‘He has met his match’: TrumpNation author says White House has ‘lost the messaging’ over shutdown

Donald Trump biographer Tim O'Brien explained Trump's "strange" relationship with women while declaring he has "met his match" in Speaker Nancy Pelosi.

O'Brien authored the 2005 book TrumpNation: The Art of Being the Donald.

"What are we learning and seeing about Donald Trump that you learned and saw long ago in your reporting?" the host asked.

"Well, he is an affluent man who was born into wealth and he doesn't have an authentic connection to the struggles and the needs of average people," O'Brien explained.

"We saw that when Puerto Rico got hit by a hurricane," he noted. "It took the president a long time to go to a war zone. He didn't get out to California when the wildfires were burning and now he has shut down a government and the people who work for him are struggling and he doesn't have any empathy with what that struggle involves."

"And I think beyond the lack of empathy, there is also a lack of strategic sophistication -- they have lost the messaging," he observed. "Symbolically, now not only has Trump said as famously as he did in December, 'I'm willing to own the shutdown.' He is being painted publicly as someone who doesn't care about the human impact of the shutdown as well and that will live with him for a long time."

"What have we learned about how Trump is adjusting to Nancy Pelosi, with whom he shares politics and a generation in America?" Williams asked. "Has he met his match that he didn't see coming?"

"I think he's met his match," O'Brien answered. "Trump has had a very interesting and strange history with women. Attractive women or beautiful women he treats them like ornaments on his Christmas tree. And then he's had strong-minded women in his organization, they tend not to be women he is interested in romantically and he has varying levels of respect to them."

"I think in Nancy Pelosi, he has authentic respect," he added.

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