Here's What Oprah Winfrey Said After Donald Trump Asked Her to Be His Running Mate in 2000

Once, former President Donald Trump released a book containing private letters from prominent figures, including a letter from Oprah Winfrey dating back to 2000. This exchange shed light on an intriguing moment in their relationship, flaunting a glimpse into the dynamics between two influential personalities. Winfrey, a famous media personality and philanthropist, wrote a letter to Trump in 2000, expressing camaraderie in a playful spirit after he pondered over her being his potential VP back then. She remarked, "Too bad we're not running for office. What a TEAM!"

During an interview on CBS Mornings, Winfrey recalled the letter and its inclusion in Trump’s book. She reminisced, "I think he'd written a book and said that he wanted me to be his running mate ... if he decided to run. And when I heard that this letter is now going to be a part of a book, I thought, 'Oh, wasn't that nice of me to write a note.' That's what I thought, because I'm always like, 'Oh, I should write a note. The person did this, or I should write a note,'" she said. "So I'm really happy that I wrote a note," as reported by CBS News.

Despite the playful banter in the letter and Trump’s expressed desire to have Winfrey as his running mate, Winfrey clarified that she would not consider such a partnership anytime soon. She exclaimed, "I might have thought it back then. I might have thought it 23 years ago. I'm not thinking it today."

As per The New York Post, this literary endeavor from Trump not only features what Winfrey told him but also includes correspondence from a diverse array of figures, including former President Bill Clinton, Princess Diana, Richard Nixon, Kim Jong Un, and others. The book offers readers a unique glimpse into the private interactions between Trump and prominent individuals spanning decades.

Circling back, Trump’s inclination towards Winfrey is evident from past interactions and statements. Despite their differing backgrounds and ideologies, Trump has lauded Winfrey before. In an interview with Larry King about a potential presidential run as an independent in 1999, Trump shared, “Oprah. I love Oprah. Oprah would always be my first choice. If she’d do it, she’d be fantastic. I mean, she’s popular, she’s brilliant, she’s a wonderful woman. I mean, if she would ever do it. I don’t know that she would ever do it. She’s got, you know. She would be sort of like me,” as reported by Time.

In a tweet from his pre-presidential era, Trump expressed, “Oprah will end up doing just fine with her network--she knows how to win. @Oprah” Trump also shared his admiration for Winfrey in an interview with ABC News, where he remarked, “I think Oprah would be great. I’d love to have Oprah. I think we’d win easily, actually.” Trump reiterated this sentiment in subsequent interviews, highlighting Winfrey's popularity, brilliance, and appeal as a potential political ally. Alas, it is not to be, at least as things stand now.

Editor's note: This article was originally published on April 7, 2024. It has since been updated.