Oprah Winfrey’s surprise appearance at the 2024 Democratic National Convention in Chicago, Illinois this week stirred both applause and controversy as she threw her support behind Vice President Kamala Harris’ presidential campaign.
Winfrey’s speech, marked by passionate calls for decency, respect, and common sense, didn’t sit well with the Trump campaign, which quickly responded by digging into the past to resurface an old letter of admiration she once penned to Donald Trump.
Winfrey, a television icon and billionaire, captivated the convention audience with her endorsement, calling on Americans to “choose loyalty to the Constitution over loyalty to any individual.” Her speech emphasized the importance of selecting leaders who embody the values that define the nation. “Decency and respect are on the ballot in 2024,” she declared 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.”
This public endorsement, however, quickly became a point of contention. The Trump campaign’s “War Room” X account fired back by sharing a private, handwritten letter Winfrey had sent to Trump in January 2000. The letter, written in response to an excerpt from Trump’s book “The America We Deserve,” expressed her admiration for his leadership qualities. “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.”
At the bottom of the letter, Winfrey added a line that the Trump campaign was quick to highlight: “Too bad we’re not running for office. What A TEAM!.” This resurfacing of the letter was seen by many as an attempt by the Trump campaign to undermine Winfrey’s endorsement of Harris by showcasing her past admiration for Trump.
The relationship between Winfrey and Trump has clearly shifted over the years. In the same book where Trump published the letter, he reflected on how their connection deteriorated after he announced his presidential campaign. Trump wrote, “Sadly, once I announced for President, she never spoke to me again.”
Winfrey’s speech at the DNC wasn’t just about endorsing Harris; it was also a sharp critique of the current political climate, particularly targeting Trump’s running mate, Ohio Senator JD Vance. Winfrey didn’t hold back as she addressed Vance’s controversial comments about “childless cat ladies,” a remark that had drawn significant backlash.
Winfrey’s endorsement is considered significant, especially given her influence and the so-called “Oprah effect,” which has swayed public opinion in the past. Her support for Barack Obama in 2008 is often credited with providing a substantial boost to his campaign during the Democratic primary. This time, her endorsement of Harris is seen as a major gain for the campaign, potentially rallying undecided voters and independents.
The Trump campaign’s decision to publicize the old letter was a strategic move, aiming to portray Winfrey as inconsistent and highlight her previous praise for Trump. However, the contrast between Winfrey’s words in 2000 and her message in 2024 also reflects the broader political and social shifts that have taken place over the past two decades.
The Trump campaign’s response, while highlighting past connections, also underscores the deepening political divides in the country. As the 2024 election approaches, endorsements from influential figures like Winfrey could play a pivotal role in shaping public opinion. Whether the resurfacing of a 24-year-old letter will have any impact on the electorate remains to be seen, but it is clear that both campaigns are pulling out all the stops as they vie for the highest office in the land.
