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The government shutdown is now the longest in U.S. history, but President Donald Trump seems no closer to a deal to resolve it. Why does the “master deal maker”—as he sold himself on the campaign trail—seem at a loss in his first negotiation with a Democratic House?

On this week’s Radio Atlantic, the New York Times White House correspondent and “Trump whisperer” Maggie Haberman joins Alex Wagner to explain how Trump’s business career actually predicted his performance during the shutdown.

Listen to hear about how, after he became a celebrity in the 1980s, Trump wasn’t the greatest negotiator. He cut a terrible deal with the very man who authored The Art of the Deal and torpedoed what would have been the real-estate project of his career with a public spat.

Maggie and Alex discuss how the president’s tactics in New York real estate parallel and explain his shutdown politics.

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