Donald Trump Donald John TrumpBubba Wallace to be driver of Michael Jordan, Denny Hamlin NASCAR team Graham: GOP will confirm Trump's Supreme Court nominee before the election Southwest Airlines, unions call for six-month extension of government aid MORE is stepping onto dangerous ground by bringing Bill Clinton William (Bill) Jefferson ClintonGOP brushes back charges of hypocrisy in Supreme Court fight Battle lines drawn on precedent in Supreme Court fight Sunday shows - Ruth Bader Ginsburg's death dominates MORE’s affairs into the race against Hillary Clinton Hillary Diane Rodham ClintonJoe Biden looks to expand election battleground into Trump country Biden leads Trump by 12 points among Catholic voters: poll The Hill's Campaign Report: Biden goes on offense MORE, Republicans say.

Party figures interviewed by The Hill warn the effort won’t grow Trump’s base of support and say he risks further alienating college-educated women who have already been cool to his campaign.

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“The indiscretions, they were done by Bill Clinton, and Trump isn't running against Bill Clinton, which is good for him because Bill Clinton is more popular than Hillary Clinton,” said veteran GOP strategist Charlie Black.



After spending the last week feuding with a former beauty pageant winner over remarks he’s made about her weight, Trump has Republicans worried that he is once again about to embark on an unnecessary and damaging detour.



“He needs to be talking about jobs, immigration and trade,” Black said. “If he talks about those three things, he’ll win. Anything beyond those, he won’t. Nothing is helpful except those three issues. I’m sorry his people have to go out and defend him on this stuff, but they shouldn’t be talking about it, either.”



Trump boasted after the debate that he had steered clear of personal attacks against Clinton out of respect for her daughter, Chelsea Clinton, who was in the crowd.



But he reversed course over the weekend, apparently angered by the barrage of media attention given to a former Miss Universe contestant he had pressured to lose weight in 1996.



The Clinton campaign made Alicia Machado the centerpiece of their campaign last week, and Trump kept the feud alive by attacking Machado's past and defending his remarks.



On Friday, Trump redirected his ire toward Clinton, accusing her of smearing the women Bill Clinton had affairs with in the 1990s.



“Hillary Clinton was married to the single greatest abuser of women in the history of politics,” Trump said. “Hillary was an enabler, and she attacked the women who Bill Clinton mistreated afterward.”



Many Republicans feel the same way, believing Hillary Clinton to be a hypocrite on women’s issues.



Ben Carson, an adviser to Trump who was frustrated by the GOP nominee’s focus on Machado last week, said it’s fine for Trump to raise that point and hit back at Clinton at the next debate on Sunday if he’s attacked as sexist.



But Clinton’s marriage should not become the driving issue of Trump’s campaign, Carson warned.



“Recognizing that many millennials weren’t around, it’s certainly OK to remind people about this or tell them if they don’t know about it,” Carson said. “I think bringing out that hypocrisy can be a good thing to do. But the real issue is what kind of country we’re going to have and whether this will be a people-centric society or a government-centric society. That’s where the two differ sharply, so the affairs should not be the central topic.”



Trump has not broached the issue since a rally on Saturday evening, when he seemed to allege that Clinton had her own affairs, saying she was not "loyal" to her husband.

Trump spent Monday at rallies and forums talking about cybersecurity, military issues and defending his use of tax laws.

But the sensational nature of the charges against the Clintons ensure they’ll get outsized attention.



On Sunday, Trump’s attacks provoked uncomfortable questions for his surrogates, like former New York City Mayor Rudy Giuliani, who was pressed by NBC anchor Chuck Todd about his own past infidelities.



Giuliani said he’s a Catholic and has confessed to a priest.



“I think your bringing up my personal life really is kind of irrelevant to what Hillary Clinton did,” Giuliani said. “She's running for president, I'm not.”



Critics have pointed out that Trump — who has been married three times and whose personal life has been the subject of tabloid fodder for decades — as well as surrogates like Giuliani and Newt Gingrich are imperfect vessels for the family values message.



“This has all gotten really weird, hasn’t it?" said one Republican with ties to the Trump campaign.



Still, the Republican said the issue could help Trump energize his base of supporters to get out and vote against Clinton.



That could be critical in a low-turnout election that might be driven by voter dissatisfaction with two deeply unpopular candidates.



While Trump and Clinton have historically low favorability ratings, polls show Trump is even more unpopular than Clinton, suggesting the GOP nominee has something to gain by further tearing his rival down.



“For the most part, our base would be happy to see him dive into this,” the Republican said. “It could help turn people out in an election where energy is gong to matter.”



Liberals aren’t sweating it in the slightest.



Clinton will have had several weeks to prepare to deal with the attacks by the time Sunday’s debate rolls around.



And Democrats argue that the approval ratings of both Clintons went up after lawmakers on Capitol Hill litigated the issue in the 1990s.



Veteran Democratic operative Joe Trippi said that if anything, bringing up the issue now will engender empathy for Clinton. He and other Democrats are certain Trump will botch the attacks or overplay his hand.



“What spouse, upon finding something out like this, would act kindly toward the other women involved?” Trippi asked. “Like many things he does, this is totally inexplicable and does him no good. I’m fine if he wants to spend as many of the final 37 days talking about this.”



That’s a point where Democrats and many Republicans seem to agree.



“This is the course of action you take when you’re trying to lose an election,” said GOP strategist Brian Walsh. “There’s no adviser around Trump who is recommending this as a good course of action. It takes you off your core message and into a very sensitive issue that would only exacerbate the gender gap at a time when he’s having serious problems getting support from female voters.”