However, the Republican appeared to lose the room as he repeatedly dug in with caustic swipes at Mrs Clinton, drawing rare boos at a charity event meant to raise money for impoverished children throughout New York.

"Hillary is so corrupt she got kicked off the Watergate Commission. How corrupt do you have to be to get kicked off the Watergate Commission? Pretty corrupt," he said to loud jeers and at least one call demanding he get off the stage.

He then rattled off his standard attack lines, setting aside humour as he talked about the material contained in hacked Clinton campaign emails.

"Hillary believes that it's vital to deceive the people by having one public policy and a totally different policy in private," he said to growing jeers. "Here she is tonight, in public, pretending not to hate Catholics."