Donald Trump Teases a President Bid During a 1988 Oprah Show | The Oprah Winfrey Show | OWN

-For more The Oprah Winfrey Show visit Original airdate: April 25, 1988 Donald Trump is perhaps best known for the money he’s made (and lost) in real estate, his less-than-humble demeanor and his hit reality TV show, ’The Apprentice.’ In recent years, the business tycoon has also been chasing the dream of holding the highest office in the land. Although many people know he has been eyeing the Oval Office for a couple of election cycles, you may be surprised to learn just how far back