The NBC News national affairs analyst explained on Tuesday how the 2020 Democratic Party nominee can exploit President Donald Trump's "psychological weakness" during televised debates.
John Heilemann was interviewed by Lawrence O'Donnell on MSNBC's "The Last Word."
The host played a clip of how Trump presents himself to voters.
"I’m really rich. I’ll show you that in a second. And, by the way, I’m not even saying that in a brag — that’s the kind of mindset, that’s the kind of thinking you need for this country," Trump said.
"What happens to that line, John?" O'Donnell asked.
"I imagine he’ll keep saying it," Heilemann replied.
"I mean, he is still rich," O'Donnell noted. "Let’s remember that part."
"Richer than many people," Heilemann said. "And the truth has never stopped Donald Trump from what his claims might be, so I imagine he’ll keep saying that until the day he dies, regardless of whether we see his taxes or not."
"If you think about the three points you made at the beginning, right, one, he’s not that rich, two, he doesn’t pay very many taxes, three, he was reliant on his father, right? They’re revealing in different ways," he explained.
Heilemann said the fact Trump wasn't that rich was a political liability, that he's a fraud. The issue of lack of taxes showed Trump "may also be a crook" and represented a legal liability.
But the third, that he was reliant on his father, represented a psychological liability.
"Hillary Clinton’s people picked up on it very quickly," Heilemann reminded. "You remember in the first debate in 2016, that a sore toe for Donald Trump would be to raise his father and he needed his father to get any kind of financial success. They hit him on it early into the debate, it was the moment about a half an hour into the first debate when he lost it because she had drilled into this phycological tender spot for him."
"Any Democrat thinking about running against Donald Trump in 2020, if you’re thinking about a psychological profile -- in addition to a legal and political profile -- on how you run against him, the relationship with the father and the psychological weakness it exposes is one you can hammer again and again in a much more devastating way than Clinton tried to do in 2016," Heilemann concluded.