Television personality Oprah Winfrey made an unexpected appearance at the 2024 Democratic National Convention in Chicago, Illinois, last week, where she publicly endorsed Vice President Kamala Harris’ presidential campaign. The move sparked both cheers and controversy.
Winfrey’s words, filled with fervent appeals for decency, respect, and logic, was met with disapproval from the Trump campaign. They promptly reacted by bringing back to the surface an old letter Winfrey had once written to Donald Trump, expressing her admiration.
The billionaire and television icon mesmerized the convention audience with her endorsement. She urged Americans to “choose loyalty to the Constitution over loyalty to any individual.” Winfrey stressed the election of leaders who represent the nation’s core values. “Decency and respect are on the ballot in 2024,” she proclaimed to a standing ovation, “And just plain common sense—common sense tells you that Kamala Harris and Tim Walz can give us decency and respect.”
However, this public endorsement promptly turned into a point of dispute. The Trump campaign’s “War Room” X account retaliated by unveiling a private, handwritten letter Winfrey had sent to Trump in January 2000. This letter, a response to an extract from Trump’s book “The America We Deserve,” demonstrated her respect for his leadership qualities. The letter read, “Donald—I reviewed the book excerpt. I have to tell you, your comments made me a little weepy. It’s one thing to try and live a life of integrity—still another to have people like yourself notice. Thank you.”
Winfrey’s concluding line in the letter, “Too bad we’re not running for office. What A TEAM!,” was promptly highlighted by the Trump campaign. They disclosed the letter in a bid to weaken Winfrey’s endorsement of Harris by showcasing her previous appreciation for Trump.
The bond between Winfrey and Trump has clearly changed over time. In the same book where Trump published the letter, he pondered over their deteriorating relationship after his presidential campaign announcement. Trump noted, “Sadly, once I announced for President, she never spoke to me again.”
Winfrey’s DNC speech didn’t solely serve to endorse Harris; it was also a pointed critique of the current political environment, specifically aimed at Trump’s running mate, Ohio Senator JD Vance. Winfrey openly addressed Vance’s controversial remarks about “childless cat ladies,” which has drawn significant backlash.
Winfrey’s endorsement holds considerable weight, particularly due to her influence and the so-called “Oprah effect,” which has influenced public opinion previously. Her 2008 support for Barack Obama is commonly credited with significantly boosting his campaign during the Democratic primary. Her endorsement of Harris is now viewed as a crucial advantage for the campaign, potentially rallying undecided voters and independents.
The decision by the Trump campaign to publicize the old letter was a calculated move, aiming to depict Winfrey as inconsistent and underline her past praise for Trump. However, the contrast between Winfrey’s 2000 expressions and her 2024 message also mirrors the wider political and social shifts over the last two decades.
While the Trump campaign’s response brings past connections to light, it also underlines the growing political divides in the country. As the 2024 election nears, endorsements from influential figures like Winfrey could play a crucial role in molding public opinion. The effect of a 24-year-old letter resurfacing on the electorate is yet to be determined, but it’s clear that both campaigns are leaving no stone unturned in their pursuit of the nation’s highest office.