The 2024 Democratic National Convention in Chicago, Illinois was unexpectedly graced by the appearance of Oprah Winfrey, who came to voice her support for Vice President Kamala Harris’ presidential bid. This received a mixed response, with a surge of applause and a wave of controversy.
Winfrey, a billionaire and television icon, delivered a fervent speech, advocating for decency, respect, and common sense. Her words, however, were met with opposition from the Trump campaign. In response, they dredged up an old letter of commendation Winfrey had once written to Donald Trump.
Throughout her speech, Winfrey implored Americans to prioritize their loyalty to the Constitution over any individual. She underscored the necessity of electing leaders who personify the nation’s core values, stating, “Decency and respect are on the ballot in 2024,” she proclaimed amid standing ovations, “And just plain common sense—common sense tells you that Kamala Harris and Tim Walz can give us decency and respect.”
Winfrey’s public endorsement sparked a heated debate. The Trump campaign’s “War Room” X account retaliated by unveiling a private letter that Winfrey had sent to Trump, 20 years ago, in January 2000. In this letter, responding to a snippet from Trump’s book “The America We Deserve,” Winfrey expressed her admiration for his leadership. She wrote, “Donald—I reviewed the book excerpt. I have to tell you, your comments made me a little weepy,” the letter read. “It’s one thing to try and live a life of integrity—still another to have people like yourself notice. Thank you.”
Adding fuel to the fire, the Trump campaign highlighted a line at the end of Winfrey’s letter: “Too bad we’re not running for office. What A TEAM!” This move, seen by many as an attempt to undercut Winfrey’s endorsement of Harris, brought to light her previous admiration for Trump.
Over the years, the relationship between Winfrey and Trump has evolved. In the same book containing the mentioned letter, Trump recalled how their rapport soured after he initiated his presidential campaign. He wrote, “Sadly, once I announced for President, she never spoke to me again.”
In addition to endorsing Harris, Winfrey’s speech at the DNC served as a critique of the prevailing political climate, with specific reference to controversial comments made by Trump’s running mate, Ohio Senator JD Vance, about “childless cat ladies.”
Given her influence and the historical “Oprah effect,” which has previously swayed public opinion, Winfrey’s endorsement is seen as significant. Her backing of Barack Obama in 2008, for instance, is often credited with significantly benefiting his Democratic primary campaign. Similarly, her endorsement of Harris is viewed as a potential rallying point for undecided voters and independents.
The strategic decision by the Trump campaign to publicize Winfrey’s old letter is an effort to depict her as inconsistent and call attention to her past praise for Trump. Nonetheless, the contrast between her words from 2000 and her 2024 speech is also indicative of the political and social changes that have occurred over the past two decades.
As the 2024 election nears, endorsements from influential personalities like Winfrey could markedly influence public opinion. It remains uncertain whether the resurfacing of a letter from 24 years ago will sway the electorate, but it’s evident that both campaigns are employing every possible strategy in their quest for the presidency.
