Resurfaced Letter To Trump EXPOSES Oprah, Pours Cold Water On DNC Speech

Oprah Winfrey and Donald Trump were once close friends. After ripping the former president at the Democratic National Convention on Wednesday night, Winfrey was quickly reminded of how much she publicly loved the idea of him running the country someday.

The iconic talk show host’s surprise appearance in Chicago underscored how celebrities and Hollywood generally have flocked to the insurgent candidacy of Vice President Kamala Harris, who is set to be officially nominated by her party on Thursday evening. In her remarks, Winfrey signaled that she has come to a clean break with Trump. “We know all the old tricks and tropes that are designed to distract us from what actually matters,” Winfrey told the crowd at the United Center. “But we are beyond ridiculous tweets and lies and foolery. These are complicated times, people, and they require adult conversation. And I welcome those conversations because civilized debate is vital to democracy, and it is the best of America.”

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But it wasn’t so long ago that Winfrey, 70, wished to join Trump on a presidential ticket someday. Shortly after her speech, the Trump campaign posted a 2,000-word letter where she welcomed the opportunity to lead the country with him. “Too bad we’re not running for office,” Winfrey wrote, according to Fox News. “What a team!” The letter is dated June 11th, 2000, and came after Winfrey reviewed the latest copy of Trump’s book which she said made her “a little weepy” at times. During an interview last year, the daytime host reneged on her bonhomie with the former president. “I might have thought it back then,” Winfrey said in an interview at the time. “I might have thought it 23 years ago.”

Oprah's letter to President Trump: pic.twitter.com/QY1kYifPJS

— Trump War Room (@TrumpWarRoom) August 22, 2024

The kind note was a nice-and-day difference from the caustic tone Winfrey struck on stage as she announced her support for the Harris-Walz ticket and reminded Democrats of what’s at stake in the November election. “When a house is on fire, we don’t ask about the homeowners’ race or religion,” Winfrey said. “We don’t wonder who their partner is or how they voted no. We just try to do the best we can to save them. And if the place happens to belong to a childless cat lady. Well, we try to get that cat out too. Cause we are a country of people who work hard for the money. We wish our brothers and sisters well. And we pray for peace.”

This time around, Winfrey insisted to the crowd that she was “telling the truth” when she claimed that “values and character matter” most in this election. “Most of all,” Winfrey said, “in leadership and in life, you know, this is true, that decency and respect are on the ballot in 2024. And, and just plain common sense over loyalty to any individual.”

So far, President Trump has refrained from hitting back at his onetime celebrity friend, instead releasing a blistering 30-second ad targeting Harris’s support for bailing violent criminals out of jail while serving as California’s attorney general. As Minnesota Gov. Tim Walz took the stage Wednesday night, Trump posted the video on Truth Social which claims Harris promoted “radical ideas…. [to] raise money to fund the release of violent criminals” while California attorney general. The ad highlights the release of Shawn Michael Tillman, a repeat felon who was released and later charged with murder. The GOP continues to search for its most effective lines of attack against Harris and Walz and enjoys a wealth of subjects to draw on: claims about Walz’s “stolen valor” military service and his wife’s false statements about using IVF to Harris’s clunky deliveries and reticence to speak with the press.

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