Oprah and Trump used to love each other. What went wrong?

One of the striking things about Oprah Winfrey’s recent interview with Kamala Harris was the fact that two decades ago, Winfrey was quite close to Harris’ opposite number. While the RNC put out a statement criticizing Kamala Harris for campaigning with Oprah and said: “…campaigning in Michigan with an out-of-touch celebrity, further confirming that the Democrat party is not the party of hardworking Americans – it is the party of elitists”
Oprah Winfrey faced significant backlash from MAGA supporters after her surprise appearance at the Democratic National Convention, where she endorsed Kamala Harris and indirectly criticized Donald Trump.Although she did not mention Trump by name, her comments were sharp. She emphasized the importance of "decency, respect, and common sense" in the 2024 election, contrasting Harris with Trump’s running mate, JD Vance, who had made a controversial remark about "childless cat ladies."

Following Oprah’s appearance at the RNC, old videos and a personal letter she wrote to Trump in January 2000 resurfaced. In the letter, which was in response to an excerpt from Trump’s book , Oprah expressed admiration for him, calling his words "weepy" and praising his integrity. Trump had also stated in the past that Oprah was his first choice for vice president, and Oprah playfully responded, "Too bad we're not running for office. What a team!"

This letter was later featured in Trump’s book , where he acknowledged that Oprah stopped communicating with him after he announced his presidential run. Additionally, a clip of Trump on Oprah’s show from years ago began circulating among Republicans, who claimed she once admired him but has since "changed her tune."
Oprah’s political endorsements have been consistent over the years. She first endorsed Barack Obama in 2008, supported Hillary Clinton in 2016, backed Joe Biden in 2020, and endorsed Jon Fetterman in 2022. However, her appearance at the Democratic National Convention marked her first official role at a political convention, where she expressed strong support for Kamala Harris and Tim Walz.