boxer, calling the verdict “a travesty.”

Source: CNN

Shortly after the 2016 election, Trump met with rapper Kanye West at Trump Tower in New York. “We’ve been friends for a long time,” Trump said, adding that the two discussed “life” during their meeting.

Trump meets with Kanye at Trump Tower in December 2016, shortly after winning the election.
REUTERS/Andrew Kelly

Source: Business Insider

Journalist Barbara Walters has been friends with Trump on and off for years. After having a bit of a falling out in 2007 after she defended Rosie O’Donnell’s criticisms of Trump, Walters “rekindled” their friendship two years later, saying “I’ve missed you.”

Barbara Walters attends the wedding of Trump’s daughter, Ivanka, and her husband, Jared.
Brian Marcus/Getty

Source: The Today Show

Trump has long admired Oprah Winfrey, the much-beloved media mogul and self-made billionaire. In 1999, Trump said he “loves” Oprah and called her a “popular, brilliant … wonderful woman.” In 2015, Trump said he would win the presidency “easily” if Oprah were his running mate.

Donald Trump teases a presidential bid during a 1988 appearance on “The Oprah Winfrey Show.”

Source: Business Insider

Yet their relationship deteriorated over the years. In January, she delivered a powerful speech excoriating him at the Golden Globe awards — prompting many to speculate at 2020 presidential bid. In February, Trump tweeted, “Hope Oprah runs so she can be exposed and defeated just like all of the others!”

Oprah speaks at the 2018 Golden Globe Awards.
Paul Drinkwater/NBCUniversal via Getty Images

Sources: Business Insider, Twitter

Longtime broadcaster Larry King has personally known Trump for decades, calling him one of his “oldest, dearest friends.” During an interview on MSNBC in 2017, King recalled going to the Super Bowl with Trump, attending a Broadway show, and having many dinners in New York together.

Source: MSNBC

TV personality Regis Philbin met Trump back in 1983. “We just became friends and we’ve been seeing each other ever since,” Philbin said in a 2016 interview with Newsday. “I think he’s a great guy.”

Source: Newsday

Entrepreneur Russell Simmons has been friends with Trump for decades, but Trump’s presidency has strained their relationship. “You’re smarter and certainly more loving then [sic] you let on,” Simmons said to Trump in an open letter in December 2015. “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.”

Business Insider / Will Wei
Source: Global Grind

Fellow New Yorker and singer Tony Bennett has been close to Trump for a long time and considers himself a friend. Last year, Bennett told reporters: “Sooner or later, I’ll probably be doing something for him,” perhaps hinting that he would perform for the president.

Tony Bennett at Grammys 2018
Dimitrios Kambouris/Getty Images for NARAS

Source: Billboard

Controversial boxing promoter Don King told Politico last year that he is still a good friend of Trump’s and can easily get him on the phone to talk to him about urgent matters. The two dined together at the president’s Mar-a-Lago resort last week.

Sources: Politico, Washington Post

Rapper P. Diddy, whose real name is Sean Combs, told the Washington Post in 2015 that he “always liked Donald’s style,” admired his work ethic, and that he and Trump are friends.

REUTERS/Shannon Stapleton

Source: Washington Post

Anna Wintour, the legendary editor of Vogue, has been in Trump’s orbit for years. She attended Trump’s wedding in 2005, offered Ivanka Trump a job at her magazine, and reportedly met with Trump shortly after the 2016 election.

Anna Wintour and Donald Trump, pictured together in 2005.
Jeff Zelevansky-Pool/Getty Images

Source: Slate

New England Patriots’ quarterback Tom Brady and Trump go back more than a decade. When their relationship drew scrutiny ahead of the 2016 election, Brady described Trump as “a good friend” who has “always been so supportive of me.”

Source: CBS Sports