Old Pics Of Donald Trump & Oprah Winfrey Highlight How Far He's Fallen From Grace

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Before he became the President of the United States, Donald Trump was best known for being a TV star. His reality competition series, "The Apprentice," was huge, with 21 million people tuning in for the first season. But even before that, Trump was a popular guest on talk shows. The controversial New York real estate mogul would regularly appear on a variety of shows, from Howard Stern's morning radio program to Oprah Winfrey's popular daytime talk show. And while it may not have been her intention, it seems like Winfrey fed into Trump's future political aspirations with a polite comment. In his 2023 book, "Letters to Trump," the president published private correspondence he received from a number of celebrities and politicians. In a letter Winfrey sent to Trump in 2000, she wrote (via the Daily Mail): "Too bad we're not running for office. What a team!"

Winfrey spoke about the letter on CBS News, explaining that she sent the message in response to Trump floating the idea of her being his running mate in his book, "The America We Deserve," and admitted to her decades-long friend Gayle King, that while she may have believed that Trump would have been a good presidential candidate in 2000, she didn't feel that way in 2023. According to Trump, the two used to be very close, and Oprah even visited Mar-a-Lago for some key lime pie.

Oprah Winfrey isn't the only celebrity who used to be friends with Donald Trump. While there are still a few Hollywood A-listers Trump can call on these days, there are plenty that have distanced themselves from the president since he first ran in 2016. Def Jam co-founder Russell Simmons was so close to Trump that Simmons told the New York Daily News that he was there the night Trump met Melania and that he was a regular guest at Mar-a-Lago. The friendship came to a crashing halt when Trump announced his candidacy for the presidency in 2015. While on Fox Business, Simmons said that a Trump presidency "would be a terrible thing for America," before suggesting that Kim Kardashian would be a better choice for the job of Commander-in-Chief. After that interview, Trump called Simmons, but the record producer wouldn't take the call.

Anna Wintour, the fashion icon and former editor-in-chief of Vogue, went on "The Late Late Show with James Corden" in 2017 and made it clear that Trump and his family would no longer be welcome at the annual Met Gala. Before that, Wintour and Trump were close; she not only attended Donald and Melania's 2005 wedding, but she also put Melania on the cover of the February 2005 issue of Vogue. And while Wintour supported Hillary Clinton in the 2016 election, she attempted to be cordial to Trump after the election, apologizing for comments she made about him in 2016. But, as her appearance on Corden's show demonstrates, her attempts to keep a friendly relationship with Trump didn't last long.