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 his presidential aspirations reach. Watch as Donald, in a 1988 appearance on ‘The Oprah Winfrey Show’, shares his thoughts on running for office.