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The 1988 Oprah Winfrey interview with Donald Trump aired on April 25, 1988 (Season 3, Episode 5 of The Oprah Winfrey Show). At the time, Trump was a prominent New York real estate developer and celebrity, fresh off placing a high-profile full-page ad in major newspapers (like The New York Times) in 1987 criticizing U.S. foreign policy… She asked if he’d ever run for president. Trump replied: “Probably not.” But he added the famous caveat: “If it got so bad, I would never want to rule it out tota
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