In 2000, Donald Trump appeared in a comedic sketch alongside Rudy Giuliani, who was dressed in drag as part of a New York City political roast. In the bit, Giuliani, portraying a wealthy socialite version of himself, encounters Trump, and the interaction becomes playfully flirtatious. | History In Pictures
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In 2000, Donald Trump appeared in a comedic sketch alongside Rudy G…
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Rudy Giuliani wore a dress and got felt up by Donald J. Trump in a transphobic sketch ripped straight from your nightmares. | New York Magazine
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