Rudy Giuliani in Drag Smooching Donald Trump (Video) 1 discussions Yes, it's former NYC mayor Rody Giuliani in drag having his "breasts" shamelessly violated by "Apprentice" tycoon Donald Trump. Clip from new doc GIULIANI TIME, by Kevin Keating, now available on DVD .. Tags: giulianitime giuliani trump newyorkcity rudygiuliani donaldtrump 2008