Trump's Complicated History With Oprah, Explained
Over the years, former President Donald Trump and billionaire Oprah Winfrey have maintained a professional friendship, but now that Oprah has endorsed Vice President Kamala Harris for president in the 2024 election, it seems things have fully turned sour.
For more than two decades, Trump and his family made multiple appearances on Oprah's wildly successful daytime talk show, "The Oprah Winfrey Show." This, it seems, led Trump to develop a unique soft spot for Oprah.
"The Apprentice" host has repeatedly suggested that not only has Oprah visited Trump's Mar-A-Lago estate for some key lime pie, but that he was also a guest during the final week of her show. As benign as these claims appear, according to CNN, the latter has been repeatedly proven false. Yet, for Trump to continue to repeat this lie indicates his desire to still be a major part of Oprah's career.
Trump was friendly with Oprah until he ran for president
The relationship between Donald Trump and Oprah Winfrey dates back to the 1980s, with Trump often having nice things to say about Oprah. However, their relationship soured when he first ran for president in 2016. Oprah has never endorsed Trump in any of his campaigns, always opting for the Democratic candidate. This has led him to throw barbs at her, and according to Politico, Trump has suggested Oprah wouldn't be able hack it in her own presidential campaign.
Trump decided to take his woes to former Oprah mentee, Dr Phil McGraw. According to Newsweek, this is when Trump dove back into the falsehood he's been repeating for more than a decade now: that he was invited to appear on the final week of "The Oprah Winfrey Show." After the Dr. Phil interview, Oprah held a live-streamed rally for the Harris campaign, which Trump seems to have taken personally. On September 21, 2024, Trump bemoaned on his social media platform, Truth Social, "I couldn't help but think this isn't the real Oprah."
Whereas it is true that he and his family appeared on the final season of the show, their appearance was a few months prior to the final taping. Beyond this, Oprah famously hosted her farewell show solo, wanting to remind all her friends and fans "to understand the power they have to change their own lives."