Researcher and biographer Michael D’Antonio walked through the decades of bungled “deals,” that President Donald Trump had while negotiating in New York. To make matters worse, he thinks this might be the first time Trump has had to go up against a powerful woman.

“There’s a huge difference between the deals that Donald Trump used to be involved with and deals involving national security and federal employees and hundreds of thousands of people,” remarked CNN reporter and sometimes host Dana Bash.

D’Antonio agreed, noting that Trump came up with this “walk away” negotiation tactic, but it hasn’t actually worked in the past.

“I think in his past, the president actually lost a billion dollar deal on the Upper West Side when he made Ed Koch angry at him,” the biographer told Anderson Cooper Wednesday. “And the mayor wasn’t going to go along with this television city project that had real potential. He did this also with the United States Football League where all the other owners wound up being really angry. Because he pushed something beyond what was constructive.”

When it came to Trump and Speaker Nancy Pelosi, however, D’Antonio thinks Trump is in over his head.

“As I’ve been watching this, I’ve been thinking about the fact that this is a man who has been having tantrums for 72 years,” he continued. “You know, and what Nancy Pelosi is doing is what a good mother does. She doesn’t give in to the kid having a tantrum. Chuck Schumer may not have that impulse because maybe he wasn’t as active a parent as Nancy Pelosi has been. But the last thing you do is give a who’s having a tantrum what he wants. I think this is perplexing the president. I think he’s met his match in Mrs. Pelosi.”

Indeed, Pelosi is the mother to five children and grandmother. Dealing with children isn’t a foreign concept to her.

“It doesn’t matter what people are saying to him,” Dana Bash, CNN’s chief congressional correspondent said. “It’s what he believes and he is firmly confident that this is the right thing to do for him politically. And that’s what a Republican senator who was in the private meeting with him told me today. It’s not that he is necessarily arguing that it’s the right thing to do for national security although he has said that. That he is in a good place politically and that is what is really rankling a lot of people and helping to entrench the Democrats because they see believes this is a political interrogative for him.”

D’Antonio also noted that this is the first time that he can think of where Trump has been forced to go up against a powerful woman and it’s likely difficult for him. He said that people should probably be looking more to Trump’s emotions and personality rather than strategy.