THE MORNING PLUM:

Top Democrats say they’re planning to escalate their attacks on one of the most glaring missteps Donald Trump committed during the debate on Monday night: When confronted over whether he pays nothing in federal taxes, he not only didn’t deny it — he seemed to openly boast about it.

The pro-Clinton Super PAC Priorities U.S.A. is jump-starting the campaign with this new digital ad, that is set to run on Facebook, Twitter, Instagram and Pre-Roll in Ohio, Pennsylvania, North Carolina, and Florida:

In a new digital, pro-Clinton Super PAC Priorities USA released an ad attacking Donald Trump’s comments on taxes Sept. 28. (Priorities USA)

As the ad shows, at the debate, Clinton went out of her way to bait Trump by speculating that one reason he might not want to release his tax returns is that he probably pays nothing in federal taxes. This prompted him to retort: “That makes me smart.”

It’s not clear whether an ad like this will ultimately air on TV, but Justin Barasky, a spokesman for Priorities U.S.A., says this line of attack will be cycled in prominently in various forms, and Clinton surrogates are also set to employ it more frequently.

“While a majority of our efforts will continue highlighting how divisive and dangerous Donald Trump is, the fact that he didn’t pay any money in federal income taxes is an important issue that could break through among all the other noise about him,” Barasky says. “Voters don’t like when you cheat on your taxes, and they certainly don’t like when you brag about how smart you are after admitting you did it.”

It hasn’t been established that Trump cheated on his taxes, and Trump himself has worn this as a badge of honor in the past. During the GOP primaries, Trump also openly boasted: “I fight very hard to pay as little tax as possible.” He justified this by arguing that the government wastes our tax money.

At the time, it was widely argued that voters would not hold this against Trump, since everyone tries to reduce his or her tax burden, and it’s certainly possible that the new Dem assault could fizzle for this reason. However, there is an additional element here — that Trump won’t release his returns — which could raise further suspicions in voters’ minds about just how far Trump has actually gone to lower his taxes.

What’s more, here is another area where Trump is reprising arguments that worked in the GOP primaries but could flop miserably before a general election audience. Earlier this year Trump repeatedly boasted in various forms that he was gaming the system to his own benefit. One additional way he did this, for instance, was to brag repeatedly that he has bought off politicians through campaign donations. He argued that this gave him a level of inside knowledge of how elites scam the system that uniquely positioned him to reform it. GOP primary voters apparently thrilled at his braggadocio, his chest-thumping promise to bust up the elites’ party, and — in the case of his low tax rate — his in-your-face contempt for government.

But this general argument may be running aground in the general election. His boasts about buying off politicians collided with specific allegations of pay-to-play, such as revelations that his charity gave money to a PAC linked to the Florida attorney general at a time when she was entertaining complaints about his Trump University. And now, the boast that he pays nothing in taxes could give Dems a way to further intensify pressure on him to release his returns, and to sow further doubts about his refusal to do so, in the minds of voters who might not be as reflexively anti-government as GOP primary voters are.

Beyond all this, however, there is an element of a trolling exercise about the planned new assault. The goal isn’t just to use this moment to further undercut Trump’s claims to caring about the less fortunate, and to twist the knife on his refusal to release the returns. Another key aim is to try to bait Trump into committing more missteps just like this one. The idea that, when Trump is confronted with the various ways he gamed the system to benefit himself, he simply can’t help but take credit for doing so, since to him, being seen as a winner at all costs — regardless of the means — is paramount.

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* REPUBLICANS WORRY TRUMP WILL COME UNHINGED: With Trump now lashing out at the debate moderator and threatening to go after Bill Clinton’s sex life, the New York Times reports:

The fear among Republicans is that Mr. Trump will confront adversity by continuing to swing impulsively at politically inopportune targets, dragging the party again into needless and damaging feuds, as he did for most of the summer….it could transform the final six weeks of his candidacy into an onslaught of unrestricted personal vituperation — a risky course that would probably please Mr. Trump’s political base at the cost of his broader appeal.

Meanwhile, if Trump does go hard  at Bill, Democrats say they’d welcome an extended battle over character. Can’t imagine why…

* DEMS PLAN TO HAMMER TRUMP OVER DEBATE COMMENTS: The Post previews what’s next in the wake of the debate:

For Democrats, Trump provided…a series of controversial statements and unresolved, damaging questions. He seemed to affirm that he paid no income taxes; he made side remarks and pained expressions while Clinton praised the vibrancy of African Americans; he said it was a smart business strategy to profit from the housing crash….Clinton and a brigade of high-profile surrogates plan to continue using Trump’s debate comments against him.

And one imagines a lot of that stuff will soon show up in TV ads, too.

* TRUMP’S COMMENTS ABOUT NUKES CONFUSE EXPERTS: NBC News reports that experts are flummoxed by Trump’s apparent suggestion during the debate that he would not take the use of nuclear weapons off the table. As one puts it:

“Donald Trump is very cavalier about how he talks about nuclear weapons. He treats them as if they are another tool in the toolbox.”

The confusion, experts noted, stemmed from his apparent lack of knowledge of basic terminology used to describe strictures on the use of nukes. No biggie!

* CLINTON GETS PERSONAL ON THE TRAIL: Politico’s Annie Karni reports that Clinton has decided that contrasting her background with Trump’s (he came from wealthier circumstances) on the trail is key to explaining their differing visions for the country:

In Raleigh, Clinton spoke at length about her mother’s own abused and abandoned childhood, working as a maid and living on her own when she was just 14 years old….The more personal explanation of where Clinton and her husband came from — coming a day after she launched a prime-time assault on Trump’s rich-boy upbringing — doubles as an American dream story, of the Clintons’ rise to the top.

As some Democrats tell Karni, this is a welcome break from the past, when her personal side often seemed hidden from view.
* ARIZONA REPUBLIC ENDORSES HILLARY: Clinton picks up a big surprise endorsement from the Arizona Republic, which argues that her superior temperament, understanding of the complexities of the job and sane position on immigration make her the only choice. Note this:

Since The Arizona Republic began publication in 1890, we have never endorsed a Democrat over a Republican for president. Never. This reflects a deep philosophical appreciation for conservative ideals and Republican principles. This year is different.

There will be a lot more of this. Note, however, that Team Clinton is still not sinking serious resources into contesting the state.

 * ALICIA MACHADO BECOMES A BIG STORY: The Post looks at the emergence in the campaign of Alicia Machado, whose story about being hectored to lose weight by Trump was raised by Clinton at the debate:

Cosmopolitan magazine published a profile of Machado on Tuesday that included photos of her draped in an American flag….Speaking with reporters…Machado recounted how Trump “always treated me like a lesser thing, like garbage.” She said in a mix of Spanish and halting English that she watched the debate with her mother and daughter and cried as Clinton recounted her story.

As noted yesterday, Trump renewed his ridicule of Machado in a post-debate interview, and the question now is whether he’ll continue helping to reinforce the ugliest messages about him.

* AND IF TRUMP’S SUPPORTERS BELIEVE IT, IT MUST BE TRUE: Trump’s false claim that he opposed the war in Iraq got taken apart at the debate, but at a rally late yesterday, Trump found an easy solution to this. He asked the crowd:

“Does everybody believe me, I was against going to Iraq?”

Of course they believe him. And that’s all that matters. Oh, and even if they don’t really believe him, that doesn’t matter, either.