Here's a bit on Trump weakness:
At only three points during the primary campaign did Trump look less than fully in command while on camera. His expression is the crucial part, not simply because images determine public impressions of most debates but also because of the nature of Trump’s dominance politics. For him to look taken aback, he must have registered internally that someone had gotten the better of him. His obvious falsehoods, from “Build a wall” on down, plainly don’t register with him as false while he’s saying them. It is significant that his face and carriage signaledI’m being owned at three moments during the primaries, only one of them during a formal debate.
The first was in late March, at a town hall in Wisconsin where he appeared alone onstage with Chris Matthews of MSNBC. Matthews asked him about his position on abortion, and Trump said, as if to dismiss the question, “I’ve been pro-life.” Matthews asked and asked again what exactly that meant. If abortion should become illegal, then who exactly would be breaking the law? And if the woman seeking an abortion is the criminal, what exactly should her punishment be? The structure of the primary debates had kept any of the candidates or moderators from drilling in this way. Thus almost never in the debates did Trump’s face go through the changes it did while he was onstage with Matthews, as he recognized that he was talking himself into a trap. The trap was coming right out and endorsing, as Trump found himself doing, the implicit but rarely stated logic of a strict pro-life view: that women who seek abortions should be subject to criminal penalties. (Later the campaign released a statement retracting that view, and saying that any criminal penalties should apply to the person performing an abortion, not the woman it was being performed on.)
The second was in an encounter with Megyn Kelly of Fox, but not the famous showdown of the very first debate, which she led off by asking why he had referred to women as “fat pigs” and “slobs.” (This was the basis for his later complaint that she had “blood coming out of her wherever.”) Instead it came nine months later, in May, during the debut of Kelly’s prime-time interview show on the Fox broadcast network, which has a vastly larger audience than the cable-based Fox News. The interview as a whole was generally panned as being too chummy and smarmy. But at one point Kelly asked Trump to explain the personally insulting tweets about her that he had written himself or that others had written and he had retweeted. He tried to laugh it off—“You’d be amazed at the things I don’t retweet”—but she did not laugh back.
She interjected, “ ‘Bimbo’?”
He replied, “Did I say that?”
“Many times,” Kelly said, staring right at him. Eventually Trump broke and said, “Okay, excuse me!” as a joke. She then switched, after a beat, to a laugh herself, but he didn’t look in control.
The final case was the only one to occur on a debate stage, and again involved a showdown with an unamused woman. This debate, in September at the Reagan library, was the first one in which Carly Fiorina joined Trump, Bush, Ben Carson, and others for the main event, rather than being consigned to the undercard. Moderator Jake Tapper asked Fiorina to respond to Trump’s saying about her, in aRolling Stone interview, “Look at that face. Would anyone vote for that?” Fiorina memorably said, “I think women across the country heard very clearly what Mr. Trump said.” Trump, at a loss, made things worse by saying, “I think she’s got a beautiful face! She’s a beautiful woman.” The split screen showed Fiorina turned away from Trump but looking daggers. Trump was saved as CNN cut to a commercial break.
Here was my favorite part of the article, on how Hillary should debate Trump:
Instead she could mock him on his other point of greatest sensitivity: that he may be a fake billionaire and phony business success. From history’s perspective, the most damaging moment for Trump from the Democratic convention was when Khizr Khan spoke about the death of his son, Captain Humayun Khan. For Trump himself, I would imagine it was the moment when Michael Bloomberg, unquestionably richer than he is, said, “I’m a New Yorker, and New Yorkers know a con when we see one.” When Comedy Central hosted a roast of Trump five years ago, he didn’t seem to object to jokes about his hair, about his weight, even about his lecherous remarks regarding his daughter Ivanka. The one subject he nixed, according to Aaron Lee, a writer for the roast, was “any joke that suggests Trump is not actually as wealthy as he claims to be.” So this is a scab Hillary Clinton should deftly pick.
Obviously, I've already started and did it before reading this. I say if you belittle his wealth, he has no choice but to brag about it. His pride won't allow him to do otherwise.
While Trump has lied about a great many things without serious repercussions, the revelation that his net worth is not what it appears could be extraordinarily damaging. His tax returns could also reveal that he keeps money in offshore bank accounts, or that he pays an insultingly low tax rate, but neither strikes at the core of the brand Trump has worked to build for decades. At the heart of Trump’s White House bid is the promise that he cannot be bought by Wall Street interests, and that he has the business acumen to be trusted to bring jobs and prosperity back to the United States. Winning is central to Trump’s appeal, as is the seductively lavish lifestyle he has sold to the American public, full of gilded columns and penthouses full of beauty queens and the tremendously classy Trump Steaks. If Trump is unmasked as anything less than “really rich”, as he likes to brag, it could be the one untruth that his supporters could not forgive—or, at the very least, the one lie that causes the rest of his house of cards to come tumbling down. (Hillary Clinton, aware of this possibility, has been preparing similar lines of attack against Trump, and plans to use them against the billionaire all summer.)