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2016 Presidential Debates

Analysis: Pre-Debate 2016, Donald Trump Goes There on Bill Clinton. Now What?

Trump sounds dark note ahead of debate 3:08

Looking to move past a tape that showed him boasting about groping women, Donald Trump held a pre-debate press conference with three women who have accused Bill Clinton of sexual misconduct.

It's worth noting first that the former president has denied the accusations against him and was never charged with any wrongdoing. But a variety of Republicans had long explored — and usually rejected — the idea of bringing up the ex-president's sex scandals in 2016 and attempting to tie them to Hillary Clinton. GOP strategists who conducted polling and focus groups on the topic told NBC News recently that female voters recoiled at any mention of it.

Some argue that the accusations, especially by Juanita Broaddrick, might look worse to young voters who live in a culture more inclined to believe women alleging sexual assault or harassment. Trump campaign manager Kellyanne Conway pointed out on Twitter Sunday that Hillary Clinton had expressed this sentiment herself. (Bill Clinton denied Broaddrick's allegations when they were first made, and Broaddrick initially filed an affidavit saying there was no assault, which she later recanted.)

Others argue there's an opportunity not to focus on Bill Clinton, but on Hillary Clinton for either criticizing women he had affairs with or helping manage scandals surrounding women who accused him of nonconsensual behavior. Most of the evidence comes from vague secondhand accounts, though, with few examples of Clinton publicly disparaging the women in these cases. Trump also brought along a fourth woman, Kathy Shelton, who is tied solely to Hillary Clinton: She defended Shelton's accused rapist in 1975 as a court-appointed lawyer.

On the other side, though there are enormous risks for Trump — and especially Trump — bringing this up.

How will Clinton respond to Trump presser? 2:32

1. He's a terrible messenger for this attack and he's coming from a place of weakness.

Trump is in dire straits politically and his treatment of women is his most immediate problem. There's no way this doesn't look desperate to a lot of people.

Going after Bill Clinton guarantees a prolonged debate over misogyny, which means more segments featuring footage him saying he uses his celebrity status to "grab 'em by the p---y," more speculation over allegations of bad behavior on "The Apprentice," and more coverage of Jill Harth, a woman who accused Trump of groping her in the 1990s (Trump denies the claim and Harth dropped a lawsuit over the issue in 1997.) All this is in addition to the treasure trove of audio and video in which Trump made degrading comments about women, many of them on the Howard Stern show.

If that wasn't bad enough, Trump is on record repeatedly mocking Bill Clinton's accusers. He called Paula Jones a "loser" and complained that the ex-president was unfairly treated over his scandals. So there's an entire hypocrisy angle, with video, that most voters don't even know about yet.

More than a Million Women Share Stories of Sexual Assaults, One Tweet at a Time 1:57

2. It's divisive.

The exact Republicans fleeing Trump are the ones most likely to be dismayed by Trump's latest pivot. He already raised the issue after the last debate and before the 2005 Access Hollywood tape. Republicans appeared to have no appetite for following his lead.

"What the hell are we doing?" one person close to the campaign told NBC News' Hallie Jackson after Trump's pre-debate presser. "It's so stupid. She's the least sympathetic candidate in human history, and if we start going after her husband's infidelity, it makes her sympathetic."

While it could fire up his core supporters, those aren't his problem. The group he needs to worry about most are the moderate women who are most likely to react poorly to this line of attack.

3. It requires discipline that Trump does not have.

Nearly all Republicans who have expressed interest in Trump's latest tack emphasize that it will require a deft touch to keep the focus on Hillary Clinton's behavior vis-à-vis her husband's accusers. Trump's default tool is a wrecking ball that sends a whole lot of debris flying in every direction. It only took a few days of Trump discussing Bill Clinton's scandals after the last debate before he told a screaming rally that Hillary Clinton likely cheated on her husband. He provided no evidence for the claim. The longer Trump stays on the topic, especially while his ego has been bruised by recent events, the more likely he is to say something that damages him further.

McCaskill: 'Trump is angry and defiant' 3:19