Oprah Winfrey and Donald Trump were once known to share a friendship. However, after Winfrey openly criticized the former president during the Democratic National Convention, their relationship has clearly shifted. Winfrey, an emblematic figure in the media landscape, was reminded of her previously expressed hope that Trump might run for president.
Her unexpected appearance in Chicago exemplified how celebrities have increasingly backed the candidacy of Vice President Kamala Harris, who is expected to be nominated officially by her party soon. During her speech, Winfrey emphasized her break from Trump, stating, “We know all the old tricks and tropes that are designed to distract us from what actually matters. 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.”
(VOTE: Are You Supporting TRUMP Or KAMALA In November?)
Not too long ago, Winfrey, aged 70, expressed an interest in possibly joining Trump on a presidential ticket. Shortly after her recent speech, a resurfaced 2,000-word letter from Winfrey to Trump revealed her earlier support where she mused about leading the nation together. “Too bad we’re not running for office,” she once remarked. This letter, dated June 11, 2000, was penned after she reviewed Trump’s book and shared how it moved her profoundly. Recently, in a more candid interview, Winfrey reflected on her past thoughts about Trump: “I might have thought it back then,” she admitted, “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
Her earlier supportive message contrasts sharply with the critical stance she took on stage when announcing her endorsement for the Harris-Walz ticket. Winfrey cautioned her audience about the gravity of the November election, stating, “When a house is on fire, we don’t ask about the homeowners’ race or religion. We don’t wonder who their partner is or how they voted. We just try to do the best we can to save them. And if the place happens to belong to a childless cat lady, 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.”
Reiterating her core message, Winfrey asserted that “values and character matter” most in this election. “Most of all,” she noted, “in leadership and in life, you know this to be true: decency and respect are on the ballot in 2024. And just plain common sense should prevail over loyalty to any individual.”
In response, President Trump has refrained from directly attacking Winfrey, instead releasing a pointed 30-second advertisement criticizing Harris regarding her previous positions on criminal justice reform as California’s attorney general. While Minnesota Gov. Tim Walz addressed the audience, Trump shared this ad on Truth Social, which includes claims that Harris endorsed “radical ideas” that funded the release of violent criminals. Notable in the ad is the case of Shawn Michael Tillman, a repeat offender linked to homicide following his release. The GOP is clearly strategizing against Harris and Walz, highlighting numerous subjects to leverage, from Walz’s alleged “stolen valor” military service to Harris’s communication style and her reluctance to hold press conferences.
(FREE RED HAT: “Impeached. Arrested. Convicted. Shot. Still Standing”)
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