And she's largely succeeding. The man who Clinton said at the Democratic National Convention you could "bait with a tweet" is largely taking the bait — and creating potential problems for himself in the process.
Let's break it down.
1) Mark Cuban
Cuban is a very Trumpian figure in his own right — a billionaire with a penchant for making headlines, owning sports teams and hosting reality shows. They have also feuded regularly — despite Cuban initially sounding supportive of Trump's presidential bid.
So when Cuban claimed that he had a front-row seat for the debate, Trump responded by saying that he might invite Gennifer Flowers, with whom Bill Clinton in 1998 acknowledged having extramarital relations in the past.
If dopey Mark Cuban of failed Benefactor fame wants to sit in the front row, perhaps I will put Gennifer Flowers right alongside of him!— Donald J. Trump (@realDonaldTrump) September 24, 2016
And introducing Flowers brought to bear questions about whether Trump might attack Clinton for standing up for her husband in the face of his romantic indiscretions. He didn't do it at the debate, he has begun to publicly muse about doing it — and Rudy Giuliani, a Trump surrogate, argued after the debate that he should have.
2) Alicia Machado
At the very end of Monday's debate, Clinton dropped in the name of a woman Trump is very familiar with: Alicia Machado. Clinton parried an attack on her experience into a discussion about Trump's alleged attacks on women — and she used Machado as Case Study No. 1.
Machado, as most everyone knows by now, was a Miss Universe winner whom Trump publicly shamed for her post-pageant weight gain. She has accused Trump of being verbally abusive, including labeling her "Miss Piggy" and "Miss Housekeeping," because of her accent.
The Clinton campaign soon released a web video that featured Machado and dispatched Machado on a media tour.
By Tuesday morning, Trump was being forced to respond to all of it. And perhaps just as the Clinton campaign had hoped, he doubled down.
"She was the worst we ever had. The worst. The absolute worst. She was impossible," Trump said on "Fox and Friends." "She was the winner, and she gained a massive amount of weight, and it was a real problem. We had a real problem."
It rekindled a long-standing liability for Trump: his past comments about women. They came up at the start of the first GOP primary debate and led to a lengthy feud between Trump and Fox News's Megyn Kelly. By injecting Machado, Clinton breathed new life into the issue, and Trump gladly assisted her in doing so.
3) Questioning Trump's wealth
At Monday's debate, Clinton suggested that Trump isn't turning over his tax returns because "maybe he's not as rich as he says he is."
Then, on Tuesday afternoon at a rally in North Carolina, she offered this:
HRC trolls Trump in Raleigh, NC: "Last night at the debate one of my guests was Mark Cuban. Mark Cuban, who is a REAL billionaire..."— Monica Alba (@albamonica) September 27, 2016
Questions about Trump's wealth are considered a surefire way to get his goat. A Comedy Central writer said earlier this year that it was the one topic that was off-limits in Trump's 2011 roast. Trump even sued a reporter who claimed he wasn't as wealthy as he said. (He lost.)
Cuban himself has gone down this road, questioning Trump's wealth in a June tweet. And Senate Minority Leader Harry Reid (D-Nev.) has done it, too — just last week, in fact.
There is indeed plenty of reason to believe that Trump might be inflating his net worth. Estimates often place his wealth at much lower than the $8-plus billion he has claimed, and he has acknowledged that his estimate is subject to his own feelings and his valuation of the Trump brand.
He hasn't responded directly to this, but it sounds as if Clinton and her allies will keep pushing.
4) Suggesting he doesn't pay taxes
This was in the same response as the he's-not-as-rich-as-he-says comment. And this one drew more of a response.
Clinton suggested that another reason Trump doesn't disclose his tax returns is that he pays no federal income tax. And that isn't a far-out theory; there are ways in which real estate moguls can avoid paying income taxes, and the Trump tax returns that we do have for various reasons show he didn't pay any back then.
When Clinton raised the issue of the returns on Monday night, Trump didn't deny the charge:
CLINTON: Or maybe he doesn't want the American people, all of you watching tonight, to know that he's paid nothing in federal taxes, because the only years that anybody's ever seen were a couple of years when he had to turn them over to state authorities when he was trying to get a casino license, and they showed he didn't pay any federal income tax.TRUMP: That makes me smart.
When Clinton suggested again that Trump doesn't pay income tax, Trump couldn't help but interject, "It would be squandered, too, believe me."
A focus group of undecided voters attended by Post reporter Mary Jordan on Monday night audibly gasped at his first comment. And it's not hard to see it being used in an attack ad.
Trump has often suggested that he gamed the system as a businessman, but he hasn't confirmed that he didn't pay income taxes, which seems like it might be an issue with working-class people who do. Clinton nudged him closer to actually saying it on Monday night. And he cooperated.