The frontrunner for the Republican presidential nomination, who has made a string of incendiary comments on the campaign trail, said Clinton got "schlonged" by Barack Obama.
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Trump laid into a number of his perceived enemies from the media to his rivals in a speech to supporters in Grand Rapids, Michigan on Monday night.
But he reserved his most stinging - and vulgar - remarks for Clinton, the clear frontrunner for the Democratic nomination for the White House in 2016.
"Even a race to Obama, she was gonna beat Obama," he said, referring to the 2008 presidential race, a giant United States flag draped on the wall behind him.
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"I don't know who would be worse, I don't know, how does it get worse? But she was going to beat - she was favored to win - and she got schlonged, she lost, I mean she lost," he said, turning a vulgar noun into a verb.
With a partisan crowd cheering him on, the billionaire real-estate tycoon also took issue with Clinton disappearing during Saturday's televised Democratic debate to go to the bathroom.
"I know where she went, it's disgusting, I don't want to talk about it," Trump said. "No, it's too disgusting. Don't say it, it's disgusting, let's not talk, we want to be very, very straight up."
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Trump, 69, also once again took aim at the press, describing them as "lying, disgusting people."
"I hate some of these people, but I'd never kill them," he added, before appearing to reconsider: "Umm, no, I would never do that."
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