Last Updated Mar 3, 2018 3:42 PM EST
President Trump will venture into hostile territory Saturday night at the annual Gridiron dinner, mingling with members of the mainstream media he loves to lash out against.
The white-tie gala is one of the city's longest-running traditions, and the kind of establishment event that Mr. Trump has so far shunned. But what is supposed to be a lighthearted bread-breaking between the president and press risks becoming a flashpoint if Trump, who has labeled reporters "fake news" and the "enemy of the American people," proves unable to poke fun at himself or take a lashing from the press.
"I think he is in a potentially strange spot where he either attacks the press in a way that works really well at a rally but just gets crickets in that room, or he has spent the past two years calling reporters 'fake news' and then suddenly admits it's just the act," said David Litt, a former speechwriter for President Barack Obama who helped write many of Obama's comedy speeches.
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https://www.cbsnews.com/news/trump-to-roast-and-be-roasted-at-rare-dinner-washington-media/