The unexpected arrival of Oprah Winfrey at the Democratic National Convention in Chicago, Illinois this week sparked both applause and debates. The television icon openly backed Vice President Kamala Harris’ bid for the presidency.
Winfrey delivered a fervent speech calling for decency, respect, and common sense. However, this did not sit well with the Trump campaign. They promptly reacted by bringing to light a very old letter of admiration Winfrey once wrote to Donald Trump.
Renowned for her television success and wealth, Winfrey captured the convention’s attention with her endorsement. She urged Americans to prioritize loyalty to the Constitution over loyalty to any individual. She stressed the need to elect leaders that reflect 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 soon stirred up controversy. A private, handwritten letter from Winfrey to Trump dating back to January 2000 was shared by the Trump campaign’s “War Room” X account. The letter, which was a response to a passage from Trump’s book “The America We Deserve,” expressed her admiration 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,” and continued, “It’s one thing to try and live a life of integrity—still another to have people like yourself notice. Thank you.”
In the letter, Winfrey added a line that the Trump campaign seized on: “Too bad we’re not running for office. What A TEAM!” The re-emergence of this letter was seen by many as an attempt by the Trump campaign to question Winfrey’s endorsement of Harris by highlighting her previous praise for Trump.
The relationship between Winfrey and Trump has evidently evolved over time. In the same book that carried the letter, Trump reflected on their relationship that declined after his presidential campaign announcement. Trump noted, “Sadly, once I announced for President, she never spoke to me again.”
The speech by Winfrey at the DNC encompassed more than just her endorsement of Harris. It also included a pointed critique of the prevailing political climate, particularly targeting controversial remarks made by Trump’s running mate, Ohio Senator JD Vance, about “childless cat ladies,” which had garnered significant criticism.
The endorsement by Winfrey carries weight given her influence and the well-known “Oprah effect” that has influenced public opinion in the past. Her backing of Barack Obama in 2008 is often attributed with providing a significant lift to his campaign during the Democratic primary. Her endorsement of Harris is seen as a significant advantage for the campaign, potentially rallying undecided voters and independents.
The strategic decision by the Trump campaign to reveal the old letter aimed to depict Winfrey as inconsistent and underline her earlier praise for Trump. However, the contrast between Winfrey’s words in 2000 and her 2024 message also illustrates the broader political and social changes over the past 24 years.
The reaction from the Trump campaign, while spotlighting past connections, also highlights the deepening political divides in the country. As the 2024 election draws closer, endorsements from prominent individuals like Winfrey could be key in swaying public opinion. The impact of revealing a letter from 24 years ago on the voting public remains to be seen, but it’s clear that both campaigns are leaving no stone unturned in their race for the nation’s highest office.
