Actually I have, during his "Apprentice" days, back in the early part of this century.
I thought he was an amusing dolt then, (I enjoyed his line about how to become a millionaire, but I didn't realise it wasn't a joke) but now I know he's just a dolt.
Have you met him? I know he surrounds himself with grifters, conmen and misogynists, so that would figure.