The Trump campaign responded to Oprah Winfrey’s speech at the Democratic National Convention Wednesday by resurfacing an admiring letter she once wrote to the man she’s now urging voters to reject.
In her surprise appearance in Chicago, the billionaire TV star encouraged fellow independents to join her in endorsing Vice President Kamala Harris’ campaign. “Decency and respect are on the ballot in 2024,” she said to rapturous applause. “And just plain common sense—common sense tells you that Kamala Harris and Tim Walz can give us decency and respect.”
Winfrey also encouraged voters to “choose loyalty to the Constitution over loyalty to any individual,” and invoked a Harris campaign slogan by adding: “Let us choose the sweet promise of tomorrow over the bitter return to yesterday… We’re not going back.”
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“Let us choose joy, because that’s the best of America,” Winfrey said in closing. “But more than anything else, let us choose freedom, why? Because that’s the best of America. We’re all Americans, and together let’s all choose Kamala Harris!”
The comments apparently touched a nerve in the Trump camp.
His campaign’s “War Room” X account shared a private handwritten letter Winfrey sent to Trump in January 2000. She penned the note in response to an excerpt Trump had sent her from his book The America We Deserve in which he wrote that she would be his “first choice for vice president.”
“Donald—I reviewed the book excerpt. I have to tell you, your comments made me a little weepy,” Winfrey’s letter reads. “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: “Too bad we’re not running for office. What A TEAM!”
Axios reported on the note last year when Trump included it in a book compiling 150 private letters. In the book, Letters to Trump, the former president wrote that he still regards Winfrey as “amazing,” but acknowledged the sentiment was not reciprocated. “Sadly, once I announced for President, she never spoke to me again,” Trump wrote.
In her speech Wednesday, Winfrey also took a shot at Trump’s actual pick for vice president, Ohio Sen. JD Vance, and his comments about childless cat ladies. Winfrey said that, when a house is on fire, Americans don’t ask about the homeowner’s race, religion, sexuality, or politics.
“We just try to do the best we can to save them,” Winfrey said. “And if the place happens to belong to a childless cat lady, well, we try to get that cat out too.”
